May 1, 2026 - Things to Do

Things to do in Pittsburgh this May

May is here, and so is festival season!

From concerts and culinary events to street fairs and more, here's what's happening around the city this month.

Greek Food Festival | May 5-10 | St. Nicholas, Oakland | Hours vary | Free
Phipps May Market | May 8-9 | Phipps Conservatory and Botanical Gardens | Hours vary | Free
August Wilson Birthday Block Party | May 9 | August Wilson House | 11am-6pm | Free
Toypalooza | May 9 | Monroeville Convention Center | 9:30am-4pm | $10+
Neighborhood Flea | May 10 | SouthSide Works | 10am-3pm | Free
Oakland Restaurant Week | May 10-17 | Times, locations and prices vary
Millvale Music Festival | May 15-16 | Various locations | Hours vary | Free
Strawberry Jell-O Pretzel Salad Standoff | May 16 | The Block Northway | Noon | $12.50
Pittsburgh Power & Fitness Festival | May 16-17 | David L. Lawrence | 9am-5pm | $30+
Pancake Eating Contest | May 17 | Cafe Raymond | 10am-11am | Free

Bruce Springsteen And The E Street Band | May 19 | PPG Paints Arena | 7:30pm | $133+
Pittsburgh Pizza Olympics | May 24 | Spirit | 2pm-8pm | $32
Cultural District Gallery Crawl | May 29 | Various locations | 5:30pm-9pm | Free
PGH Book Fest | May 30 | Carnegie Library, Oakland | 10am-6pm | Free
The Lights Lantern Festival | May 30 | Lawrence County Fair, New Castle | 6:45pm | $45+
Riverlife Chalk Fest | May 30-31 | North Shore | Hours vary | Free

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