Our May Event Guide is here to help Pittsburghers dive into the long-awaited season of festival fun and outdoor experiences. Creativity and culture are in full bloom, with spring markets and festivals, beloved Pittsburgh traditions, neighborhood block parties and much more.
There’s so much more to experience for us to include it all in just just one guide. So be sure to check out our Weekend Event Guides for more things to do all month long. For more art happenings, read NEXT in the Gallery. And don’t miss our Concert Guide coming in early May for the scoop about festivals like Pittonkatonk (May 8-9), Millvale Music Festival (May 15-16) and more.
Pittsburgh Marathon. All photos courtesy of P3R.
1. Pittsburgh Marathon Weekend: May 1-3
It’s a momentous spring for the region, going straight from the NFL Draft to the Pittsburgh Marathon. With 52,000 participants from all 50 states and 25 countries participating, P3R is gearing up for the city’s largest marathon weekend ever. Participants ages 9 months to 88 years — from elite competitors, first-time marathoners and walkers, to handcycle athletes, toddlers and even dogs — will move through the city’s streets spanning 11 exhilarating events.
The excitement kicks off with the free Live Well Expo at the David L. Lawrence Convention Center. Saturday is all about fun for all ages and abilities, with the 5K, Champions Mile, Kids Marathon, Toddler Trot and Pet Walk. The marquee attraction arrives Sunday with a full slate of premier races and a total prize purse of $102,000. It’s a race with a huge heart because the event is expected to raise $1.5 million for charity. Explore the marathon more with Yinzer Backstage Pass. Information.
Claudia Martínez Garay, installation view of “Ghost Kingdom, 2022.” Photo courtesy of On White Wall Studio.
Liz Johnson Artur, installation view of “untitled,” 2021, from the exhibition of life of love of
sex of movement of hope, FOAM, Amsterdam.
Arturo Kameya, installation view of “Whatever comes first,” 2024 at Prospect New Orleans, 2024. Photo by Alex Marks, courtesy of Prospect 6.
Sōfū Teshigahara, installation view at Dalla natura all’arte, 1960, Palazzo Grassi, Venice.
Eric Gyamfi, “Trade winds and shadow objects; north by southeast,” 2021. Red Clay Studio, Tamale,
Ghana.
2. Carnegie International Opening Weekend at Carnegie Museum of Art: May 2-3
An animated journey through the Caribbean seabed. A cargo van carrying work by Haudenosaunee artists. A performance exploring connections between Black steelworkers and dancers. These are just a few of the transformative experiences that await at the 59th Carnegie International. It only comes around once every four years, so don’t miss one of the globe’s most significant presentations of contemporary art.
“If the word we” features new commissions, existing works and projects by 61 artists and collectives, reimagining the museum’s indoor and outside spaces. Accompanied by a major catalog and dynamic public events, this year’s iteration also features collaborations with four partner institutions across Pittsburgh’s cultural ecosystem. Curated by Ryan Inouye, Danielle A. Jackson and Liz Park, the 2026 International aims to be “the most collaborative and far-reaching to date.”
Celebrate Opening Weekend with extended museum hours on Saturday (10 a.m. to 8 p.m.) and Sunday (noon to 8 p.m.). Opening events include G. Peter Jemison’s Barter with Artist program at Carnegie Museum of Art, Torkwase Dyson’s screening “Tomorrow Was Yesterday” at Buhl Planetarium and Sanchayan Ghosh’s workshop at the Children’s Museum. Also don’t miss the Saturday Night Special event at the Mattress Factory and Ross Gay’s performance “Be Holding” at the Thelma Lovette YMCA. The Carnegie International is on view through Jan. 3, 2027. Tickets.
3. Jazz Poetry Month at Alphabet City: May 7-21
For 22 years, this unprecedented exchange of music, language and ideas has brought trailblazing cultural figures to the Burgh for experimentation, collaboration and connection. Dozens of artists will make their way to the North Side cultural hub from near and far to present performances you can’t experience elsewhere. Spanning cultures and genres, programs pair sets by jazz bands with readings and performances from local and international poets.
Don’t miss the kickoff event on May 7, when jazz composer and saxophonist James Brandon Lewis takes the stage with his punk-jazz fusion band, The Messthetics. Joining the quartet will be two City of Asylum Writers-in-Residence. The one-of-a-kind month of improvisational collaboration continues on May 14 when Spanish pianist Marta Sánchez presents an album release concert along with performances by four resident writers. Additional highlights include a concert and book launch on May 21, when multi-disciplinary artist Erika Denae J brings her poetry to life with a 13-piece band. Events are free and can be livestreamed. Add to the experience by making a reservation at the venue’s in-house restaurant, Cucina Alfabeto. Information.
August Wilson Block Party. Photo courtesy of the August Wilson House.
4. August Wilson Birthday Block Party in the Hill District: May 9, 11 a.m.-6 p.m.
On April 27, Pulitzer Prize-winning playwright and Pittsburgh native August Wilson would have turned 81. Now, the public is invited to celebrate Wilson’s remarkable life and legacy at his historic childhood home. The very house where Wilson spent the first 12 years of his life — at 1727 Bedford Ave. in Pittsburgh’s iconic Hill District — will be animated by this free, all-ages block party. For its 10th anniversary, the signature Hill District experience will teem with free activities, including live musical performances, a bustling vendor marketplace, food trucks, children’s activities and interactive entertainment. Guided tours of the house, now a community arts center, will provide attendees with the rare opportunity to “step inside history and connect with the legacy of a storyteller whose work continues to define American theater.” The block party also showcases local entrepreneurs and artists, while underscoring the Hill District’s significant role shaping Black arts and American culture. Information.
Neighborhood Flea. All photos by Nathan J Shaulis / Porter Loves.
5. The Neighborhood Flea at SouthSide Works, May 10, 10 a.m.-3 p.m.
Hurry up and make a dent in your spring cleaning so you can make space for all the treasures you’ll score at The Neighborhood Flea. Kicking off a new season of plein air shopping, the curated pop-up market features 130 vendors selling a fresh mix of vintage collectibles, handmade wares, original artwork and more. Look for jewelry, housewares and textiles, clothing, accessories and baked goods. The dog-friendly event also includes a rotating lineup of local DJs and food trucks. Shopping here means you’re keeping dollars within the community and supporting local independent businesses and creative entrepreneurs. Make it a complete Mother’s Day outing with your mom, auntie or bestie while enjoying brunch at SouthSide Works. Bonus: Use the event’s QR code for discounted rates at the Ladle and Hot Metal parking garages. Information.
Photo by Paul g. Wiegman.
6. Summer Flower Show: Alice’s Adventures in Wonderland at Phipps, May 16-Sept. 27
Slide down the rabbit hole and right into summer. For the brand-new edition of its signature summer flower show, Phipps takes inspiration from Lewis Carrol’s iconic 1865 novel. Bringing scenes from the beloved book to life in every room, the show bursts with interactive elements, fanciful creatures and bizarre botanicals.
Start your unforgettable adventure by watching an animated Alice fall down the rabbit hole in an oversized magic mirror. Meet whimsical topiary characters including a dodo, gryphon and mock turtle, and be mesmerized by a kaleidoscopic sculpture. Join the Mad Hatter for an enchanting tea party and look for the mischievous cheshire cat surrounded by vibrant begonias in a giant tree. Visit the evil Queen of Hearts in her magnificent castle guarded by card soldiers, and stroll amid “marvelous massive and miniature” mushrooms, bugs and flowers. Get curiouser and curiouser with new events offered all summer long, like the Queens of Hearts Royal Tea, Wonderland Family Fun Night and Brunch with Alice in Wonderland. Tickets.
Strawberry Pretzel Salad.
Photo courtesy of YaJagoff. 
Photo courtesy of YaJagoff.
7. Strawberry Jell-O Pretzel Salad Standoff at The Block Northway May 16, 12-2 p.m.
I know I’m not the first Pittsburgher to say this, but my grandmother used to make the most sublime Strawberry Jell-O Pretzel Salad. I also happen to own (but don’t actually use) a copy of the mid-1960s “Joys of Jell-O Cookbook.” Just seeing the recipe name, with its seemingly contradictory ingredients, conjures so much comfort food goodness. Mixing the sweet, the salty, the crunchy and the creamy is a proven winner from the very first bite. Fans of the retro dessert will rally behind their culinary obsession when this unique foodie fest returns to The Block Northway. More than a dozen local eateries will put their own yinzer spin on the irresistible classic, which somehow serves as both a dessert and a side dish. Taste all the addictive entries — from Jenny Lee Bakery and Smashed Waffles to Nothing Bundt Cakes and Grandpa Joe’s — and then cast your vote for the People’s Choice Champion. Tickets.
Photos courtesy of the Allegheny County Parks Foundation.
8. Park ’til Dark and Pour at the Park at South Park: May 16, 6-9 p.m.
Nature and brew lovers alike will come together to support of our region’s nine Allegheny County Parks. Join the Allegheny County Parks Foundation to celebrate 10 years of impactful work surrounded by natural beauty. Setting up shop at South Park’s historic Museum Building and Fairgrounds, the family-friendly fundraiser features tastings of local beer, wine, spirits and NA beverages. Sample mouth-watering offerings from 14 local purveyors, including A Few Bad Apples Cider, Hazel Grove Brewing, Jackworth Ginger Beer, Velum Fermentation and Lucky Signs Spirits. Arrive with an appetite, because food vendors this year are Tocayo Taqueria, Nothing Bundt Cakes and Auntie Anne’s. The one-of-a-kind eco-experience also offers live entertainment by Z-Town Street Band, children’s discovery activities and raffle baskets. Want to do even more to help protect the planet? Roll up your selves and kick off the day at the public tree planting from 1 to 4 p.m. Tickets.
Out of Hand at Contemporary Craft. Photo by Nathan J Shaulis / Porter Loves.
9. Out of Hand: Forest of Delights at Contemporary Craft, May 16, 7-10 p.m.
Step into a “forest of delights” to escape the stress of the daily grind and dance the night away in a blacksmithing studio. Transforming the center’s new Timmons Studios into a “lush world of creativity,” Contemporary Craft’s signature gala offers a vibrant gathering space for friends, artists and supporters in Lawrenceville. Explore creativity as you enjoy open bars, handcrafted bites and decadent desserts, and bid on one-of-kind artwork and curated experiences.
Providing the night’s festive soundtrack will be Kinselland Radio. Event proceeds support free access to exhibitions, resources for artists working with craft materials and dynamic public programs. Pregame the festivities at the new Prelude Reception from 5:30 to 7 p.m., boasting exclusive hors d’oeuvres and cocktails, live cello music and early access to the silent auction. What’s the night’s style board? Gala-goers are encouraged wear their favorite animal print, flower crown or forest-inspired finery. Tickets.
Photo courtesy of the Pgh Book Fest.
10. Pgh Book Fest at Carnegie Library of Pittsburgh – Main (Oakland): May 30, 10 a.m. to 5 p.m.
There’s so much for Pittsburgh’s literary community to love about this year’s Pgh Book Fest. With a larger footprint, expanded opportunities for author access and a participant lineup informed by reader feedback and the library’s most sought-after titles, it’s the place to be for all local bookworms.
Bringing a reader-first experience to the Oakland landmark, the free celebration boasts a “packed slate of panels and author talks across genres, from fan favorites to more niche offerings.” This year’s headlining authors include: Steven Rowley, Catherine Newman, Daniel Kraus, John Scalzi and Meg Medina. During a featured author conversation, Rowley and Newman will discuss “the magic of mundane everyday experiences” found in their works. Highlights include Home is Where the Horror Is, a talk by rising star gothic author Kylie Lee Baker. “Bridgerton” fans will love the Masquerades, Make-outs, and Mischief event exploring the era of popular regency romance books. Don’t miss Burning the Midnight Oil, a talk with authors discussing their academic thrillers, including a story about a prep school in a Pittsburgh suburb. Registration is encouraged.
Photo by Jill Farrar.
11. Attack Theatre’s Thirty Ball at Rockwell Park: May 30, 7:30 p.m.
Dress the part to join Attack Theatre for its pearl anniversary. Revelers will “raise a glass (and maybe a few eyebrows) to 30 years of fearless creativity” and help the homegrown company launch the next 30 boundary-breaking years. Showcasing three fruitful decades of art in the making means that the Thirty Ball is “not your average gala.” Stepping into rooms filled with “people who believe in the power of movement to connect, challenge and inspire,” ball-goers will be treated to immersive live performances and unexpected surprises. Dance through the decades and into the night as the event highlights the company’s evolution from its early “warehouse party days” to its most recent world premiere productions. Tickets.
12. Riverlife Chalk Fest on the North Shore: May 30-31
Kick off summer along Pittsburgh’s riverfronts and make your mark with art when this immersive festival animates the North Shore. Surrounded by our iconic Sister Bridges, Riverlife Chalk Fest brings art right to the ground beneath our feet along Isabella Street, Allegheny Landing and the Three Rivers Heritage Trail. Gather at the river’s edge to watch murals evolve in real time as 24 professional chalk artists from around the U.S. create large-scale works over two days.
Follow the progress, meet the artists and contribute your own designs to community murals. Don’t miss Pittsburgh’s own Chalking Dad (aka Erik Greenawalt) and the Up & Coming artist category spotlighting emerging talent. The free all-ages celebration also features local food vendors, live music and entertainment and hands-on activities. Hop aboard Shore Thing to savor BG Brewing’s Hawaiian-inspired menu on the floating platform anchored off Allegheny Landing. A portion of sales will support Riverlife’s mission to create, activate and celebrate Pittsburgh’s riverfronts. On May 29, Chalk Artist Shawn McCann will lead workshops at the Children’s Museum as part of a special Chalk Preview Day. Festival hours are 2 to 6 p.m. on Saturday and 10 a.m. to 2 p.m. on Sunday. Information.
Bonus events in May
Saturday, May 9: Mother of All Pottery Sales at Union Project, 10 a.m.-4 p.m.
Saturday, May 9: Bealtaine: A Celtic Festival to Welcome Summer at The Pump House, 12-5 p.m.
Monday, May 25: Memorial Day Parade in Lawrenceville, 10 a.m
Monday, May 25: South Hills Memorial Day Parade in Brookline, Dormont and Mt. Lebanon, 10 a.m.