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How to Spend May 2025 in Philly

Posted on May 1, 2025   |   Updated on September 30, 2025

Siani Colón

Maypole dancing on South Street

Brauhaus Schmitz’s annual Maifest Spring Festival will take over South Street on Saturday. And attendees can find more vendors and activities along the corridor that day during South Street Live! (Courtesy of Brauhaus Schmitz)


April showers bring May flowers, and boy is Philly in full bloom this month. We hope you have some comfortable walking shoes, because the city is packed with events throughout May to keep you outside and help you get to know your neighbors, local artisans, and performers.

City Cast

Your Guide to May 2025 in Philly

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Explore the Arts

You don’t have to wait 525,600 minutes to watch this musical. RENT is coming to the Arden Theatre on May 15 and running until June 22. Don’t miss the Tony Award-winning show following the lives of bohemians in New York’s East Village navigating life during the AIDS crisis.

The Philadelphia Latino Arts & Film Festival kicks off May 25 and will continue through July 6. Once a weekend festival, the event has since expanded to six weeks of exhibitions, screenings, and pop-ups.

If you’re looking for some grassroots performances, West Philly will be the place to be on May 31. The West Philly Porchfest will be taking over porches across the neighborhood with over 100 musical acts in a variety of genres. Grab a friend (and maybe a chair and sunscreen) and listen to some free music.

One of Philly’s biggest music festivals is back. The Roots Picnic is taking over the Mann Center on May 31 and June 1. At the top of the festival’s billing are D’Angelo (with the Roots), Meek Mill, and Lenny Kravitz.

Support Philly’s Maker Community

One of the oldest residential streets in the country will be one of the most bustling streets in the city on May 3. Elfreth’s Alley is hosting its annual Spring Makers Market. Shop for artwork, homegoods, and more at this one-day event from 11 a.m. to 4 p.m.

Holding off your planting until May gives your crops a chance to survive that last winter frost. If you’re still deciding what you want in your garden, visit Chestnut Hill’s Home & Garden Festival on May 4.

Just in time for Mother’s Day, find a last-minute gift or shop together at the Art Star Craft Bazaar. The roaming craft fair will be at Cherry Street Pier on May 10 and 11. If you go, say hi to the City Cast Philly team! We’ll be tabling that Saturday.

Come back to Cherry Street Pier the following weekend for Green Philly’s Eco-Fair. Shop for some eco-friendly alternatives while supporting local businesses. The fair is taking place May 17 from noon to 6 p.m.

Go Out and Party

Person performs in front of crowd

Roxborough residents and visitors can listen to live music and support local vendors at the annual Roxborough Spring Festival. (Courtesy of Roxborough Development Corporation)

South Street still knows how to party. South Street Live! is taking over the business corridor on May 3. The block party begins at noon and includes Brauhaus Schmitz’s Maifest, Free Comic Book Day deals, and Queen & Rook’s Fantasy Renn Faire.

Two of Roxborough’s biggest events are coming together for one big party in the neighborhood. Roxborough Spring Festival is back for its 23rd year and joining forces with Rockin’ the Ridge Car Show on May 10. Expect performances from the Philadelphia School of Circus Arts and the West Philadelphia Orchestra, plus more than 70 classic cars and 80 vendors.

On the other side of the city on May 10, the Grassstains Psychedelic Stoop Fest is coming to Lemon Hill Park. From 1 p.m. to 8 p.m., check out local food trucks, live bands, and over 50 vendors.

Show our parks some love! Love Your Park Week is back between May 10 and May 18 to honor Philly’s green spaces. Sign up for a volunteer clean-up, a guided hike, and other nature-based activities throughout the celebration.

If you missed Otaku Fest last month, don’t fret. Video game, anime, and comic book fans are coming together from Philly and beyond for Fan Expo Philadelphia. The three-day event at the Philadelphia Convention Center will feature cosplay competitions, an artist alley, and appearances from John Boyega, John Cena, William Shatner, Manny Jacinto, Pricilla Presley, and Parker Posey. Attendees can purchase a day pass or attend between May 16-18.

Would you climb a greasy pole for some meats, cheeses, and gift cards? You can do that and more at Philadelphia’s 9th Street Italian Market Festival. The street fair celebrates Philly’s Italian pride with music, food, local vendors, and a parade of saints. The festival will take over South Philly on May 17 and May 18.

Wine and Dine

If you can’t make it out to the Philly region’s wineries for a tasting, join the Philadelphia Zoo for the Philly Wine Fest. You can participate in one of two sessions on May 17 between 1 p.m. to 6 p.m. Tickets range from $39 to $55 and guests receive complimentary access to the zoo. You can see the new Galapagos tortoise hatchlings (named after the Golden Girls) while you’re there!

This Guac Off will knock your socks off. Several Philly restaurants are coming together for a friendly competition to raise money for MANNA, which provides meals for people with critical illnesses in Philly and New Jersey. Put some dip on your chip for a good cause on May 22 from 6 p.m. to 9 p.m. at Morgan’s Pier. May the best guacamole win!

What are you looking forward to this May?

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