
City Cast Pittsburgh
🎸 15 Pittsburgh music festivals
May 7, 2026 · — Francesca Dabecco
Ciao neighbor! An Italian-language version of August Wilson’s play “Jitney” is coming to Pittsburgh this weekend. It’s led by an all-Black Italian cast. How cool?! (👟Use my walking guide to learn more about this famous Pittsburgh playwright.)
🌟 If you appreciate fun tips like this and want to get event recommendations (before anyone else!), become a City Cast Pittsburgh Neighbor.
We’re in the final days of our spring membership campaign and we need 20 new signups today to keep us on track toward our goal.
Grazie in advance 😘

What's CITY Talking About
Gov. Shapiro Sues AI Chatbot Company
Pennsylvania is suing Character Technologies Inc. to stop its AI chatbots from illegally posing as doctors and offering medical advice. This is the Shapiro administration’s first lawsuit against an AI company since it formed a state task force to crack down on chatbots’ potentially harmful messages, especially to children. [Associated Press / Commonwealth of PA]
$1 Million Federal Investment for Downtown Housing
The funding boost will help Pittsburgh’s Urban Redevelopment Authority turn vacant office buildings into affordable housing — an effort the agency has already dedicated $36 million to in recent years. The URA says there are 14 projects in the works for the next four years, which should create nearly 1,000 apartments with around half marked at affordable rates. [KDKA]
- Downtown got a glow up for the NFL Draft. What’s next for the Golden Triangle? [City Cast Pittsburgh]
Pirates All-Star Bob Skinner Dies at 94
The outfielder made his major league debut with the Pirates in 1954 and went on to help Pittsburgh win the 1960 World Series against the New York Yankees. Skinner’s professional baseball career spanned six decades as a player and coach; he was named to the All-Star team three times and earned two World Series rings. [MLB]
Pittsburgh Gets New Orleans Cuisine
Roux Orleans is bringing soul to Chateau on the North Side. Order staples like gumbo, jambalaya, red beans and rice, po’ boys, and more. Food is available for dine-in, takeout, or delivery, but make sure to go early because they sell out! Tip: This new restaurant is located in the same building as my favorite Pittsburgh massage spot. [City Cast Pittsburgh]
Pine-Richland Revises Book Ban Policy
The school walked back its controversial policy that gave the board final say on what books could be included in district libraries. New changes to the policy will limit who can file book challenges to parents or guardians. According to the district, the revisions were created to recognize that there are “diverse viewpoints and strongly held beliefs in our community.” [WESA]
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Discover fun, free events for families!
From May 1 to May 23, Remake Learning Days celebrates its 10th anniversary with hundreds of events for kids, families, and communities. From robot petting zoos and DJ workshops to playful walks through Pittsburgh-area parks, the festival brings kids and families together to wonder, learn, and explore. Find fun, free events for your family at remakelearningdays.org!

Your 2026 Music Festival Lineup

It’s music festival season! Whether you’re into jazz, rock, punk, or folk, Pittsburgh has an event for you. Mark your calendar ⬇️
Loud & Proud Music Festival
June 6
Pride Month just got even more fun! Shop from craft vendors and hear music from regional LGBTQ+ musicians at Allegheny City Brewing in East Allegheny. It will be a day of good vibes, fresh brews, and community camaraderie. All admission proceeds benefit Hugh Lane Wellness Foundation.
WYEP Summer Music Festival
June 27
Grab your lawn chair! You’ll want to snag a spot in Schenley Plaza for WYEP’s Summer Music Festival. This free, outdoor concert is a fun day for the whole family. See the lineup of indie, pop rock, and alternative artists ready to jam out in Oakland.
Northside Music Festival
July 10-12
From emerging local talent to regional headliners, the Northside Music Festival brings together community and good tunes for a free, three-day celebration. Check out music, food, artists, and more in Pittsburgh’s historic East Allegheny neighborhood. Stay tuned for the lineup.
Pittsburgh International Jazz Festival
September 17-20
The August Wilson African American Cultural Center brings world-renowned artists to Pittsburgh’s stage every year at the International Jazz Festival. The multi-day event is a great way to honor our city’s impressive jazz legacy. Can’t wait? See Sean Jones & Friends on June 23 at a fundraiser for the festival.
Four Chord Music Festival
September 25-26
Punk returns to Pittsburgh! Four Chord Musical Festival will rock out at FNB Stadium on the South Side. The independent music fest — a haven for alternative, punk rock, and pop-punk fans — hasn’t been hosted in the city proper since 2019. The lineup drops today.

What To Do
Thursday, May 7
- 🎤 Jazz Poetry at City of Asylum (North Side / Virtual)
- 💡 Radical Trivia at Over the Bar Bicycle Cafe (South Side)
- 🔨 Blacksmithing Basics with Rivers of Steel (Swissvale)
- 🧘 Yoga at Schenley Plaza with 3ROC (Oakland)
- 🌳 Trail Care at Three Rivers Heritage Trail (Hazelwood)
- 🎭 Turning the Page: 50 Years of Pittsburgh Public Theater (Downtown)
- 🎨 WISH Exhibition at Bunker Projects through May 24 (Garfield)
- 👟 East End Pub Run at Bakery Square (Larimer)
- 🖊️ Sip and Script: Calligraphy at The Joinery Hotel (Downtown)
- 🫖 Mother’s Day High Tea at The Frick through May 9 (Point Breeze)
- 🍹 Cocktails With Comrades at 5801 Video Lounge (Shadyside)
- 🎩 We Phantom Figures at Liberty Magic (Downtown)
- ⭐ Hidden History Trivia at Heinz History Center (Strip District)
Friday, May 8
- 🎶 Pittonkatonk in Schenley Park through May 9 (Oakland)
- 🪴 May Market at Phipps Conservatory through May 9 (Oakland)
- 🔥 Women of Steel at The Pump House (Munhall)
- 🪡 Felt & Thread Class with WorkshopPGH (Garfield)
- 🌟 Live Music, Food & More at Carnegie Second Fridays (Carnegie)
- 🛼 Community Party & Skate Night at Allegheny RiverTrail Park (Aspinwall)
- 🍕 Driftwood After Dark at Driftwood Oven (Lawrenceville)
- 🐦⬛ Soft Goth Craft Club at WorkshopPGH (Wilkinsburg)
- 🏥 The George Lucas Pitt Show at Bottlerocket Social Hall (Allentown)
- 🍝 Ravioli Spaghetti Disco at Spirit (Lawrenceville)
- 🚲 Critical Mass Ride starting at Friendship Park (Friendship)
- 💡 Radical Trivia at Trace Echo (Uptown)
- 🎨 Tie Dye Happy Hour with Pittsburgh Sports League (South Side)
- 🪕 Bluegrass at Allegheny City Brewing (East Allegheny)
- ⭐ 21+ Night: Beatlemania at Kamin Science Center (Chateau)
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Shout out to our newest City Cast Pittsburgh Neighbors: Emily R. and Kathy K. (I see you Aunt Kathy! 😉) Thank you for your support!
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