The Hill District was once the heart of Pittsburgh’s jazz scene. Some called it “Little Harlem” or the “Crossroads of the World.”
Between the 1930s and 1950s, The Crawford Grill, a popular club on the corner of Crawford Street and Wylie Avenue, was at the center of it all. Local jazz legends like Mary Lou Williams, Lena Horne, Earl ‘Fatha’ Hines, Billy Strayhorn, and Billy Eckstine performed here — and it’s where national acts like Ella Fitzgerald, Louis Armstrong, and Miles Davis made their Pittsburgh debut.
Our city even played a large role in the development of bebop, a type of jazz known for complex melodies and improvisation. Local artist Kenny Clarke laid the foundation for bebop’s rhythm, and Roy Eldridge helped bridge the gap between swing and bebop styles.
Much of the music stopped when the city razed parts of the Hill District to make room for the Civic Arena, a permanent stain on the city’s relationship with its Black community. While many landmarks are gone, jazz lives on at these bars, clubs, and cultural spaces.
📍Downtown
Nearly every night of the week, you can enjoy global flavors and sounds at Con Alma, meaning “with soul.” Their seasonal menu is perfect for sharing and has a bunch of options for vegetarians. (I’m still thinking about the Korean fried tofu and brussels!) Catch regular jam sessions with sax player Tony Campell, jazz and R&B fusion from “Tempo Noir,” and melodies from vocalists like Erika Denae J.
Mark your calendar for City of Asylum’s annual Jazz Poetry Month celebration in May. (Francesca Dabecco / City Cast Pittsburgh)
📍Chateau
Since 1987, the Manchester Craftsman's Guild has been preserving, presenting, and promoting jazz. Step inside their 350-seat venue to see concerts by both legends and emerging artists. MCG Jazz also boasts K-12 music education, a recording label, and an impressive audio and video archive of performances.
📍Sharpsburg
Transport to a different era at this jazz bar and restaurant inside of an 1930s rowhouse on Main St. Live acts play on Friday and Saturday nights — but the delicious menu of gourmet small plates, carefully selected wines, and handcrafted cocktails runs Wednesday through Saturday. (Sign me up for the handmade tagliolini!)
📍Point Breeze
Did you know there’s a warehouse-gallery loft above Construction Junction? On the second Saturday of each month, see live jazz performers and the Pillow Project’s improv dancers turn the space into a “living canvas of artistic expression.”
MCG Jazz is in its 38th season. (Francesca Dabecco / City Cast Pittsburgh)
📍North Side
Alphabet City at City of Asylum is teeming with smooth tunes every Thursday night. See everything from saxophonists and quartets to composer-improvisors and full orchestras — all for free! Want to check it out before you go? They stream performances online.
📍Highland Park & Riverview Park
Is there anything better than swaying with the music and the trees? Every summer, the Allegheny Regional Asset District helps to put on free jazz shows in Highland Park and Observatory Hill. Stay tuned for the 2025 calendar.
📍Downtown
The August Wilson African American Cultural Center brings world-renowned artists to Pittsburgh’s stage every year. The 15th annual event is Sept. 18-21, and jazz fans in New York and Philly can even take a special Amtrak train to the festival (with live performances on board)!
The music continues! Check for live jazz events at other favorite venues like City Winery and Kingfly Spirits in the Strip District, Mary’s Vine in Rankin, and Golden Age Beer in Homestead.
