Photo courtesy of the Pittsburgh Pierogi Festival.
Photo courtesy of the Original Pittsburgh Taco Festival.

8. Original Pittsburgh Taco Festival at the Strip District Terminal: September 11

Eat tacos, support the work of the Latin American Cultural Union and Pittsburgh Hispanic Development Corporation. Sounds like a win-win Saturday. Transforming the new Strip District hub into taco town, the foodie fest will showcase 25-plus food trucks, street vendors and eateries, along with live entertainment, special beer, tequila and sangria purveyors, an artist market and family activities. Taste the offerings of the region’s top taco makers such as La Palapa, El Rincon Oaxaqueño, Mi Empanada, Tocayo, Brisketburgh and many others. Providing a festival vibe will be live music from Mariachi Internacional, Karibe Son and Gavas Beat. Buy tickets.

James Brandon Lewis. Photo by Diane Allford courtesy of City of Asylum.

9. Jazz Poetry Month at City of Asylum, September 12-29

Musicians and writers from seven countries around the globe will convene for this once-in-a-lifetime exchange of music, language and ideas. Welcoming back in-person audiences for select live events at Alphabet City, while connecting with artists and audiences around the world via online programs, the 17th annual Jazz Poetry Month will feature nine concerts and four international commissions. It kicks off with violinist and composer Layale Chaker, who will perform a suite of music exploring the sounds, rhythms, rhymes, shapes and forms of Arabic poetry. Artists from Slovenia, North Macedonia, Japan and Estonia will perform in renowned jazz clubs in their home countries. Mai Khoi — City of Asylum’s first exiled musician in residence — will present her “Bad Activist” project. Transcending genre, style and language, the festival empowers musicians and poets to experiment, collaborate and express themselves freely. Register for free.

Photo by Joey Kennedy courtesy of the Pittsburgh International Jazz Festival.

10. Pittsburgh International Jazz Festival at Highmark Stadium & the Benedum: September 17-19

Jazz has long been woven into the DNA of Pittsburgh. The sounds of jazz will again flow live — and provide comfort as the pandemic continues to loom — when the 11th installment of this local festival returns. With legendary, 10-time Grammy Award winner Chaka Khan kicking things off during a concert and after-party, this is one festival you can’t miss. The impressive lineup at Highmark Stadium includes performances from acclaimed vocalist Dianne Reeves; Grammy-winning instrumentalist, composer and producer Marcus Miller; and sax legend Branford Marsalis. Also catch rising jazz stars on the scene such as Gregory Porter, Jazzmeia Horn and Christian Scott aTunde Adjuah. Buy tickets.

11. Sound Series: Block Party on the North Shore: September 18

Forget potlucks and cornhole on your street and instead head to a block party with the best view in town. Launching its return to live, in-person performances, the Andy Warhol Museum’s inaugural Sound Series Block Party will set up shop on Isabella St. along the North Shore. The varied musical lineup features Vieux Farka Touré, Pastor Deryck Tines & the Lemington Chorale, Cassandra Jenkins, Andy Shauf and Dean Wareham, who will perform Galaxie 500’s seminal 1989 album “On Fire.” Marking its 13th anniversary, The Warhol will reprise 13 Most Beautiful…Songs for Andy Warhol’s Screen Tests, which consists of commissioned soundtracks by Wareham and Britta Phillips for a selection of Warhol’s silent film portraits. The outdoor mini-fest will include on-site food and beverage vendors as well as hands-on T-shirt, tote bag and poster-making experiences. Buy tickets.

Photo courtesy of the Great Race and P3R.

12. The Great Race: September 25-26

The starting gun will sound again when the beloved Richard S. Caliguiri Great Race returns to usher in the fall running season. After a year of virtual stats, it’s time to take your place IRL at the starting line. The world-class road race that’s been a Pittsburgh tradition for 44 years on the last Sunday of September has attracted nearly a half-million participants since 1977. Whether you’re a seasoned athlete or a rookie runner, there’s an event just for you — with a 10K, 5K, One Mile Family Fun Run, Tot Trot and Diaper Dash race options in partnership with P3R. Participants will receive a race shirt and medal, and a portion of the proceeds will benefit the Richard S. Caliguiri Amyloidosis Fund. Register now.

Photo courtesy of the Pittsburgh Pierogi Festival.

13. Pittsburgh Pierogi Festival at Kennywood: September 26

Pittsburgh’s favorite amusement park pairs up with Pittsburgh’s favorite food for one mouth-watering day. After eating all the pickles in August, you can eat all the pierogies in September. Whether you like your dumplings cooked the classic church basement way using grandma’s family recipe — or dressed up with a fresh new flavor — you’ll satisfy your pierogi palate. Anything can go inside a pierogi at this imaginative feast — from beer, bacon and jalapeños, to jackfruit, seafood and brisket. Be an adventurous eater and try pierogi cupcakes, pierogi crepes, taco pierogies, pierogi sundaes and smoky rogi sliders. More than 34 vendors will dish out traditional, multicultural and contemporary takes on fall’s perfect comfort food. Attendees will get access to iconic rides such as the Thunderbolt and Noah’s Ark. See why Lonely Planet calls this fest the place to be in the Burgh. Buy tickets.

See more events here.

Jennifer BaronArts & Entertainment / Jobs Editor

Jennifer has worked at the Mattress Factory, Brooklyn Museum of Art and Dahesh Museum of Art and is co-author of Pittsburgh Signs Project: 250 Signs of Western Pennsylvania. She also is co-coordinator of Handmade Arcade. Musically, she is in a band called The Garment District and is a founding member of Brooklyn's The Ladybug Transistor.