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The Rich Side of Town
In this installment we will look at five East End neighborhoods that form a center of gravity of sorts for the city's wealth: Shadyside, Squirrel Hill, Point Breeze, Park Place, and Point Breeze North. While gentrifying areas may be more attractive to a certain demographic, this part of the East End was the traditional seat of old money, and that is reflected in the neighborhoods' development. To be clear, this isn't a complete list of wealthy areas as much as it is a convenient grouping for the purposes of this series, as I've been trying to group these installments thematically as much as geographically. I could include Regent Square in here as well as it fits both thematically and geographically, and it would tie everything up in a nice little package, but I'm not, because of reasons that I will vaguely hint at until I get to it at the very end of this series.
Series Index:
- Intro
- Downtown
- Strip District
- North Shore
- South Side
- Hill District: Lower Hill
- Hill District: Middle Hill
- Hill District: The Projects
- The Hill’s Environs: Uptown, Sugar Top, and Polish Hill
- Oakland
- Lawrenceville
- Bloomfield, Friendship, and Garfield
- East Liberty
14. Shadyside: Pittsburgh's First Hip Neighborhood
Geographically speaking, Shadyside starts, so to speak, at an indeterminate point on Fifth Ave. somewhere in the vicinity of WQED or the Rodef Shalom Temple where Oakland claims the public landmarks, but the private residences associate with Shadyside. The city puts a hard boundary at Neville St., which is a good general guide, but I've tried to account for the minor colloquial variations. The northern boundary is similarly fuzzy, as the whole Baum-Center area is enough of a no man's land that there was a period in the 80s when some were advocating that it be recognized as a neighborhood unto itself. Despite the similarities, I've given Baum to Bloomfield and Center to Shadyside in this stretch, mainly because Shadyside Hospital is on Center, but that otherwise comes with an asterisk. I hand Center over to East Liberty east of Negley, where the northern border of Shadyside follows the busway ravine until Penn, ending where Fifth and Penn, which ran parallel from Downtown, improbably intersect at Mellon Park. The southern boundary is much more legible; it's officially on Fifth, but as I'm wont to do I run it slightly to the south to give Shadyside both sides of the street.
As much as Pittsburgh's industrial development is associated with the rivers, the city's first experiment with iron smelting occurred about as far from one as you can get. In 1792, a furnace was established in the vicinity of what is now the Winchester Thurston School, the intent of the founders being to produce stove grates. The enterprise only lasted a year before folding due to a lack of charcoal and iron ore, and while the city would later be the nation's capital of steel production, it would be the last industry Shadyside ever saw. In the mid-19th century, Shadyside, like most of the East End, was farmland. Pittsburgh, like all cities at the time, was a walking city, and there was little call for settlement anywhere that wasn't within walking distance of business or industry. After the railroad jumpstarted East Liberty's growth in 1852, it became clear that suburban existence was feasible, particularly for the wealthy, and in 1860, Shadyside Station was established at the northern end of what is now Amberson Ave.
Like the rest of the East End, Shadyside soon became the refuge for professional men who wished to live far from the smoke and squalor of Downtown and the mill districts. The farms were subdivided beginning in the 1860s. At first, larger, irregularly sized lots were sold as mini-estates for business and professional men, but in anticipation of increased demand, Thomas Mellon laid out the old McFarland Estate in the pattern of a traditional urban neighborhood. Development was slow to take off, as commuting costs made the area too expensive for all but the wealthiest. With the arrival of the electric streetcar in 1890, however, it became feasible for the average upper-middle-class professional, and growth exploded. The neighborhood was almost completely built out by 1905.
In the 1910s, the automobile began to present serious competition to the electric streetcar. While this was of little consequence for poor, immigrant-heavy places like Lawrenceville or the South Side, the lack of accommodations for cars presented a serious impediment to Shadyside's status as a neighborhood for the upper and upper middle classes. Even at this early date, newer city neighborhoods like Squirrel Hill and suburbs like Mt. Lebanon were offering amenities like garages and larger lots that were only possible if the houses did not need to be spaced too closely together. By the 1920s, Shadyside appeared to have peaked and was in decline. Larger houses in the western part of the neighborhood were protected by zoning and thus never subdivided, but the same could not be said of the eastern part, which already had several small apartment buildings.
While the decline was limited, one only has to look at an original grand homes and the midcentury infill built next to it to understand that, even if things weren't exactly bad, they were still downscale compared to what they had been previously. This is especially true in the western part of the neighborhood, where massive Victorian edifices stand cheek-by-jowl with positively modest 1950s homes. But it says something that the neighborhood was seeing new construction at a time when the rest of the city was dealing with population loss. Shadyside was still a prime address and the home of some of the city's most prominent citizens, but it was now an accessible address, particularly to Pitt and CMU students who began inhabiting the apartment complexes and divided single-family dwellings in the eastern part of the neighborhood, as well as the newer apartment houses built on the sites of razed mansions along Fifth Ave.
Walnut Street had always contained a business district, but when East Liberty was the retail center of the East End, it was small and scattered and mostly contained the kind of stores that didn’t merit a second glance from anyone who didn't live there—a deli, a hardware store, a grocery store, a movie theater, a drug store, a post office, a pet store, a few bars, and a few coffee houses and bookstores. There were a few destination businesses like William Penn Hat and Gown, which sold what can only be described as "ball-ware", but the street was half residential, and the only people who shopped there were Shadyside residents. In the mid-1950s, the coffee shops began attracting a bohemian crowd, which begat more coffee shops, and the street was dubbed "Espresso Row". Seeing the neighborhood's potential, businessmen Will Shiner and Dick Handler opened a series of live music venues and what had been a sleepy, slightly bohemian neighborhood had become the Place to Be.
In the early 1960s, Shadyside had a sort of triple identity. By reputation, it was the kind of place where guys with beards would spontaneously start playing bongos in a coffee shop. By day, it was still a sleepy neighborhood business district with an unusually high concentration of fine clothing stores, bookstores, and art shops. By night, it was a jumping nightlife spot with packed clubs and movie theaters showing Antonioni's "Blow Up" and other films that couldn't be seen anywhere else in town. Beer, not coffee, was the beverage of choice, and the young men weren't scruffy beatniks but wore jackets and ties. As Shadyside's popularity continued to grow throughout the 1960s, it began attracting a less sophisticated element, and while the neighborhood was far from being sketchy, the more upscale residents began complaining of the hippies moving in. Head shops, waterbed stores, bikers cruising Walnut St., and "bohemian junkies" marked a somewhat seedy period in the late 1960s and early 1970s. Even the movie theater had started showing smut films.
By 1975, however, the action had moved on. Oakland took center stage as the Pittsburgh's happening spot, and things in Shadyside calmed down a bit. There were still a few hangdog places for sure, and the live music scene was still strong, but the overall vibe was more upscale, especially as the first wave of urban pioneers began restoring the Victorian houses. The hippies were slowly becoming yuppies, as was evident in the chi chi boutiques, cocktail lounges, restaurants, and art galleries that proliferated on Walnut St. Demographically, residents included everyone from Richard Mellon Scaife and mayor Pete Flaherty to a diverse collection of professionals, blue collar workers, students, professors, artists, and old-timers. Jane Jacobs would have loved it.
The result, which now seems inevitable, was that Shadyside gradually lost its edge. Chain stores like Banana Republic and The Gap moved in in the late 1980s, driving out many long-time independent merchants. Bars and restaurants in particular were targeted, and Walnut St. became increasingly retail. The smaller merchants initially thought that this would lead to ghettoization, like in nearby East Liberty. The theory was that the business model the chains were operating on—right down to the inflated rents—required the kind of sales that a small neighborhood business district couldn't hope to ever meet. This theory was ridiculous 35 years ago and continues to be ridiculous now, but people still seem to believe it. Every 5 or 10 years a chain store or two closes and it spurs headlines like "Is This the End for Shadyside?" and the local news interviews someone from the Tepper School of Business who offers bland platitudes about the changing retail landscape and people freak out on Reddit about how there are already two vacant storefronts. And within a year those chain stores have been replaced with other chain stores.
14A. The Lay of the Land
I mentioned an East-West divide in the previous section, and while I wouldn't go as far as categorizing them as different sections, there's an obvious transition around Aiken Ave. The street grid west of here is made of large, irregular blocks that contain opulent single-family homes that were never subdivided into apartments. Some of these were originally part of larger estates, but as demand for property grew at the end of the 19th century, developers began looking for ways to maximize the size of house they could fit on a small lot and came up with the dead-end street scheme. Shadyside's dead ends seem like something the neighborhood should be known for, but they instead exist as a historical curiosity. The first of these was Colonial Place, dating from 1897, but the most famous is Roslyn Place, which is celebrated for being the last remaining street paved entirely with wood blocks.
East of Aiken, the neighborhood is more streetcar suburban in feel. This is Shadyside qua Shadyside and contains the Walnut St. business district. From a business perspective, it's still dominated by chains, but there are enough local businesses to keep things interesting. Kards Unlimited, a bookstore/stationer has been continuously operating since 1968, and Mardi Gras, dating from 1954, prides itself for being one of the last Old Shadyside bars. The district's cuteness has led to modern armchair urbanists single it out for that old favorite of mid-century meddlers, pedestrianization. Every so often I hear it described as a "no brainer", or there's an /r/Pittsburgh post titled "Can we turn Walnut into a pedestrian mall already?" And when anyone points out that they already tried that in East Liberty to disastrous results, a chorus of people respond with "This argument has already been debunked! East Liberty only failed because they built a superhighway around it!"
Okay, maybe. I don't think it would be that bad. But here's a cautionary tale: An earlier draft of this installment contained an extensive discussion about the 1992 construction of a parking garage and the longstanding NIMBY opposition thereto. I'll spare you the sordid details, but it was a battle between merchants who insisted that their customers needed parking and residents who had no problem with the customers provided that they didn't build the garage or park on the street in front of their house. They felt that if outsiders wanted to access their exclusive domain they should park in a lot on the outskirts of the neighborhood and take a free shuttle bus in, like the tourists they are.
The online urbanists who advocate for a Walnut St. mall do make some reasonable points to differentiate it from East Liberty. Walnut is not a major thoroughfare with through traffic that would need to be diverted. Cross streets could remain open. The garage can handle whatever on-street parking is lost. The last point may be true, but I lied, nobody ever says that. What they do say is that if suburban tourists want to visit their exclusive urban enclave they can take the bus like true urbanites. Which is funny because there is no bus. You can get within 5 minutes, but there is not direct connection to Walnut St. I don't want to be one of those people who acts like the removal of three on-street parking spaces will sound the death knell for a business district, but the idea that pedestrianization is a good idea in anything other than the limited set of circumstances I outlined in the last installment needs to end. Okay, I promise not to talk about pedestrian malls anymore.
The eastern section of Shadyside also contains most of the apartment buildings and thus is the locus of the neighborhood's student population. While college students from Pitt and CMU have been living here since the 1950s, I can only speak to the motivations of a later generation. In the 2000s, Shadyside was, by far, the most popular neighborhood for grad students. When I enrolled at Pitt law school, my family just assumed I was going to move to Shadyside, because all grad students had to live in Shadyside. I did not move to Shadyside. Nonetheless, this makes sense. While buying a single-family home here requires serious dough, renting here could be surprisingly affordable, especially if you had roommates and were willing to make certain allowances regarding the quality of accommodations. And the bus service to Oakland along Fifth Ave. is nonpareil.
With all of the discussion of Walnut, I would be remiss not to mention that Shadyside has two other business districts as well. The first is along Ellsworth Ave., a street that predates intense development and winds along like the rural lane that it began life as. Like a rural lane, the businesses are more spread out, and traditionally tend more towards galleries and the like, though there used to be a few decent bars here. There was always a business district here, but the development of what architect Joe Indovina called the "not-quite-chic end of Shadyside" began in earnest in the late 1980s as Indovina and other local business owners were hoping to recreate the chill, slightly bohemian neighborhood atmosphere that was lost in the wake of Walnut's yuppification. There's also a business district on South Highland Ave., which is effectively an extension of the East Liberty business district. As such, it was traditionally more downscale than the rest of Shadyside, but when Center and Highland became the nexus of East Liberty's gentrification, gentrified businesses started creeping down South Highland as well. The result is an unusual situation where the business district gets more downscale the further you go into the established old-money neighborhood, and trendier as you move closer to the up-and-coming still-largely-low-income neighborhood.
Finally, a few miscellaneous items I couldn't work in anywhere else. The far eastern end of the neighborhood contains the Village of Shadyside, a New Urbanist community dating from the 1970s that almost gets the architecture correct, and I'm not referring to the notable lack of ornamentation. I don't understand why a lot of these developments go to great lengths to build "contextual" buildings and then put them on curvy roads with front-loading garages. Second, while the neighborhood never went through a true bad period, there were some bad pockets. For example, the Pierce Street Rowhouses were built as servant housing and are accordingly more modest than the rest of Shadyside from that era. By the 1970s, these were largely abandoned but have since been cleaned up and are now more expensive than they were ever intended to be. Finally, Fifth Ave. is a four-lane thoroughfare that lines the southern border of the neighborhood. It was originally lined with the mansions of the rich and famous, but most of these were torn down between the 1920s and 1950s. Midcentury apartment complexes were erected in their place, and these cater mostly to students, particularly Asians, whom I noticed almost exclusively live in managed complexes and not individual units. This section doesn't really have the Shadyside feel to it, but it is right on the bus line to Oakland and is only a short walk to the business district.
Neighborhood grade: Upper middle class. It's the quintessential yuppie neighborhood, but if you can deal with yuppies, Shadyside is a great place to live. But it hasn't been anything approaching "cool" since at least the early '90s. Shadyside has been more or less the same for so long that I think it represents a terminal phase where it stops evolving and starts repeating itself.
I don't want to speculate about how the stasis Shadyside has existed in for the past 35 years might theoretically be disturbed in the future, but the question remains of why it never declined. The obvious answer is that it was always nice, and nothing ever happened that would make it less nice, but that seems lazy and unsatisfactory. There were at least two occasions throughout history when Shadyside could have taken a dive, and it would have seemed logical to the point that I can already envision an alternate history. The first was in the 1920s, when automobiles became popular enough among the upper classes that properties that lacked easy accommodation for them would have seemed anachronistic and down-market compared with the alternatives available at the time. This isn't quite what happened in Friendship, but the parallels are close enough that it's easy to imagine a timeline where Shadyside increasingly became populated by working class residents who still relied on the streetcar for transportation, and the zoning that spared houses the western part of the neighborhood from being converted into apartments was revised in the 1950s, as it was in Friendship. This did happen to a degree, but the effects weren't significant enough to have made much of a mark on history.
The second possibility is that Shadyside's revival as a hip neighborhood could have backfired in the way that many residents feared that it had by the late 1960s. The penalty a neighborhood pays for being The Place to Be is that everyone wants to be there, regardless of whether polite society views them as savory characters. The trends of the early 1960s may have served as a sort of inoculation to this tendency, as jazz and folk clubs, arthouse theaters, and coffee shops weren't known to attract a rowdy crowd. The hippies that replaced them later in the decade were a different story. George Harrison described the disconnect in an interview he did for the Anthology television special. As a cultural elite in London, he viewed the psychedelic movement through the lens of other cultural elites in London and expected the epicenter in San Francisco to be a garden spot for the artistic and political ideas he thought the movement represented. But when he visited the Haight in August of 1967, which by all accounts should have been the height of the Summer of Love, he instead found it to be full of drugged-out teenage runaways who looked more like bums than members of an enlightened youth movement.
I don't want to suggest that Shadyside circa 1970 was anywhere close to Haight-Asbury in terms of how many people it attracted, but it definitely had a seamy side that didn't exist decade earlier. In this alternate timeline, Walnut St. becomes increasingly rowdier throughout the early 1970s, and as the hippie movement subsides, becomes increasingly known as a place to score drugs. Properties close to the business district become increasingly undesirable and occupied by the kind of people for whom proximity to such an area is a plus, and the more respectable establishments close as wealthy people are no longer comfortable going there. The stigma eventually extends to the whole neighborhood, and as the problems of East Liberty get worse in the 80s and 90s, they begin to spill across the tracks along South Highland.
If this seems a bit far-fetched, this is currently what appears to be happening in the South Side. When I did my writeup on that neighborhood two years ago, I graded the neighborhood upper middle class but discussed how a number of high-profile incidents in 2021 and 2022 had sullied the neighborhood's reputation a bit. I wasn't confident in my rating at the time, but I was optimistic that the reputational hit was a consequence of the post-COVID crime hangover and that things would go back to normal once the crime rate went down. This hasn't appeared to have happened. While most of the people complaining about crime in the South Side are the kind of people who wouldn't be caught dead there anyway, the impression that the area is declining hasn't abated. Like most gentrified neighborhoods, the South Side was initially revived by bohemian types, and its heyday was between the mid-90s and the mid 2010s, when Lawrenceville took center stage. To be clear, the South Side's reputation as a rowdy nightlife district precedes it, and crime there was always higher than its reputation would indicate. But one gets the feeling that since the smart set has decamped to Lawrenceville with its more sedate vibe, the only people left who want to party in the South Side or, God forbid, live there, are the kind of people for whom drinking is more than an occasional pastime.
Thus far, high property values have relegated the ne'er do wells to the status of occasional visitors, but they have also pushed out local businesses, except there are no tony chain stores waiting to replace them. Instead, they either sit vacant or attract the kind of disreputable bar owners who see the location as a license to print money and open up the kinds of places that put on an air of exclusivity despite being less particular about their clientele than the average sports bar. The result is limited lifespans and further reinforcement of the perception that the neighborhood is trending downward. It also doesn't help that commercial landlords have thus far not seen the writing on the wall, and continue to charge rents that aren't sustainable for small businesses. While I wouldn't say that vacancies are a problem yet, some properties are sitting empty longer than they should be.
But what about Shadyside? As for the 1920s, it did decline, but it was a gradual decline, and the reinvigoration of the neighborhood in the 1950s arrested that decline at a time when it likely would have otherwise accelerated. The answer to why it didn't decline in the 1970s is more complicated, and requires us to look at its neighbor, Oakland. I don't have any evidence to support this, but it's my theory that the influx in students that Shadyside saw during the 1950s was the result of the changing university landscape after the war. Pitt had heretofore resembled a European university more than an American one; it was an urban "trolley college" where most students commuted from home. Carnegie Mellon (then Carnegie Tech) was more traditional, but only had about 2,500 students, a large proportion of whom went to night school.
In the 1950s, the schools sought to shake this image and increase their on-campus populations. Pitt purchased the Schenley Apartments in 1955 for use as the first dormitories in the school's history. In the meantime, college students looking for an experience as much as an education needed somewhere to live and recreate. Oakland had cultural institutions, but from a residential and commercial perspective, it was still a working-class Italian neighborhood that didn't cater to students. Shadyside was declining but still much nicer and had a lot of old subdivided houses, small apartment buildings, and a small business district that had potential.
By the mid-1970s, though, things in Oakland had changed. More dormitories had been built, the business district had opened bars like the Wooden Keg that explicitly catered to students, and rentals were increasingly available in South Oakland. The natural habitat for what Shadyside was offering in its rowdier days was always going to be closer to campus, and when the ecosystem was in place, the focus shifted. The live music venues of Shadyside's heyday were folk and jazz places; the new places in Oakland were geared toward rock and roll. Shadyside had cocktail lounges, while Oakland had nickel draft nights. On weekday mornings, Walnut St. was filled with rich housewives in mink coats; Forbes Ave. was filled with vomit and garbage.
Shadyside became hip due to its bohemian, intellectual vibe, and only attracted a seedy element due to its sheer popularity. Once the trendsetters decamped for a neighborhood that was more downscale, the rowdy crowd simply followed them there. While we're on the subject, it's worthwhile to look at the fate of Oakland as Pittsburgh's hip neighborhood. It held this status throughout most of the 70s and 80s until it was eclipsed by the South Side around 1994. This was prompted by a dedicated effort by the universities to turn Oakland from a nighttime district into a daytime district, though the rents were already getting too high for low-margin businesses like bars to survive. It would take another decade before Oakland actually lost its edge, but the neighborhood was already too "college" for the new generation of Gen-X hipsters.
It's a bit ironic then that the South Side's popularity was initially also spurred by college students, this time from Duquesne University, whose own neighborhood was too dangerous off campus to attract much student interest. It didn't hurt that just across the 10th Street Bridge lay a working-class neighborhood on the rise that happened to have more liquor licenses per unit area than anywhere else in the city. The South Side's recent downturn is due, in my opinion, to the lack of internal forces that would prevent it. The rowdy crowd was driven out of Shadyside and Oakland at least in part due to the appeal of an alternative that was just as rowdy, if not rowdier. When the millennial hipsters started colonizing Lawrenceville in the mid-2000s, it wasn't because Lawrenceville made more sense location-wise (it didn't make any sense at all), or because the rent got too high, or because there was an institutional force that wanted the South Side bars to close. It was because a generation raised on the South Side wanted a less rowdy alternative.
The people who stayed in Shadyside through the 70s were the same kind of people who moved to Lawrenceville in the 2010s. The bearded, college educated, urban pioneer who can talk about the architectural details he's restoring on his house and would rather see Harold Betters play at the Casbah or Frank Capelli play at Loaves and Fishes than see Joe Grushecky and the Iron City Houserockers at The Decade. And the rich old ladies view him as a pleasant young man, and they don't look askance at the students, who are predominantly of the graduate variety and who may watch football games in bars but aren't drinking for the deliberate purpose of getting drunk and who won't vomit on the sidewalk or light a couch on fire afterward.
15. Squirrel Hill: Nothing Ever Happens
Squirrel Hill is a large neighborhood, the city's largest in both area (over 4 square miles) and population (over 26,000 residents). The city officially divides it into two neighborhoods, North and South, with the dividing line at Forbes Ave., and while there are differences between the two sections, most people don't differentiate unless the occasion calls for additional specificity. Because of its size, Squirrel Hill borders several city neighborhoods—Oakland, Shadyside, Point Breeze, Regent Square, Swisshelm Park, Hazelwood, and Greenfield—but due to being flanked by Schenley Park on the west and Frick Park on the East, and being significantly uphill from Shadyside and Hazelwood, it still feels separated from much of the East End, with only Greenfield and Point Breeze having relatively seamless borders.
Squirrel Hill is the only city neighborhood I've called home, and while I lived there for a long time and loved it, I have surprisingly little to say about it. The underlying goal of this series is to examine neighborhoods in detail with an eye toward change, not in the superficial sense but in a more underlying one, and to examine various aspects of urbanism and the urban environment. The problem here is that for the first 100 years of Pittsburgh's history, nothing happened here. Then the neighborhood was built, and nothing has happened since. Squirrel Hill's rise was late and brief, and its fall hasn't even been hinted at yet.
For the vast majority of the 19th century, the area was nothing but undeveloped farmland, and the wood frame farmhouses that stood there are, as far as I can tell, no longer with us. In 1893, the electric streetcar passed through on its journey from Downtown to Homestead, and there was finally some modest interest in the neighborhood. While some streets, like Murray Hill Ave., were completely built out by 1900, progress was slow. This was in the days when living in such a remote area meant having money, and there were already other more established neighborhoods for the middle to upper classes to call home.
It would not be until the 1920s, and the age of the automobile, that Squirrel Hill would boom. Streetcar suburbs needed to be within walking distance of streetcar lines, and the houses needed to be packed tightly together to maximize the use of space. The automobile came with storage requirements that these neighborhoods weren't in the best condition to accommodate, and as those with the means to afford cars looked for more convenient places to live, Squirrel Hill was next up on the list, so to speak. It was beginning to fill in and had a small business district, but there was plenty of land nearby to build homes with driveways and garages. The neighborhood would become the city's first automotive suburb.
The one notable thing that happened during this period is that Squirrel Hill became the city's premiere Jewish neighborhood. German Jews from the North Side and Homestead had moved to the area as early as 1900, but the heart of Pittsburgh's Jewish community prior to the 1920s was the Hill District. Jews here were less prosperous immigrants from Eastern Europe and began leaving en masse in the 1920s. By 1938, the Hill had lost its place as the center of Pittsburgh's Jewish community as Squirrell Hill, Oakland, and the East Liberty/Highland Park area all saw significant settlement. By 1963, the Jewish populations of Oakland and the East Liberty area had significantly diminished, and Squirrel Hill had firmly become the new centerpiece. I wish there were an interesting story about why they left and why they chose Squirrel Hill, but as far as I can tell they were simply upwardly mobile people looking for more space, and as a newer neighborhood with an existing Jewish population, it was an obvious choice.
Squirrel Hill has, for my entire life, been associated with Judaism to a degree that no other neighborhood in the city is associated with an ethnic group. The neighborhood has never been majority Jewish, but it's remained around 40% for decades, and it's home to about a quarter of Jews living in the Pittsburgh area. Beyond mere numbers, though, it's about visibility. Historically, the commercial district was dominated by Jewish-owned businesses. While this has mostly been lost, largely due to upward mobility (the children of these merchants wanted to become doctors and lawyers, not work in retail), the increasing proportion of ultra-orthodox Jews means that they're more conspicuous than other ethnic groups. Take a stroll down Murray Ave. and the chances of seeing Hasidic Jews who look straight out of central casting are close to 100%.
The first area to see development was the area north of Forbes. Some sections, like the aforementioned Murray Hill Ave., were laid out as streetcar suburbs, but as this part of the neighborhood was one of the wealthier ones in the city and had not been previously settled, auto-oriented residential districts began development early, around 1910. While the generous setbacks would be replicated in postwar suburbia, the architecture is clearly of an earlier era, and the resulting impression is one of miniaturized versions of the estates that lined Fifth at the time. The closest parallel would be the western part of Shadyside, except that the influence of planning is more notable; these are more obviously subdivisions. This is currently the wealthiest part of the city, and it shows. Murdoch Farms is a less celebrated version of Schenley Farms in Oakland, complete with underground electric lines. This section also contains Chatham College, a small school that was all women until recently. The campus is in the middle of a superblock bordered with large estates, and you could live next to it for years without knowing it was there. Hell, I lived in Squirrel Hill for years before I had to visit for work and was surprised that I lived that close to it. The campus has the feel of an opulent park combined with an old money estate and is quite charming.
Moving south of Forbes, the housing becomes more modest, though to what degree depends on which side of Murray you're on. The Jewish merchants who settled in Squirrel Hill in the interwar years were not as wealthy as the Scotch-Irish and German old stock who kicked off the neighborhood's development, and as they preferred to live close to their businesses, the housing surrounding the business district reflects that. If the area north of Forbes is a scaled-down version of a millionaire's estate, the area south of Forbes and east of Murray is a scaled-up streetcar suburb. The urban form is similar, but most of the houses have driveways. West of Murray is notable for containing several areas that were set aside for clusters of small apartment buildings, making it, along with North Oakland, one of Pittsburgh's few historical high-density areas. The housing in the southernmost part of the neighborhood, south of the parkway, is similar in style and age to the northern sections but is distinctly more modest.
The preceding descriptions are generalizations, but one of the great things about Squirrel Hill is that there are always exceptions. The fact that it developed later than other parts of the city and was never part of any housing boom gives it a charming heterogeneity. It was mostly built out by the end of the 1930s, but some of the remote sections saw development into the 1960s. In addition to random streetcar suburban streets without any off-street parking, there are also early 20th century rowhouses, two-flats, and scaled-down postwar dwellings. Some of the more remote sections even have modern quasi-McMansions.There are other areas like this where the lack of consistency makes things look shabby and ad hoc, but the diversity here is more from street to street than lot to lot, and the wealth of the area, even in the less prosperous sections, meant that nothing was built on the cheap.
Tying all of this together is the Forbes–Murray business district. It runs for nearly a mile along Forbes and Murray Avenues with small extensions onto Forward and Shady. I do not think I am engaging in any favoritism towards my former neighborhood by saying that this is the best neighborhood business district in the city. By that I mean that it contains everything you could possibly want in a business district but due to its semi-isolated status it's almost entirely patronized by Squirrel Hill residents. When I lived here, there was a grocery store, movie theater, bowling alley, several banks, several pizza places, a library, a few bars, coffee shops, bakeries, ice cream shops, and countless restaurants. And the restaurants were the kinds of places that just existed, not the kinds of places that won James Beard Awards and got on the Best of Pittsburgh lists.
This has changed somewhat as the neighborhood continues to evolve (the bowling alley has since closed, for example), but the spirit remains, and it's not like Carson St. in the South Side or Butler St. in Lawrenceville where people from across the region will go there for a night on the town. The only two businesses worthy of any outside interest are Dobra Tea, which is a teahouse that operates like a bar and stays open late, and Jerry's Records, possibly the greatest record store on earth. Oh, and there's also the classic, pointless Pittsburgh debate over whether Aiello's or Mineo's has better pizza. The answer is Mineo's, not because they have better pizza (though they do), but because the owners of Aiello's are absolute pricks. The founder was brought over from Italy by the owner of Mineo's, given a job in the pizza shop, and proceeded to steal the recipe and open his own store on the same block. He and his staff threatened me and my roommates on several occasions for bullshit reasons, to the point that I'd spit on the door handle of the manager's $50,000 Nissan Armada (lol) whenever I saw it parked on the street. That same manager, along with everyone working there, were fans of WVU over Pitt and the St. Louis Rams over the Steelers because of Mark Bulger. Then again, when I ordered pizza, I usually got Napoli's because it's just regular pizza that doesn't have to be "The Best".
Neighborhood Grade: Upper Middle Class. At a time when America was flocking to the suburbs en masse, Squirrel Hill was a dense, walkable city neighborhood that still had everything you could want in a suburb, right down to a low crime rate and good public schools. The fact that this was one of the few "nice" parts of the city for so long meant that it was also ridiculously expensive, with people paying top dollar for small, dated (often roach infested) units. With the overall gentrification in the East End over the past 20 years, rents have begun to stabilize, but are still by no means cheap, and buying is off the table for anyone but the independently wealthy.
This is true even in the less desirable far southern part of the neighborhood, for which you pay Squirrel Hill prices without many of the benefits. It's a long walk to the business district or either of the parks, the housing is far more modest, and while Minadeo Elementary is a good school, it isn't as good as Colfax. That being said, it's still incredibly safe, and since you need a car anyway, there are traditional suburban shopping options just across the river in Homestead, so it's not as if it has no appeal.
Much like Shadyside, Squirrel Hill's desirability has been stable to slightly increasing for decades at this point, and I don't see anything changing in the foreseeable future. The only notable demographic change in recent decades is an increasing Asian population. I don't, however, think this represents a true demographic shift so much as the popularity of the apartment districts among Pitt and CMU graduate students who are looking for a more sedate atmosphere than Oakland or Shadyside. I don't see it ever becoming trendy, either, because it is already set up to select for families and other people who deliberately want to live in a nice area that isn't trendy. The Squirrel Cage may be the best neighborhood bar in the city, but it's only notable as the prototypical example of a "regular" bar, and beyond that the bar scene is atrocious. Murray Ave. was also originally residential, and the storefronts were largely tacked onto houses at some point after 1930, meaning that the commercial architecture leaves a lot to be desired. As far as I'm concerned, that's fine, because Squirrel Hill is perfect the way it is, the way it always has been.
16. Point Breeze: Pittsburgh's Most Opulent Neighborhood
Point Breeze lies immediately to the north of Squirrel Hill. The southern and western boundaries of Homewood Cemetery at Forbes and Dallas, respectively, form part of the southern and western boundaries of the neighborhood. The eastern boundary is at Frick Park until the norther boundary near the Reynolds Ave. Gate, at which point it heads north in the vicinity of Braddock Ave. until Penn. The neighborhood to the north, despite being called North Point Breeze, is different enough that Penn certainly feels like a hard boundary when you're driving on it, for reasons we'll look at in the section on that neighborhood. From there, the boundary runs along Shady in the vicinity of Chatham College and then along Wilkins back to the cemetery, but this area is so notably amorphous that it's almost a sub-neighborhood in and of itself, and you have to draw the line somewhere.
Back in Penn Ave.'s pike days, the Point Breeze Tavern stood at what is now the intersection with Fifth. Like most of the East End, the area was farmland well into the 19th century, this particular area being called Homewood, the estate of judge William Wilkins. When the railroad came through around midcentury, Homewood Station was established, and a number of prominent industrialists soon settled in the area south of the railroad tracks. These were the names you learn about in school—Carnegie, Westinghouse, Frick, Heinz. Smaller lots contained the homes of professionals who were associated with these families—for example, the personal physician to the Heinz family had a house on S. Lang—and black servants built more modest accommodations to the north of the railroad tracks. Time for another nomenclature rant. We're still a couple installments away from getting to the present-day neighborhood of Homewood, but for now suffice it to say that the economic fortunes of the area north of the tracks was always distinct from that of the area south of the tracks, and that significant demographic change began to take place around the middle of the 20th century. Some sources claim that the area east of East Liberty was generally known as Homewood prior to the 1950s, and that the wealthy residents of the area south of the tracks began identifying the area as Point Breeze in the 1950s and 1960s to differentiate themselves. To the contrary, I've checked old newspaper articles and real estate listings that identify a distinct Point Breeze district as early as the 1920s. Old maps are inconclusive; Point Breeze is mentioned, but Homewood appears south of Penn, and no boundaries are given. The best I can conclude is that both names were in common usage prior to the 1960s, with Point Breeze generally referring to the areas closer to the intersection of Fifth and Penn. Things didn't get much better in the 1970s, as both the 1974 Community Profiles and 1977 Neighborhood Atlas both use Point Breeze to refer only to North Point Breeze, and lump the rest of the neighborhood in with Squirrel Hill North of Forbes. The first set of boundaries that resemble the current official ones isn't seen until the 1983 Neighborhoods for Living Center map, which doesn't include what is now Park Place. If nothing else, the topic is controversial.
Sticking to the area south of Penn for the time being, at the height of the Gilded Age this district was dubbed "Pittsburgh's Most Opulent Neighborhood", but as that era came to a close, most of these estates were razed, with Frick's Clayton the only one still standing. It's occasionally lamented that this history has been lost, but it was the only realistic outcome given the realities of the time. As American industry became increasingly corporate in the early 20th century, the fortunes of the early industrialists were diluted, with individual heirs only owning a small piece of the estate. The market crash of 1929 turned monstrosities like these into white elephants, and housing shortages associated with increased urbanization made the land on which they sat more valuable than the house itself. Fast forward today, and the wealthy of our own time have no use for these estates either. The architecture may have been interesting, but the interiors would require complete gutting to be compatible with modern lifestyles. This was as true in the 1950s as it was today, and Clayton only survives because it has been turned into a museum, with an art gallery and music hall on the grounds.
The parts of Point Breeze built on subdivided estates are similar to western Shadyside, but on a larger scale. There are more dead-end streets here than anywhere else in the city, and the development of old estates appears to have started in the 1920s and continued into the 1960s. Conversely, the area surrounding Reynolds Ave. was built out as a typical streetcar suburb beginning around 1900, and a similar area was built at the southern end of Lang Ave. later on. The upshot is that Point Breeze has a bit of a patchwork feel to it. West of the cemetery it is an extension of Squirrel Hill north of Forbes, and the streets on the old estates could contain anything from streetcar suburb to interwar suburb to some of the finest examples of residential midcentury modern architecture in the city.
Although it is for the most part a suburban-feeling neighborhood, there are a few small business districts. The most notable one is the block at the western end of Reynolds St., which packs in two restaurants, a coffee shop, a salon, and art gallery, a vintage clothing store, a vet, and several other businesses. I feel like this is one of the more underrated business districts in the city; it has a "cute" feel to it that you can't get in areas that are bigger or swarming with people. Farther east on Reynolds is there is a short row of businesses that includes the Frick Park Market, which Mac Miller wrote a terrible song about and is now full of the kind of tourists who want to visit an unexceptional business that a guy wrote a song about. To be fair to the owners, they haven't tried to cheaply exploit this fame. I don't know much about Mr. Miller, and I could be wrong about this, but when that song came out I got the impression that he was trying to equate the place to a bodega in the hood. If anyone else got this impression, I will inform you that it's a deli in a wealthy part of town, and Mr. Miller's childhood was not lacking. There are also some scattered businesses at the "Five Points" area on Wilkins at the border with Squirrel Hill; this is kind of an indistinct boundary for all practical purposes. Though much of the neighborhood isn't particularly walkable, most people can walk to a business or two.
Neighborhood Grade: Upper middle class. The western part of the neighborhood transitions relatively smoothly into the north of Forbes section of Squirrel Hill and can be thought of as that neighborhood's little brother. It has good schools, tree-lined streets, and an upper middle-class population. The downsides boil down to two things. First, apart from what I just mentioned, there is no real walkable business district. Second, the patchy nature of development on the old estates makes the housing quality uneven. There are some fine specimens, but also plenty of horrible ranches.
While Point Breeze as a whole never went through a bad period, it did suffer an obvious decline as it went from being superwealthy to merely upper middle class. Even through Pittsburgh's darkest days, it was the neighborhood of choice for professionals who were priced out of Shadyside and Squirrel Hill. Though price increases in the past 20 years have eliminated that distinction, there was never much of a distinction culturally between the kind of person who lived in north Squirrel Hill and the kind of person who lived in Point Breeze, and it will continue to be a haven for NIMBY professionals for the foreseeable future. While the current rewrite of the zoning ordinance may change this, residents in the area around Reynolds actually succeeded in downzoning part of the neighborhood where double units were permitted based on fears that student renters would move in. Like Squirrel Hill, I don't think this area will ever be "hot", if it ever was, but it will long be popular for well-off families with children.
17. Park Place: Midwifing a Neighborhood
There's a part of what is officially Point Breeze that's located in a narrow strip between Frick Park and the Wilkinsburg line, bordered by Penn Ave. on the north and Forbes Ave. on the south. For most of its history, maps, guidebooks, news reports, and official pronouncements from city hall have described it as part of Squirrel Hill, Point Breeze, Homewood, or any number of other places. Long time residents simply called the area Frick Park, or, barring that, just gave people directions to their house, only to be met with the response "Where the hell is that?"
The only semi-official evidence I've come across for the area being called Frick Park is on the 1983 Neighborhoods for Living map. It was around this time that residents of this small began insisting on an independent identity, and in 1986 they settled on the name Park Place, taken from the Park Place school, and formed a community group, the goal being to get official recognition from the city. I can't find any evidence for the city's rationale for turning them down, though I suspect that not having their own census tract stacked the deck against them. At some point they did get recognized as a sub-neighborhood of Point Breeze and were listed on a couple blue street signs. However, the ones at the intersection of Forbes and Braddock say Regent Square these days, and the ones at Braddock and Penn don't say anything anymore. There is a Welcome to Park Place sign on Braddock as you head into the neighborhood from the south, but that's all the recognition they get these days.
I had initially intended to just lump Park Place in with the rest of Point Breeze without even giving it its own sub-designation, but after reading about its history of screaming for recognition and being denied, I figure this is the least I can do. It merits its own section anyway, as its history isn't quite the same as Point Breeze. The neighborhood is essentially the eastern counterpart to the streetcar suburb that began developing at the western end of Reynolds Ave. in the 1890s. There are some small parts that sit on subdivided estates, but it's hemmed in on the west by the park, which isolates it somewhat from Point Breeze. On the other side, the street grid slops into Wilkinsburg with no obvious end point. The neighborhood group officially puts the boundary at Trenton St., which has a nice row of businesses, but the border they use includes a lot of midcentury condo and apartment developments that are more common to areas farther east than they are to the core city neighborhood. If I ever finish my discussion of city neighborhoods and get to suburbs, Wilkinsburg is near the top of the list. It has a long history of social and financial incompetence and is half-ghetto and half gentrified. It makes all the sense in the world to merge it into the city, but the local mense lords won't give up their fiefdoms that easily, so it won't happen in the foreseeable future. If that ever happens, I'd extend the neighborhood boundaries into what is currently described as "Greater Park Place". The aforementioned rough patch for Wilkinsburg and Park Place's proximity thereto has meant that historically, this place wasn't as desirable as Point Breeze and only began to turn relatively recently.
Of architectural interest, the neighborhood contains the only examples of Italianate single family homes in the city that I am aware of. There are plenty of Italianate rowhouses and commercial buildings, but few single family homes for some reason. These are clustered on Abbot, Edgerton, and Cromwell Streets, and are some of the first homes in the neighborhood to be built. There's also The Whitehall and Old Heidelberg Apartments, two apartment complexes designed by Frederick Scheibler, Jr. that are, as far as I can tell unique to the city. They eschew the boxy look of most apartment buildings and with their white-gabled facades look more like rambling country villas than urban multifamily residences. This has the effect of blending in with the existing fabric rather than standing out from it. I've certainly seen other buildings try to achieve what this actually does, but in those examples the delineation between units is obvious and trite. Here, it just looks like there are separate entrances to the same house.
Finally, there's the business district, or sort of lack thereof. If we're talking about what's actually in the (semi-) official neighborhood, we're limited to a couple auto-oriented businesses on Penn, including a Walgreens for which the local NIMBYs partially succeeded in scaling back the drive-through plans; Walgreens wanted to take three houses but the damage was limited to one. If we include what's walkable from the neighborhood, there are a couple of businesses on Braddock that are technically in Regent Square but are orphaned from the rest of that neighborhood's business district. And if we're talking what's realistically in the neighborhood and would be if politicians were sane, there's a nice little row of businesses on Trenton Ave. in Wilkinsburg, which the neighborhood group claims but I don't.
Neighborhood Grade: Gentrifying. Not in the sense that it's hot, but in the sense that it's incredibly close to getting the coveted Upper Middle-Class designation but for a couple minor quibbles. The biggest issue is that Braddock Ave. is the psychological boundary where the city stops and Wilkinsburg begins, and it feels surprising to find a pocket city neighborhood east of here. Indeed, since it's more connected to Wilkinsburg than it is to Point Breeze, and that, with one exception, Wilkinsburg has a pretty bad reputation, it feels like this area should be worse than it is, even though for the vast majority of its history it's been a safe, forgotten part of town. With the neighboring parts of Wilkinsburg improving, property values have increased, but it's still less desirable than Point Breeze.
18. North Point Breeze: The Buffer
When Point Breeze began to differentiate itself from Homewood in the 1950s, the railroad tracks served as a definitive boundary between the white, affluent areas to the south and the poorer, blacker areas to the north. Westinghouse Park, located on the grounds of George Westinghouse's former estate, Solitude, was for a long time unofficially off-limits to Homewood residents. Beginning in the 1960s, however, something happened that is, as far as I can tell, unprecedented in urban neighborhoods, and then slowly reversed itself.
The part of North Point Breeze immediately to the south of the railroad tracks had always had a small black population, mostly servants who worked in the estates of the rich and famous. As they had steady employment, they were a bit more well off than blacks in say, The Hill, who were mostly looking for labor wherever they could find it. As black neighborhoods throughout the city began deteriorating following the riots of 1968, well-off black people began looking to escape the neighborhoods where they grew up. For many, this meant the suburbs, or a working-class white neighborhood that was adjacent to the old hood. The usual pattern was that middle class blacks would move in, property values would diminish, allowing lower class blacks to follow them as whites moved out. As the old black hoods turned to full-blown ghettos and blight set it, the ne'er do wells who had turned the old hoods into uninhabitable war zones would gradually filter into these new neighborhoods due to blight-induced housing shortages. By this point the middle-class blacks had moved on to greener pastures, and the process would repeat itself.
When middle class blacks from Homewood began moving into North Point Breeze at the end of the 1960s, one would expect that the area would slowly become ghettoized. In 1970, the neighborhood was about 15% black; by 1990, that had increased to 60%. I don't want to suggest that North Point Breeze did not decline, because it certainly saw diminished property values when compared to Point Breeze proper. And I don't want to suggest that there wasn't a sense that Penn Ave., and not the railroad tracks, was the boundary you should not cross. But North Point Breeze was not a working-class white neighborhood, but an upper middle class one; housing prices would have a lot further to go before lower-class blacks could afford to move in. And while there was some measure of white flight, it was never enough to completely gut the neighborhood. Crime rates were actually lower than in places like Shadyside (which were juicy targets for burglary and car theft), and whites of a more liberal disposition could comfortably move there to show that there was nothing wrong with living among black people.
There's an old saying that it takes a lifetime to build a reputation but only a few seconds to destroy one, and while that may be true for individuals, neighborhoods don't operate like that. While those less attuned to the facts on the ground may harbor outdated ideas about neighborhoods that used to be bad, those same people are also out of touch when it comes to places that aren't as nice as they used to be. What's in a name? A lot apparently. If the black middle class of the 1970s and 1980s sought to claim a neighborhood for themselves, it would have been very tempting for them to reclaim the area for Homewood. Indeed, there was widespread desire to differentiate themselves from the whiter district south of Penn, a desire to welcome Homewood residents to use Westinghouse Park, a desire to demonstrate that they hadn't completely abandoned the black community.
But they chose North Point Breeze, a name that separated themselves from Point Breeze proper without assuming the stigma of Homewood. By the 2000s, prices were on the rise across the East End, and a new generation was living on their own that didn't immediately wince after entering a majority black area. A place is advertised as being in North Point Breeze. Well, Point Breeze is a nice area, right? There may be more black faces than you expect, but they don't look out of place in Point Breeze. And this place is affordable. And so the process reverses itself quickly, and without anyone noticing. Middle class blacks sell out to wealthy whites looking to rehab the old houses. Student renters replace the working poor. By 2020, the area is 60% white, and a mere 25% black, and that's if you include people from 2 or more races. Whatever apprehension anyone may have had about living so close to Homewood dissolves when they realize how much of a barrier the rail line really is, and how the ghetto immediately on the other side has mostly been razed and replaced with affordable housing developments that are selective about their tenants.
North Point Breeze is bounded by Penn on the South, Fifth on the west, the railroad/busway on the north, and the Wilkinsburg line on the east. Like Park Place, there is a section of Wilkinsburg between Penn and the busway that's similar enough in character to the adjacent part of the city that it makes all the sense in the world to include it here, but I won't, because it's a forbearance I simply cannot allow myself (with one exception). It is only four short blocks north to south but extends eight long ones east to west. Like Point Breeze proper, it was home to large estates, but with the exception of the footprint that is now Westinghouse Park, these have since been well-integrated into the street grid, so the neighborhood lacks the dead ends that are characteristic of that neighborhood and the western part of Shadyside.
Initial development of non-estate housing was relatively dense, consisting of semi-detached row houses from the 1880s. Mass development, though, wouldn't start until the 1890s, with the development of the blocks west of N. Dallas Ave. being completely built out by 1900. This was one of Pittsburgh's first true streetcar suburbs, complete with proper boulevards with grassy, tree-lined medians. The eastern portions of the neighborhood continued to be developed through the 1920s, with some scattered infill development continuing until the 1960s. While North Point Breeze went through somewhat of a down period in the 1980s and 1990s, there was never much blight, with the only significant demolition being some houses on Simonton St. that directly faced the railroad tracks.
While there is no proper commercial district, the area east of N. Lexington St. developed as an industrial zone, and most of the old buildings have been repurposed for a mix of uses. The most famous of these is Construction Junction, a warehouse for buying or donating reclaimed building materials. But there is also a climbing gym, Freeride Pittsburgh, the Pitt Archives, a kids gymnastics studio, a martial arts studio, and other similar stuff. There's also a huge complex spanning both sides of Lexington that was recently developed for commercial use, including a new office complex for 3M. As is usual these days, an adjacent lot was supposed to have residential, but people kept insisting that it include affordable housing, so the developer sold it to another developer (presumably because they couldn't get a loan for anything less than market rate), and the whole process started over and hasn't seemed to have made much progress. This is for a development that was announced back in 2017. Finally, this section also includes a small group of rowhouses that haven't seen the same increase in desirability as the rest of the neighborhood. These are mostly occupied by middle-class blacks and, unlike the rest of North Point Breeze, feed into the worst schools in the city.
Neighborhood Grade: Gentrifying. It's getting close, but there's still a mild stigma attached to being north of Penn, and there still more student rentals than in a typical upper middle class neighborhood of such a small size. It also doesn't help that people who visit the businesses in the industrial portion usually describe the area as being part of Homewood. The future is bright, however, and it feels like it's only a matter of time before the distinction between North Point Breeze and Point Breeze only matters as much as the other semi-bogus distinctions the city makes for planning purposes.
That's it for this installment. The next installment won't be quite as thematic, as we'll be looking at three neighborhoods to the north of East Liberty—Highland Park, Morningside, and Stanton Heights—that don't fit into any general category. Since there are only three neighborhoods to cover and I don't anticipate any of them provoking extensive discussion, I'll also look at a couple miscellaneous topics that I've been wanting to cover but haven't in service of keeping the length of these down to the point that I can get them out on a somewhat reasonable schedule.
Transnational Thursday is a thread for people to discuss international news, foreign policy or international relations history. Feel free as well to drop in with coverage of countries you’re interested in, talk about ongoing dynamics like the wars in Israel or Ukraine, or even just whatever you’re reading.
The Wednesday Wellness threads are meant to encourage users to ask for and provide advice and motivation to improve their lives. It isn't intended as a 'containment thread' and any content which could go here could instead be posted in its own thread. You could post:
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Post your project, your progress from last week, and what you hope to accomplish this week.
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