
City Cast Philly
☀️ Philly’s best festivals in May
May 1, 2025 · — Siani Colón
Festival season is in full swing and Philly’s making sure you’re outside all spring long. On today’s episode of City Cast Philly, the whole team gets together to share our recommendations for live performances, community markets, and tasty eats for May. If you want even more recommendations, keep reading. ⤵️


What's CITY Talking About?
🍽️ Philly Judge Could Be ‘Witout’ Pay After Promoting Wife’s Cheesesteak Biz
Some of the complaints against Court of Common Pleas Judge Scott DiClaudio – whose wife owns Center City cheesesteak shop Shay’s – include taking a restaurant customer to observe court, hanging articles about his judicial job on the business’s walls, and arguing with negative online reviewers during court hours. The Pennsylvania Judicial Conduct Board rarely takes public action, having only followed up on 58 complaints out of about 800 in 2023, but this is DiClaudio’s second alleged conduct code violation. [🔒The Inquirer]
🌳 Philly Had a Plan To Get More Trees. What Happened?
Former Mayor Michael Nutter wanted Philly to increase its tree canopy by 30% by 2025. Two mayoral administrations later, Philly’s tree canopy only covers 20% of the city. The Philly Tree Plan aims to make the vision a reality, but more education and stable funding sources are needed. [Green Philly]
🎭 New Accessibility Options Are Making Philly’s Performances More Inclusive
Each musical from Ensemble Arts Philly this year had one ASL-interpreted performance, and another offered a sensory-friendly experience with mid-level lighting and a cool-down space. The venues that put on Ensemble Arts productions plan to work with community partners to expand accessibility for disabled community members. [Broad Street Review]
📣 Philly Workers To Rally at May Day Protests
The city announced road closures by City Hall ahead of anticipated crowds for Philadelphia Council AFL-CIO’s “May Day Rally: Workers Over Billionaires" protest and march. U.S. Sen. Bernie Sanders is expected to appear as part of a three-day visit to Pennsylvania in his “Fighting Oligarchy” tour. [City of Philadelphia, 🔒 The Inquirer]
Sponsored Content

Mother's Day Weekend Art Star Craft Bazaar
Shop for handmade goods by over 80 curated craft vendors at our Spring Art Star Craft Bazaar, this Mother's Day Weekend, May 10th and 11th, from 11am-5pm. The event will also include Make + Takes, food/drinks, a free raffle, and free event tote giveaways.

How to Spend May 2025 in Philly

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.
🎭 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.

What To Do
Thursday, May 1
- 👶 Mommy and Baby Yoga/Sensory Play | 9, 10, & 11 a.m. | $25 | Germantown
- 🤓 After Hours Quizzo: Philadelphia, The Revolutionary City | 5:30-8:30 p.m. | Free | APS Museum
- ✂️ Gab And Glue | 6 p.m. | Donation | Old City
- 🧘 Philly River Flow | 6-7:15 p.m. | Donation | Schuylkill River Banks
- 💬 Neighborhood Budget Town Hall | 6-8 p.m. | Free | Oak Lane
- 🍿 “The Good Lyfe” Film Screening & Live Music | 7-10 p.m. | $15 | North Philly
- 🤩 Miss Lisa Lisa's Drag Show | 7:30-9:30 p.m. | $24-48 | Center City
Friday, May 2
- 🛍️ Philadelphia Market Place: Opening Day | Noon - 6 p.m. | Free | Dilworth Park
- 🖤 Warship Olympia Tattoo Arts Convention (Day One) | Noon - 9 p.m. | $20 | Penn’s Landing
- 🌳 Park Clean Up | 3-4 p.m. | Volunteer | Malcolm X Park
- 🎉 First Friday | 4-9 p.m. | Free | Cherry Street Pier
- 📽️ Film Screening: George Nakashima, Woodworker | 5:30-8:30 p.m. | $7-15 | Philadelphia Museum of Art
- 💃 First Friday: Usiloquy Dance Designs & Rini Raghavan | 6-9 p.m. | $35 | Barnes Foundation
- 🤓 LikeMinded-May | 6-10 p.m. | $10-40 | Logan Square
- 🎞️ Producers' Forum with Ashley Tyner and William Tyner | 7-9 p.m. | $4-8 | Scribe Video Center
- ❤️🩹 Healed-ish: Love, Heartbreak & What’s Holding Us Back | 7-10 p.m. | $25 | University City
- 🎤 Monthly Open Mic | 7-10 p.m. | Donation | Kensington
- 🤩 Festival at the Mann 2025: “Maslow’s Peak” | 7:30 p.m. | $25 | Mann Center
- 🍿 Friday Flicks at the Fountain | 7:30-10 p.m. | Free | Parkside
- 🎻 Orchestra Concordia Community Concert | 8 p.m. | Free | Radnor Middle School
- 🌵 Pajamas & Tequila! | 10 p.m. | $15 | Cherry Hill
🎉 How hard do you rep Philly? The Philadelphia Visitor Center is looking for “Phambassadors” to hype up the city leading up to America’s semiquincentennial celebration next year.
Free · Daily