Over the Hill (District)

Earrings at Ujamaa: $35.
Al’s Special from Grandma B’s: $7.50
Haircut from Big Tom’s Barber Shop: $20

Visit to the Hill District to experience it all: Priceless

Transportation: Accessible via Port Authority Bus System
Location: Centrally located between Downtown Pittsburgh and Oakland
Hours: 24/7
Admission: Free
Accessibility: Handicapped accessible
Both indoor and outdoor site


The Hill District itself has a vast and diverse history. Originally, it housed a population of African American, Italian, and Jewish immigrants in the 19th century. Over the years the Hill District has become a primarily African American neighborhood as Jewish and Italian inhabitants moved to other areas of Pittsburgh.  As the neighborhood’s perimeters were violated and the Lower Hill was overtaken by the city for construction projects (like that of the old Civic Arena) in an attempt to unite the city.

Throughout its history, the Hill District has developed quite the reputation. Although not all of the rumors are true, if you are planning a visit consider going during the day. (This will make it easier to see the amazing murals.) Also, keep in mind that while it is a historical neighborhood with important fictional significance, it’s also home to the people that live there. It is not a museum, it is a neighborhood whose inhabitants might find a camera-obsessed tourist odd. The reputation of the Hill District has remained rough throughout the years but that has not stopped its residents from thriving on their own.

During the mid-1900’s, the Hill District was home to many great and diverse artists, from musicians to authors. The Hill District had a vibrant night life which was enhanced by jazz musicians from around the world. On the author side of the art scene was one of the most well known citizens of the Hill District, August Wilson, a Pittsburgh playwright. Each visitor of the Hill District has their own connection to the space. You can read more about the artistic significance of the Hill District below.

When planning a trip to the Hill District, it may be useful to understand where this neighborhood is located. It is sandwiched between Oakland (to the south and east) and the downtown area of Pittsburgh (to the west). Although the precise limits are not well-defined, it is generally assumed that the Hill District extends from Crawford Street and Herron Avenue and encompasses the following streets: Bedford Avenue, Webster Avenue, Wylie Avenue, and Centre Avenue. As the name suggests, the Hill District sits above its neighboring communities, and the eastern portions of the neighborhood offer extensive views of downtown Pittsburgh.

If you would like to plan your walking tour of the neighborhood beforehand, we recommend an “August Wilson tour” of the Hill District. August Wilson was a successful playwright who was born and raised in the Hill District. Throughout his career he wrote a series of ten plays, nine of which were set in Pittsburgh, that came to be known as the “Pittsburgh Cycle”. He helped to preserve the memories and culture of Hill District residents throughout the 20th century. If you start your visit at the Hill District campus of the Carnegie Library system, you can find a map of the Hill District with markers indicating locations featured in each of the plays. Then, go explore the neighborhood through the eyes of August Wilson!

Jitney Tour from August:

Paper Guide?

When arriving at the Hill District for the first time after reading quite a few pieces of literature on and about it, I had to take it all in. Our personal tour began at Freedom Corner. Freedom Corner is a monument that stands as a celebration of civil rights (a photo has been included below). Standing there I looked down to the city and up to the heart of the district. This was the moment where August Wilson’s writing and reality began to connect. Due to the fact that I read August Wilson: Pittsburgh Places in His Life and Plays by Laurence A. Glasco and Christopher Rawson prior to the tour, all of the descriptions and elements in the guidebook came to life. Our tour was essentially exactly as it is mapped out in August Wilson: Pittsburgh Places in His Life and Plays even though we had a tour guide to help us out along the way. The guidebook was extremely helpful to familiarize yourself with the area before visiting. Also, the book gives August’s connections to all of the stops which gives the tour its own interesting element as compared to strolling around the neighborhood.

Following the Text

Within the text, significant places described in August’s writing are often done so in fictional dialect. Freedom Corner is rightfully placed as the first stop on the tour. The monument give you a good view of not only the downtown area itself, but also the separation between the heart of the city and the Hill District.

Photo Nov 18
Freedom Corner, a monument located at Centre Avenue and Crawford Street,

After leaving Freedom Corner we passed August’s old schools and apartment, along with St. Benedict’s the Moor, until we made it to his childhood home.  When standing in front of the vacant, deteriorating building, I could see Bella’s Market in its former functioning days and a piece of the backyard where pieces that August wrote were set. Standing at 1727 Bedford Avenue, August’s presence in the Hill District began to arise. Not only did August become a famous playwright who centered his plays around Pittsburgh and the Hill District specifically, he also was just another piece of the puzzle that makes up the community of the Hill District. To this day, August Wilson is known by most if not all citizens.  He is one of the most well known figures within the community, which is rightfully so considering the eyes of outsiders that have been opened as a result of his writing.

After leaving 1727 Bedford Avenue, we made our way to the imaginary home of Aunt Esther which is a place that commonly makes an appearance in August’s plays (Glasco).  Our tour then led us to 2046 Wylie Avenue. This is where the Westbrook Jitney Station once stood. Not only was the infamous jitney station location at that address, but also the August Wilson mural was visible from there. The mural is pictured below for a more visual description, but essentially it was painted in celebration of August’s successes. For those who are unfamiliar, a jitney station is basically an illegal taxi service.  It was common in jitney stations for the drivers to be unlicensed with unregistered cars. Jitney stations were necessary in the Hill District because the taxi services themselves would not venture up the Hill on their trips. The Hill District is commonly known for its crime and death rates, so outsiders view it as extremely dangerous. Surprisingly, this system still exists today. There are a few jitney stations still functioning in the Hill District due to lack of other transportation services.

Photo Nov 18
August Wilson Mural located at 2037 Centre Avenue in the Hill District.  This art piece was painted by a variety of artists including Kyle Holbrook and Edward Rawson.


The Westbrook Jitney Station was an integral part in August Wilson’s play Jitney. The play is not only set in the Hill District, but it particularly has a plethora of scenes in the Westbrook Jitney Station. Jitney itself is set in 1977, with a list of characters that follows: Becker, Turnbo, Youngblood, Fielding, Doub, Shealy, Booster, Rena and Philmore (Wilson). These characters range from the man who runs the station, to the jitney drivers, to a reoccurring customer (Wilson). Jitney is not August’s most well known play by any means, but it is extremely relevant to the dynamic of the Hill. Without completely spoiling the play for those who may aspire to read it at some point, the characters endure dramatic event after dramatic event throughout their daily lives. All of the events branch from Becker’s son being released from prison (Wilson). From his return on, the Jitney station and all of the employees trudge through hardships which have the potential to destroy them and their entire lives. The play itself reflects the lives of citizens within the Hill District. With the play in mind while on our tour, I found myself constantly wondering if elements from the play were still relevant. From what I could see and what I heard on our tour, I came to the conclusion that this play is and probably always will be relevant to this community.

The whole idea of jitney stations may seem outdated, but they in fact are still necessary.  There are bus routes that run through the Hill District, but they are very limited.  The jitney stations themselves are scattered throughout the area and still run via phone call from customers. Pictured below is a building that once doubled as both a gas station and a jitney station. This particular jitney station was not the Westbrook station, but it was still  located in Pittsburgh.

Jitney station at Tioga Street and Rosedale Street taken in the 1950’s (Photo taken by Charles Teenie Harris).

The Pittsburgh Cycle

Along with Jitney, August has 9 other plays set in Pittsburgh. These plays describe the lives of African-American’s throughout different centuries (“August Wilson”). The mural, if looked at closely enough, shows the plays and select scenes from them surround August himself. Although Jitney is not the most famous of the cycle, it has its own connection to the history of the Hill as discussed above.

Library Significance

Once taking in all of the outdoors attractions relating to August’s work and wandering past the Westbrook Jitney Station, we made our way to the Carnegie Library of Pittsburgh’s Hill District branch. Inside the library there is a room dedicated to August Wilson containing a collection of all of his plays. Along with the collection, is a map that shows all of the significant places in his writing in correlation to their locations within the Hill District. This map also contributed to the connections that I made personally to the site. Another interesting feature of the library was the stool that August sat on in the Crawford Grille (an old, now closed restaurant in the Hill District). Apparently, when the Grille was in its prime, you could catch August jotting on napkins day after day while on that stool.

Once completing our tour and having a moment to reflect on the spaces and places that we visited, it was clear that August Wilson made quite an impact on the Hill. Although the house at 1727 Bedford Avenue is vacant, the jitney station was demolished and the Crawford Grille has closed, August’s presence remains. The Hill District has a wide history, especially pertaining to August Wilson. August’s significance within the community is no secret. From the room dedicated to him in the library, to the plaque in front of his childhood home, August continues to live on. August just recently passed away in 2005. Although he is gone, his writing continues to represent not only the Hill District, but Pittsburgh as a whole. During my personal visit to the Hill District, I was able to connect what the Hill District and the monuments within his writing were to what the places and things are currently.

I personally feel that it is necessary to give a brief description of what my experience was like without August Wilson connections as a factor. I was traveling through the Hill District with a group, clearly on a tour, and it was obvious I was out of place. I received many confused looks and whispers that were hard to ignore. I feel that it is necessary to give this warning so that potential visitors will not be surprised as they tour. This is easily overlooked when given the opportunity to connect August Wilson’s plays to their real world relations.


The Hill District…and all that jazz!

A young woman celebrates a birthday party at the Crawford Grill in the Hill District. (1930s) “Charlene’s birthday party at the Crawford Grill, with singer Boots Parker and Marion (Courier employee) attending.” Carnegie Museum of Art – Historic Pittsburgh Image Collection. Web. 5 Nov. 2015.

As one walks the streets of Pittsburgh’s Hill District today, it is hard to imagine that it was once a place with a thriving night life. For decades, “The Hill” came alive every night with sounds of jazz floating from crowded clubs through the busy streets. Today, however, many of these venues that produced dozens of jazz greats have closed, and the once thriving neighborhood appears to have lost its shine.

The neighborhood was home to many bars, theaters, clubs, and hotels that hosted late night and early morning concerts for the lively crowds. One such venue was Crawford Grill, originally a three-story, city block-long club in the heart of the Hill District. They attracted a racially and ethnically diverse crowd of audience members eager to listen to talented musicians (Knoch). One longtime resident of The Hill, Lillian Allen, spoke of her memory of the club and its role in her community when she said, “The Crawford Grill was a place to relax over a drink and enjoy good food and jazz” (Glasco 32-33). There were three Crawford Grills throughout its “lifetime”, but visitors today can only imagine the atmosphere; unfortunately, the last of the Crawford Grill locations was closed in the mid 1900s, and its building was destroyed in an urban renewal attempt by the city (“Crossroads of the World”). The building that once was Crawford Grill No. 2, however, is still standing.

The Hill District’s many bars and other music venues hosted famous jazz performers, and so was an important establishment for the reputation of the Hill District. Some of these jazz stars include Duke Ellington, Ella Fitzgerald, and Louie Armstrong! Additionally, many jazz performers began their successful careers in the neighborhood (“Crossroads of the World”). Walt Harper, a famous jazz pianist, was born and raised in Pittsburgh (Palko). After touring with a band for several years after college, he moved back to the city and played at Crawford Grill for years (Palko). Even after the Hill District entertainment scene perished, Harper remained an important musician to the city of Pittsburgh and played at every home Steelers game until 2002 (Palko).

In addition to influencing other jazz musicians, the Hill’s musical atmosphere was important for other artists, such as Pittsburgh’s famed playwright August Wilson. Wilson recognized the significance of jazz in this community:

I wasn’t interested in jazz. [. . .] All that changed on an October night in 1966 when I came up on Kirkpatrick and Wiley Avenue in Pittsburgh and saw about two hundred people standing out on the corner, which was unusual. The first thing I thought was that somebody got killed. So I run down there and I say, “Hey, man, what’s happening?” and they go, “Shhh!” And they were listening to John Coltrane out of the Crawford Grill, you see. And the people inside the Crawford Grill—’cause the drinks cost ninety cents, in ’66 that’s a lot of money—the people inside, they don’t even know how to spell John Coltrane’s name. They inside talking about what they gonna do Friday night and so-and-so’s cousin got a new Lincoln Continental, you see. John Coltrane ain’t playing to them, man, he playing to the brothers out on the street, ’cause the music’s coming straight out over their heads and out on the street. And the brothers outside, they prayin. This is their music. This is what has enabled them to survive these outrageous insults that American society has forced on them.


Jazz has certainly transformed the neighborhood into a complex space. As Edward Soja explained in Thirdspace: Journeys to Lost Angeles and Other Real-and-Imagined Places, defining a space is more complicated than simply identifying one aspect of it; rather, it is a combination of its perceived, conceived, and lived qualities (Soja). The sites of jazz music in the Hill District are not exceptions. First, these places existed in reality; the physical structures that held the stages were real, as were the musicians and their instruments, the sounds of the music, and the smiles and laughter from the audiences. We could have perceived these “empirically measurable” elements at these places and today can even walk along the streets which used to host such events. Moreover, the Hill District had a conceived identity: a community of vibrant diversity, the center of jazz music, an exciting place to be on a Saturday night! The jazz scene reinforced positive connotations about The Hill, and it was a place that attracted musicians from around the country to visit and be a part of the community. Today, that reputation has severely declined; musicians no longer consider The Hill an important jazz community, and the culture of the neighborhood has changed as a result. Finally, it undoubtedly affected the lives of the neighborhood’s residents. Places like Crawford Grill were meeting places for friends to enjoy a night out together or celebrate a birthday, like Charlene in the photo above. Young musicians used the space as a place to get their first gigs as artists and meet their musical idols at concerts. Overall, jazz venues in the Hill District were intricate spaces that fostered growth for the residents. Although the meaning of many of these locations has changed since the early 1900s, the Hill District remains a product of perceived, conceived, and lived experiences.

When urban renewal attempts destroyed the vibrant fabric of this community, it took away a significant piece of the neighborhood’s identity. The existence of clubs like Crawford Grill not only brought musical enjoyment to the community, but it also gave the neighborhood a sense of pride. The Hill District was the center of jazz music in Pittsburgh for decades and helped The Hill maintain a positive reputation among other city residents and visitors. There is hope, however; Crawford Grill No. 2 was recently purchased, and there are plans to restore the club to its original purpose (Glasco 82). One of the investors, Victor Rogue, summed up the significance of the Crawford Grill perfectly: “The history of the Grill is the history of the Hill” (New Pittsburgh Courier Editorial Staff). Perhaps in the future the Hill District will restore the vibrant music scene, and Pittsburghers can dance all through the night, surrounded by the sounds of jazz and dancing.

View of Crawford Grill No. 2 (1960s)
View of Crawford Grill No. 2 (1960s) “View of Crawford Grill No. 2.” Carnegie Museum of Art – Historic Pittsburgh Image Collection. Web. 5 Nov. 2015.



“August Wilson.” Pittsburgh Outdoor Murals and Art. Web. 18 Dec. 2015.

“Charlene’s birthday party at the Crawford Grill, with singer Boots Parker and Marion (Courier employee) attending.” Carnegie Museum of Art – Historic Pittsburgh Image Collection. Web. 5 Nov. 2015.

“Freedom Corner | Pittsburgh, PA 15219 | Pittsburgh PA Tourism.” Visit Pittsburgh. Web. 16 Dec. 2015.

Glasco, Laurence A. and Christopher Rawson. August Wilson: Pittsburgh Places in His Life and Plays. Pittsburgh: Pittsburgh History and Landmarks Foundation. Print.

Harris, Charles Teenie. “Gas Station at Rosedale and Tioga Street.” Historic Pittsburgh. Web. 18 Dec. 2015.

Knoch, Ashley. “Let’s Learn from the Past: The Crawford Grill.” Pittsburgh Post Gazette. Post-gazette.com, 16 Jan. 2014. Web. 5 Nov. 2015.

Lewis, Miles Marshall. Interview with August Wilson. The Believer: San Francisco, CA, Nov. 2004. Web. 13 Dec. 2015

n.p. “Crossroads of the World.” Pittsburgh Music History, n.d. Web. 5 Nov. 2015 < https://sites.google.com/site/pittsburghmusichistory/pittsburgh-music-story/jazz/hill-district>

Palko, Jan. “Ten Noteworthy Jazz Greats With a Pittsburgh Connection.” Popular Pittsburgh, 24 Nov. 2014. Web. 9 Dec. 2015.

Soja, Edward. Thirdspace: Journeys to Lost Angeles and Other Real-and-Imagined Places. Cambridge MA: Blackwell Publishing Inc., 1996.  53-70.

New Pittsburgh Courier Editorial Staff. “Crawford Grill Purchased…Franco Harris Part of Investment Group.” The Pittsburgh Courier, 14 Apr. 2010. Web. 9 Dec. 2015.

“View of Crawford Grill No. 2.” Carnegie Museum of Art – Historic Pittsburgh Image Collection. Web. 5 Nov. 2015.