14+ things to do this weekend, from the Phipps May Market and Pittonkatonk to Skate the Square

What’s going on in Pittsburgh this weekend, May 7-10? Find out here. Know of a cool event? Email us.

Thursday, May 7-Sunday, May 10: Skate the Square in Market Square
4-10 p.m. & 12-10 p.m.
Roller skating around an indoor rink with a disco ball shimmering above you is groovy, but what if you could show off your jamming and carving skills surrounded by skyscrapers Lace up and head to the heart of Downtown Pittsburgh to “Skate The Square.” Produced by the Pittsburgh Downtown Partnership, the skating activation is transforming the newly remodeled Market Square into a pop-up roller rink. The Downtown space is not just for ice skating and farmers markets anymore.

Running through May 25, the first-of-its-kind Burgh pop-up will feature a full-service bar, a rotating lineup of live DJs and plenty of retro vibes. Roll into Downtown to enjoy music, movement and active fun while taking in the energy of Market Square. Don’t miss Thursday’s kickoff festivities from 4 to 10 p.m. Admission: $17 for 75 minutes (includes skate rental). Children under 18 must be accompanied by an adult.
Information.

Thursday, May 7: Jazz Poetry Month Opening Night at Alphabet City
7 p.m.
For 22 years, this unprecedented exchange of music, language and ideas has brought trailblazing cultural figures to the Burgh for experimentation, collaboration and connection. 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, when jazz composer and saxophonist James Brandon Lewis takes the stage with his punk-jazz fusion band, The Messthetics. All Jazz Poetry events are free and can be livestreamed. Read more about Jazz Poetry Month in NEXT.

Friday, May 8, & Saturday, May 9: May Market at Phipps
9 a.m.-7 p.m. & 9 a.m.-5 p.m.
With several late-April frost warnings, anyone who followed the old gardening rule of (green) thumb to wait until after Mother’s Day to plant heeded wise advice indeed. Now that May is here, it’s time to turn over the soil, fire up that weed whacker and sketch out your dream designs because gardening season is here. Mother’s Day weekend is not only for spoiling matriarchs — it’s also for tending to Mother Earth. And the best place to officially welcome the growing season is at this beloved market bursting with quality offerings from 60 local nurseries, farms and vendors.

From organic herbs, vegetable seedlings and tropical plants to succulents, perennials and more — it’s your one-stop shop for digging into spring. You can even stock up on garden accessories, lawn decor, landscaping materials, botanical art, eco-jewelry and organic body care products. Even better? Get pro tips from Phipps horticulturists, owners of local nurseries and local growers. Information.

Friday, May 8, & Saturday, May 9: Pittonkatonk Fundraiser & Festival at the Schenley Park Vietnam Veterans Pavilion
7-10 p.m. & 1-11 p.m.
It’s a spring experience not to miss when this one-of-a-kind Pittsburgh festival transforms Schenley Park’s Vietnam Veterans Pavilion into a vibrant weekend celebration of “culture, community and music.” The homegrown festival marks 13 years of cheering, stomping and honking with bands from around the globe this year. The magical weekend kicks off with Friday night’s Cevapi Dinner Fundraiser. Ticket holders will be treated to an al fresco, family-style dinner featuring the flavors of cevapi (homemade Serbian sausage), paired with an exclusive live performance.

On Saturday, the marquee world music festival fills the green space with community activations and unforgettable performances you can’t see anywhere else. This year’s impressive lineup features legendary Colombian accordion player Yeison Landero and Estonian folk duo Puuluup. Joining them will be national ensembles Undertow Brass Band, Detroit Party Marching Band, Mariposa Galacticas, along with local artists and youth performers. Arrive with an appetite because Pittonkatonk showcases a flavorful lineup of food and drink purveyors, from El Colibri and ShadoBeni to Mr Bulgogi and Goodlander Cocktails. Information.

Friday, May 8-Sunday, May 10: “Shakespeare’s R&J” at City Theatre Company
7:30 p.m. & 2 p.m.
Think you’ve seen every adaptation under the sun of Shakespeare’s iconic “Romeo & Juliet”? Think again. A new adaptation written by Joe Calarco, “Shakespeare’s R&J” is directed by J. Cody Spellman, the John Wells Fellow at Carnegie Mellon University. Via Calarco’s “bold and unconventional” interpretation, Shakespeare’s timeless tale of star-crossed lovers is now told through the lens of four young boys.

Audiences will follow the story of the boys “living under rigid constraints that dictate what they can and cannot read. In an act of rebellion and curiosity, they begin to act out the forbidden text: Shakespeare’s “Romeo and Juliet.” Starring Sam Lander, Silas Bright, Nate Dirksen and Christopher Rone, the play explores a wide range of themes: control, self-discovery, language. forbidden love, vulnerability, liberation and resistance. The production features a collaboration between Carnegie Mellon School of Drama alumni and current students. Tickets.

Saturday, May 9: World Migratory Bird Day at the Frick Environmental Center
9 a.m.-12 p.m.
Did you know that Pittsburgh’s location along the Appalachian Flyway makes it a prime stopover for migrating birds needing to rest and refuel? Be an early bird and flock to the Frick Environmental Center for these avian festivities presented by Pittsburgh Parks Conservancy. With activities spanning the center’s lawn, classrooms and surrounding environment, there’s something for PittsBIRDers of all ages, abilities and interests. During this peak time for spring bird migration, you can hear a dawn chorus, get closeup with birds of prey, discover how beaks are used for feeding and more.

Part of a global initiative to protect migratory bird populations, the free celebration features engaging programming presented in partnership with the National Aviary, Pittsburgh Park Rangers, Bird Lab, Allegheny Bird Conservation Alliance, Carnegie Museum of Natural History and others.

The morning kicks off with the Intersectional Bird Club of Pittsburgh, followed by guided bird walks led by Bob Mulvihill of the National Aviary and local birder Eric Hall. Listen for the songs of migrating warblers and look out for a variety of species as you stroll through one of the region’s top birding destinations.

Highlights include Virtual Bird Banding, Bird Beak Challenge, Egg Matching Game and Discovery Time activities. Learn simple steps for how to make their homes and neighborhoods more welcoming to migrating birds with Allegheny GoatScape, DarkSky International, BirdSafe Pittsburgh and Building New Hope. The city’s youngest birders will love the Junior Garden Buds Storytime and vegetable planting in the From Slavery to Freedom Garden. During the Accessible Birding program, attendees can explore the center’s new Americans With Disabilities Act-compliant Outdoor Discovery Space and Sensory Nature Trail leading to an elevated viewing deck. Information.

Saturday, May 9: Mother of All Pottery Sales at Union Project
11 a.m.-4 p.m.
There are all kinds of mother figures — and this one the takes the top spot when it comes to pottery. Affectionately dubbed the Mother of All Pottery Sales, this colossal celebration of all things clay is a vessel for ceramics, creativity and community. The region’s largest ceramic art market is also the perfect place to score a one-of-a-kind Mother’s Day gift or a functional piece to cherish every day. As you shop for beautifully crafted bowls, mugs, planters and vases, statement jewelry and intricately designed sculpture, you’ll feel good supporting local artists and putting dollars back into the creative economy. Showcasing the best of Pittsburgh’s prolific pottery scene, the market features 45 ceramic artists, including 14 brand-new to the event. It’s not only a place to select handcrafted ceramics and pottery, it’s also a rare opportunity to meet the makers, and check out live clay demonstrations and participate in hands-on activities. With a $20 Early Bird Ticket, you can get a first look at all the wares with one hour of crowd-free, first-access shopping. Information.

Saturday, May 9: August Wilson Birthday Block Party in the Hill District
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.

Free activities, including live musical performances, a bustling vendor marketplace, food trucks, children’s activities and interactive entertainment are a part of the celebration. 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. Read more about the block party in NEXT.

Saturday, May 9: Bealtaine: A Celtic Fire Festival at The Pump House
12-5 p.m.
Head to Homestead to celebrate the midpoint between the spring equinox and the summer solstice. Produced by the Pittsburgh Irish Festival in collaboration with ANAM Arts, the immersive experience will transform the historic Pump House into a dynamic Beltaine festival with a contemporary twist.

The Pittsburgh community is invited to explore this ancient festival “as a living, breathing expression of creativity and connection.” The second installment of the team’s Celtic Fire Festival series, the event follows fresh on the heels of the sold-out Imbolc festival presented in February. With roots dating back to ancient Celtic traditions, Bealtaine (pronounced byal-ten-uh) marks the arrival of summer and the “heightening of light, fertility and creative energy.” Enjoy the richness of Irish and Celtic traditions through movement, music, ritual and shared experiences. Nurturing a spirit of communal gatherings, the event will showcase live music and dance performances, immersive art and cultural activities. Signature highlights include a ceremonial fire experience, hands-on workshops and specialty cocktails inspired by Celtic tradition. Tickets.

Saturday, May 9: A.I.M by Kyle Abraham at the Byham Theater
7:30 p.m.
Trailblazing choreographer and Pittsburgh native Kyle Abraham is celebrating a milestone anniversary with a stop in his hometown. For two decades, A.I.M by Kyle Abraham has “been at the forefront of contemporary dance, becoming one of the most acclaimed touring companies in the world.” Lovers of contemporary dance have only one night to experience this mixed repertory program presented by Abraham’s acclaimed touring company. Abraham’s powerful homecoming performance will close out the 2025-2026 Pittsburgh Dance Council season showcasing the company’s “lush movement, infectious music and magnetic dancers.” Based in New York City, A.I.M performs works by Abraham as well as new and existing works by choreographers who have influenced the choreographer’s artistry. Born in Lincoln-Larimer in 1977, Abraham began dancing when he was young at the Civic Light Opera Academy and the Pittsburgh Creative and Performing Arts High School. Don’t miss the free after‑party open to all attendees in the Byham Theater lobby with Pittsburgh DJ Nate Da Barber. Tickets.

Saturday, May 9: Wynton Marsalis with the PSO at Heinz Hall, “All Rise”
7:30 p.m.
Any fan of jazz music and groundbreaking trumpeter Wynton Marsalis cannot miss this one-night-only performance presented in partnership with MCG Jazz. Part of the Lift Every Voice program, the special production brings together the world-renowned Jazz at Lincoln Center Orchestra with Marsalis, the Pittsburgh Symphony Orchestra led by conductor Benjamin Northey, the Mendelssohn Choir of Pittsburgh with Music Director Daniel Singer, and the Lift Every Voice Unity Choir under the direction of Nikki Porter.

Described as a “genre-bending symphony,” Marsalis’ iconic work fuses musical influences from around the globe, including everything from ancient Greek harmonies, New Orleans brass bands, clave rhythms and classical music, to samba, to jazz, blues and Chinese parade bands. Exploring themes of struggle and redemption, “All Rise” will feature more than 200 artists on stage, performing music inspired by a wide range of world traditions. In the words of Marsalis, the work explores “how [we] will translate our differences into a collective creativity.” Tickets.

Sunday, May 10: Neighborhood Flea Opening Day at SouthSide Works
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. 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. 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. Read more about the Neighborhood Flea in NEXT.

Sunday, May 10: Drag Your Mother To Brunch at The Forge Winery Bar
1-3 p.m.
Pittsburgh’s First Lady of Drag is here to solve an age-old conundrum: “What should we do for Mother’s Day?” Booking a brunch reservation is never a drag when it means your meal is served with a sizzling side of dazzling divas. Head to Homestead to experience a feel-good, family-friendly performance along with brunch catered by Miss TS Tasty Eats. Sure to make the weekend memorable, the Mother’s Day Drag Show features a shimmering lineup of Pittsburgh’s leading drag performers, including Miss Continental Newcomer 2025 Joey Young. This high-energy show will include a mix of live vocals, “fierce lip-syncing” and big helpings of entertainment, style and laughter. Don’t forget to bring cash to tip these talented queens. Tickets.

Special lunch offerings include the BYO Mediterranean Bowls from Jolina’s 2, Loaded Mashed Potatoes from GG’s Express Café and the Caribbean Shrimp Roll Combo from Atarashi Sushi. Chef-driven menus will feature restaurants such as Café Carnegie, Cork & Crust, The University Club and The Porch. Information.

8 more things to do this weekend

Friday, May 8: Lodge in Bloom Fundraiser at the Allegheny Elks Lodge No. 339, 6-9 p.m.

Saturday, May 9, & Sunday, May 10: Nurture in Nature: A Women’s Wellness Retreat at the International Conservation Center, 9 a.m.-7:30 p.m. & 7 a.m.-2:30 p.m.

Saturday, May 9: Toypalooza at the Monroeville Convention and Events Center, 9:30 a.m.-4 p.m

Saturday, May 9: Pennsylvania Brewery Running Series at Aslin Beer Co., 11 a.m.

Saturday, May 9: at Allegheny City Brewing, 1-10 p.m.

Saturday, May 9: Women’s Center & Shelter of Greater Pittsburgh and UPMC Health Plan present Celebrating Survivors at Nova Place, 5:30-9 p.m.

Saturday, May 9: “Bill Nace: Works on Paper” Exhibition Opening at Fungus Books, 6-8 p.m.

More things to do with NEXT: 12 must-do May events, from Chalk Fest to the Carnegie International to the Strawberry Jell-O Pretzel Salad Standoff and NEXT in the Gallery: Preview Pittsburgh summer with a ‘Pity Party,’ dog sculptures and so much more art.