Flowers Meet Fashion: Inspired by Billy Porter opens May 6 at Phipps. Photo by Paul Vladuchick.

May blooms with festivals both brand new and beloved, plus innovative collaborations and never-before-seen exhibits. Whether you’re a bookworm, flea market maven or green thumber, you’ll find so much to do all over Pittsburgh. So run, dance or skip to our top 12 events happening in cool spaces and outdoor places this month.

1. Flowers Meet Fashion: Inspired by Billy Porter at Phipps: May 6

Haute horticulture is spring’s hottest ticket because Phipps is teaming up with megastar and Pittsburgh native Billy Porter. Taking inspiration from Porter’s roots and artistic achievements, the summer flower show is unlike anything in Phipps’ 130-year history. Fashionistas and flora fanatics will be awestruck by room after room of bold botanicals and extravagant costumes. Find colorful fish swimming amidst aquaponics garments, see a shimmering gold costume suspended above water lilies and check out elegant fashions inspired by Porter’s memoir. Strut your stuff in a “Kinky Boots”-themed room and walk the red carpet alongside Oscar-worthy gowns made from plants. To create the unforgettable experience, Phipps enlisted the talents of six fashion designers along with students from Porter’s alma maters, Carnegie Mellon University and CAPA. Buy tickets.

Pittsburgh and the Great Migration: Black Mobility and the Automobile. Photo courtesy of Frick Pittsburgh.

2. Pittsburgh and the Great Migration: Black Mobility and the Automobile at The Frick Pittsburgh: May 6

The Car and Carriage Museum marks its grand reopening with a thought-provoking exhibit exploring the pivotal role that cars played during the Great Migration when 6 million Black Americans left the Jim Crow South for northern cities such as Pittsburgh. The exhibit examines how the automobile facilitated this historical movement between 1910 and 1970 and how Black citizens developed neighborhoods like the Hill District, Homewood and East Liberty. See classic cars like a 1914 Ford Model T, 1939 Buick and 1941 Pontiac Torpedo, vintage clothing and period memorabilia. Don’t miss the 1938 Packard Twelve convertible, similar to one Gus Greenlee drove onto the field during the Pittsburgh Crawfords’ opening day in 1932. Buy tickets.

The Pittsburgh Marathon is also for the dogs. Photo courtesy of P3R.

3. Pittsburgh Marathon Weekend: May 6 & 7

The first weekend in May is synonymous with all things marathon. The fun is not just for elite athletes. With a full and half marathon, relay, 5K, kids marathon, toddler trot and pet walk, everyone from ages 9 months to 90 years can find a race that suits their pace. If running is a spectator sport for you, take your spot in the neighborhood cheer groups and course festivals. And don’t miss the Health & Fitness Expo and the Point State Park Finish Line Festival. New this year is a sensory-inclusive race for kids. Register now.

Steve Schapiro, Warhol, Nico and The Velvet Underground, 1966, © Steve Schapiro, courtesy of Fahey/Klein Gallery.

4. The Velvet Underground & Nico: Scepter Studio Sessions at The Andy Warhol Museum: May 12

On Nov. 9, 2022, the Andy Warhol Museum announced the “discovery and digitalization of the rare master tapes of the Velvet Underground’s debut album.” The news galvanized fans worldwide (this writer included) and shed light on the debut album by Lou Reed, John Cale, Sterling Morrison and Maureen Tucker. One of the most influential albums in music history, “The Velvet Underground & Nico” was released in 1967 on Verve and graced by an iconic peel-away banana cover designed by Warhol, who served as one of its producers. Legendary British musician Brian Eno once said: “The first Velvet Underground album only sold 10,000 copies, but everyone who bought it formed a band,” and we can’t disagree. A must-see for Velvets devotees, this first-of-its-kind exhibit features original master tapes of the nine initial tracks from the band’s first recording sessions in April 1966 at NYC’s Scepter Studios, including alternate versions and mixes. Also on view is never-before-seen footage of the band performing, 30 Warhol Screen Tests and 100 copies of the “banana album.”

May Market at Phipps. Photo by Paul g. Wiegman.

5. May Market at Phipps: May 12 & 13

Fire up the weed wacker, turn over the soil and sketch out your dream designs because gardening season is here. If you follow the gardener’s golden rule of (green) thumb that says to start sewing seeds after Mother’s Day, then this is the planting paradise you’ve been waiting for. It’s a quintessential way to reconnect with Mother Earth right in your own backyard. From organic herbs, vegetable seedlings and tropical plants, to succulents, perennials and seasonal varieties — there’s a staggering selection of 50 vendors. You can even stock up on garden accessories, lawn decor, landscaping materials, botanical art, eco-jewelry and organic body care products. The best part? Get pro tips from Phipps horticulturists, owners of local nurseries and local growers.

Haley Clancy
Poet Haley Clancy. Photo by Miranda Brazinski courtesy of the Greater Pittsburgh Festival of Books.

6. Greater Pittsburgh Festival of Books at Pittsburgh Theological Seminary: May 13

We all know our art scene rocks and our sports teams rule but did you also know that Pittsburgh is home to hundreds of literary organizations, authors and publishers. With a new centralized format, 60-plus featured creators will share their work and creative practice with readers, writers and educators. The event will host a diverse mix of genres ranging from mystery, romance and memoir, to sports, nonfiction and poetry. Featured writers include Jeannette Walls, Ross Gay, W. Bruce Cameron, Leon Ford and J.D. Barker. New this year is a partnership with United Black Book Clubs of Pittsburgh. The free fest also offers activities for kids, including workshops, storytimes, and a hands-on demonstration of Duolingo’s new literacy app. Registration is encouraged.

Image courtesy of Pittsburgh Collage Collective.

7. World Collage Day Extravaganza at the Morningside VFW: May 13

Put down that phone and pick up a pair of scissors. The Pittsburgh Collage Collective is hosting its first-ever World Collage Day Extravaganza. Cutting, pasting and community-building will merge in Morningside where collage enthusiasts can experiment with a variety of DIY and digital techniques and materials. Launched by Kolaj Magazine in 2018, World Collage Day connects makers across global borders and elevates a medium that “excels at bringing different things together to create new art forms and ways of thinking.” Tickets include a hot lunch, workspace, group activities, demonstration stations and raffle prizes.

Work by Christy Culp. Photo courtesy of Union Project.

8. Mother of All Pottery Sales at Union Project: May 13

Pittsburgh’s pottery hub opens its doors for a day of ceramics, creativity and community in Highland Park. The region’s largest ceramic art sale is the ideal place to score a statement piece for your dining room table, a one-of-a-kind gift for Mother’s Day or a functional piece of beauty to enjoy every day. The unique indoor-outdoor event showcases 30 ceramic artists from four states, live clay demonstrations and Raku firing at the kiln shelter. New features this year include the Early Bird Shopping Hour and Coil Pot Contest. Roll up your sleeves and join this clay competition pitting the kiddos against the adults to build the tallest coil pot. Sign up for a free timed slot from 11 a.m. to 4 p.m. or buy an Early Bird ticket for 10 a.m. entry.

Pittsburgh Opera
“We Shall Not Be Moved.” Photo courtesy of Opera Philadelphia.

9. “We Shall Not Be Moved” at the August Wilson African American Cultural Center: May 13-21

Joining forces with Tony Award-winning choreographer, director and dancer Bill T. Jones for the first time, Pittsburgh Opera is once again pushing the boundaries of the art form. Though fictional, the powerful opera draws from — and coincides with the anniversary of — the 1985 MOVE bombing by the Philadelphia Police Department in the city’s Cobbs Creek neighborhood, which destroyed 61 homes, left 250 people homeless and killed six adults and five children. Combining spoken word, contemporary movement and video projections with classical, R&B and jazz vocals, the opera features music by Daniel Bernard Roumain and a libretto by Marc Bamuthi Joseph. Viswa Subbaraman conducts. Buy tickets.

Neighborhood Flea
Neighborhood Flea. Photo by Porter Loves.

10. Neighborhood Flea in the Strip District: May 14

Get that spring cleaning done to make space for all the treasures you’ll score this weekend. Marking its 10th Burghiversary, the fab flea is like having dozens of garage sales all in one place. Bigger than ever, this year’s season boasts more sellers, plus small-batch food purveyors, service providers and coffee vendors. Pickers, thrifters and hagglers will love the chance to peruse everything from vintage goods and upcycled clothing to housewares, collectibles and artisan wares. Animating the open-air market will be live painting, food trucks, music and hands-on workshops. New for 2023 is a free booth for small business owners based in East Palestine, Ohio, and a fundraiser for the town’s community foundation.

Photo courtesy of BikePGH / Murphy Moschetta.

11. OpenStreetsPGH: May 28

Forget sticking to the sidewalks or dodging speeding cars — this is the precious day in Pittsburgh when you rule the roads. Kicking off the season of outdoor fun, OpenStreetsPGH returns by rolling out a brand-new 1-mile addition along the North Shore, where participants can enjoy activities with the Steelers and Pirates, Friends of the Riverfront and Carnegie Science Center. With four hours of car-free fun, you can walk, run, cycle, skate, skip, skip rope or dance right in the middle of the street! This beloved BikePGH event gives residents a new perspective on the city while boosting local businesses. It’s a rare opportunity to make your way from the core of the North Shore to the heart of the Golden Triangle — right through the iconic Armstrong Tunnel minus the autos — then over the scenic 10th Street Bridge into bustling East Carson Street. Along the way, stop at activity hubs for exercise classes, live performances and family activities.

“Emptiness” by chalk artist Alex Maksiov.

12. Pittsburgh Riverwalk & Chalk Fest at Allegheny Landing Park: May 27 & 28

One of the city’s coolest new festivals is taking the chalking and walking fun from the South Shore (last year’s location) to the North Shore. Shake up your routine by spending Memorial Day Weekend along the Allegheny River at Isabella Street — where Allegheny Landing Park and the Pop District intersect. The free festival runs from 1 to 6 p.m. on Saturday and 9 a.m. to 4 p.m. on Sunday. Twenty-three artists from 13 states will descend on the Burgh to conjure eye-popping illusions. This year’s festival goes global welcoming artists from Ukraine, while Pittsburgh’s own Chalking Dad reps our region. Presented by Riverlife, the festival features a CHALKTail Bar with Shorty’s Pins X Pints, mobile eats, live music, street performers and airbrush tattoos.

Find more things to do in Pittsburgh, including public events, live music and family activities, here.

Jennifer BaronEvents & 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.