Philly Plain Dealer

Below are some cool, fun, and free events to enjoy in May 2026!

Sistah Soul Series at Cherry Street Pier

The Sistah Soul Series includes live music, jam sessions & amazing community vibes. It is a free, all-ages live music experience celebrating soul, jazz, R&B, improvisation, and community connection on the Philadelphia waterfront. Hosted by Shekhinah B.

May 1st – 6pm – 9pm

Philadelphia Film Society – Community Screenings – Film Society Center 

May 1 – 6:30pm – Like Water For Chocolate

Community Screenings are free events curated in partnership with Philadelphia arts and advocacy organizations.

Free Community Boating at FDR Park

May 2nd, 9th & 30th – 10am – 1:30pm 

Free Community Fishing at FDR Park

Every Wednesday from 4pm – 6:30pm

Bridging Blocks: Library Events

Bridging Blocks was created to help residents build the skills to engage in civic dialogue while breaking down echo chambers.

May 2nd, 9th, 11th, 12th, 19th, 20th & 28th

RECESS

An immersive performance created by Odean Pope and Immanuel Watkins that transforms a North Philly warehouse into a sculptural playground of sound!

May 3rd & 10th – 3pm – 1835 W Oxford St, Philadelphia, PA, 1921

The Nationals at National Mechanics

A weekly open-call drag and performance competition upstairs at National Mechanics.

May 4th and 11th at 8pm 

Bok Movie Club

May 4th – Bok Auditorium – 7pm

Film: Repo Man

5 De Mayo Block Party

Sueño is taking over the streets for a massive 5 de Mayo block party. Expect a full day of Latin energy in Center City with a lineup of DJs, Mexican street food, and plenty of drinks. Curated by Latin Vibes Group, this is a proper neighborhood takeover from afternoon till evening.

May 5th – 9th Street // 4pm-9pm

Local College Baseball – UPenn, Saint Joe’s, La Salle

There are many college sports programs in Philadelphia that do not get any shine! College baseball is an untapped mine of talent and good times. Go check out these teams and 

La Salle – 5/8, 5/9, 5/10
SJU – 5/1, 5/2, 5/3, 5/8, 5/9, 5/10
UPenn – 5/1, 5/2, 5/3

Northern Liberties Spring Festival

A full day of family fun with live music, local vendors, artists and makers, seasonal brews, street food, sweets and treats – and other outdoor surprises.

Saturday, May 9th
11am-5pm
3rd Street (from Brown to Wildey)

Roxborough Spring Fest

Roxborough Spring Fest is a free event that goes from 11am to 4pm between Leverington Avenue and Fountain Street and will feature local artisans, food trucks and a car show with classic and custom vehicles.

May 9th

CineSpeak 

CinéSPEAK x Two Locals Brewing Company present Movie Mondays—a monthly gathering every 2nd Monday celebrating innovative Black filmmakers!

May 11 – 6pm – Sorry To Bother You @ Two Locals Brewing

From Keepers to Catalysts: Museums as Engines of Equitable Tourism

Hosted at the Fabric Workshop & Museum, an institution internationally recognized for artist-led experimentation and collaborative making, the setting reflects the conversation itself — museums as active spaces for innovation, dialogue, and public value.

May 20th – 5pm

Philadelphia Senior Expo Spring 2026

A fun and informative day at the Courtyard by Marriott Philadelphia City Avenue for the Philadelphia Senior Expo! Connect with local resources, learn about health and wellness, and discover new hobbies and activities.

May 21st – Courtyard Marriott, City Ave. – 10am 

Film Premiere – The Hired Man

Short crime film directed by Raw Leiba & William E. Heston, starring Raw Leiba.

May 23rd – 6p – 8p – Plays & Players Theater

Uranium Club, Mesh, and Nrg

This show is part of a free series “Live and Local”, in partnership with Delaware River Waterfront at Spruce Street Harbor, presented by 4333 Collective.

May 30th – 6pm – Spruce Street Harbor Park

Mini Hip Hop Museum Pop Up

Location revealed May 30th at 9:15am

May 30th & 31st 

Zine Swap 

Organized by Collide Zine and Stitch & Destroy – attendees are asked to bring zines and take Zines!

523 South 4th Street

May 31st

Liberty Bell Center – Always Free

It’s something to do.