The Allies Ball
Allies Ball event architect Thommy Conroy designing an experience based on Sir Cecil Beaton and his photographs of the Bright Young Things of the 1920s and 1930s.

8. The Allies Ball and Free for All at Children’s Museum of Pittsburgh: May 21

This year’s benefit bash for Allies for Health + Wellbeing is more critical than ever because the local nonprofit is serving more individuals with far fewer financial resources. Put on something edgy or elegant (or both!) and join the movement to ensure that people living with or at risk of HIV/AIDS can receive life-saving services. The event pays homage to the creative genius of Sir Cecil Beaton, acclaimed for his imaginative photos of British young socialites dubbed the Bright Young Things — known for their outrageous parties and rejection of the status quo. An elegant champagne reception outdoors kicks off the night, along with a presentation of the Kerry Stoner Award to Alan Jones. Next comes a unique dining experience in themed rooms throughout the museum. Gala-goers will then parade to the Free for All party (and it is!) where entertainment from True T Pittsburgh and music by Jellyfish will set the ebullient vibe. Buy tickets.

Photo courtesy of the Pittsburgh Zoo & PPG Aquarium.

9. ZooBrew: Spring Hops at Pittsburgh Zoo & PPG Aquarium: May 27

Where can you sip craft brews, spiked slushees and hard seltzers while getting friendly with a Canadian lynx, Amur tiger and playful sea lions? Party animals of the human kind are invited to bond with all creatures big and small, hop into spring and experience one of the region’s top destinations after-hours. There’s a taste for every beer lover’s palate thanks to the extensive lineup, including 21st Amendment, Lagunitas, Evil Genius, Sobel’s Obscure Brewing and Helltown. Beyond beer, there will be spirits, ciders, sangria, sparkling bevies and even hard coffee for imbibing. From 6 to 9:30 p.m., while sampling the suds and noshing on bites from Taste, zoo-goers will be treated to live music and exclusive access to select animal exhibits and visits. Buy tickets.

Pittsburgh artist Erik Greenawalt aka “The Chalking Dad.” Photo courtesy of the Chalk Art Fest.
Pittsburgh artist Erik Greenawalt aka “The Chalking Dad.” Photo courtesy of the Chalk Art Fest.

10. SouthShore Riverwalk & Chalk Fest at SouthSide Works: May 28

During the pandemic, the chalk art craze swept neighborhoods across the city, with artists of all ages adding imaginative flair to their sidewalks, porches, stoops and patios as they stuck close to home. The art form will reach epic new heights when this first-of-kind festival hits the South Side. Over Memorial Day weekend, 21 prolific artists hailing from 13 states will to take up residence to create eye-popping scenes for all to admire. Works will range from participatory pieces like Sandy Forseth’s chalk mandala to 3-D tableaux by Jan Riggins (Texas) and Kumpa Tawornprom (Florida). Pittsburgh’s own “The Chalking Dad” Erik Greenawalt — featured in NEXT — will rep our city’s local talent. From 2 to 6 p.m., the free festivities will boast food trucks, breweries, music, pop-up performances and hands-on activities, and proceeds will benefit Riverlife. Selfie alert: Artists will begin their street murals on May 27 and onlookers are invited to observe the process.

Photo courtesy of BikePGH and photographer Murphy Moschetta.

11. OpenStreetsPGH Downtown and the South Side: May 29

Is there anything more liberating than feeling the breeze buzz by as you walk, run, skate, or dance in the middle of a city street? Tapping into the spirit of car-free fun as a “vehicle” for community building, this beloved BikePGH event invites you to get an entirely new perspective on city life from 10 a.m. to 2 p.m. If you’ve ever wanted to traverse through the mysterious Armstrong Tunnel or cross the scenic Tenth Street Bridge, now’s your chance. Stretching from Downtown to the Southside, the 2-mile route includes hubs dedicated to health & wellness, arts & culture and kids & families. Check out fitness classes, performances, food trucks, activity stations and special promotions presented by 100 local businesses and organizations. Ready to live on two wheels? Take a Learn to Ride class, maneuver through obstacle courses and master the art of the unicycle. So grab those walking shoes, wheels, blades, decks, yoga mats and four-legged besties and come out to play.

For live music, check out 19 concerts coming to Pittsburgh this May, including Pittonkatonk and the Millvale Music Festival.

For more things to do in Pittsburgh, read 10 can’t-miss events in May for kids, from the Children’s Festival to Remake Learning Days.

Jennifer Baron

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...