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The best festivals to visit in Philadelphia during the month of May

Hosted by the Pennsylvania Academy of the Fine Arts community, PAFA Family Arts Day Spring Festival is held May 18 and celebrates the creativity of students and faculty.


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As summer approaches, the anticipation for festival season begins. Festivals remain one of Philadelphia’s most popular outdoor activities and there are plenty of opportunities to attend one this month. 

The Rittenhouse Row Spring Festival kicked the month off with more than 50,000 people in attendance last weekend. The festival offered live entertainment, food and beverage stands, and a variety of other local businesses promoting their brands.

If you didn’t get a chance to attend, the festivities will continue throughout the month. 

From the Festival of Fountains at Longwood Gardens to the New Hope PrideFest Celebration, there is an event to go to every weekend. Some of the most notable ones are listed below:

Variety Pack: An Alt Comedy Festival at The Drake 

May 1-3 & May 8-10, 2025

The Drake building, located on Rittenhouse Row, houses events for several organizations, including InterAct Theatre Company. The Variety Pack: An Alt Comedy Festival is a two-weekend-long event, hosted in the Louis Bluver Theatre inside the venue, where attendees can see a variety of unconventional alternative comedy performances. Offering a little bit of everything, this festival is a great opportunity to see stand-up, improv and sketch all in one event. 

Festival of Fountains at Longwood Gardens

May 9 - Sep. 28, 2025

Starting in May and continuing until late summer, Longwood Gardens begins its Festival of Fountains, where several fountains in Kennett Square will come to life this weekend. Performances include the Main Fountain Garden, with jets launching as high as 175 feet, and evening events where fireworks and light shows add to the experience. 

As another great way to appreciate the warmer weather, the festival also serves as an activity for Mother’s Day. 


The Festival of Fountains at Longwood Gardens is held all summer from May until September. 

African Liberation Day Health Festival & Uhuru Flea Market at Clark Park

May 17, 2025

The African Liberation Day Health Festival, held annually in Clark Park, was created by the African People’s Education & Defense Fund to recognize health disparities in Black communities. The event aims to educate participants through free health screenings, fitness activities, nutrition education and other health-related resources.

Co-siding with the event is One Africa! One Nation! Uhuru Flea Market, a cultural celebration with tables full of handmade art, food vendors, other community organizations, wellness practitioners, live music and other activities. The proceeds aim to support the economic self-determination of the African community of Philadelphia.

New Hope Celebrates PrideFest

May 17, 2025

New Hope Celebrates PrideFest is a festival inviting visitors from both sides of the Delaware River. As one of the first Pride events of the year, the festival has continued to grow in popularity over the last 20 years, bringing in a total of 15,000 since it began. 

The celebration lasts all week, but the pride parade & fair held on Saturday, with vendors, concerts and cocktail contests, are the highlight of the event.

HBCU Festival at The Mann Center

May 17, 2025 

Returning for its second year, the HBCU Festival, hosted at The Mann Center, brings a college fair, career fair, Black-owned business market, music event and spring festival to celebrate Historically Black Colleges and Universities. 

The event is free with advance registration and, as part of The Mann’s Summer Picnic Series, will only provide food and non-alcoholic beverages, with a BYO alternative.

Main Line Outdoor Beer & Wine Festival at Schauffele Plaza

May 17, 2025 

Across from the Ardmore Music Hall, the annual Main Line Outdoor Beer & Wine Festival will be held in two weeks, offering beer and wine from 22 breweries and wineries, including Spellbound Brewing, Broken Goblet Brewing and Love City Brewing.

In addition, food trucks & Ripplewood Whiskey and Craft will be available and Rags2Riches Animal Rescue will have open adoptions, along with live music and other attractions. 

South 9th Street Italian Market Festival

May 17-18, 2025

The South 9th Street Italian Market Festival is another top attraction for Philadelphia residents. The festival celebrates Italian and other diverse cultures through art, music and food, with everything from homemade sausages to cannolis.

Some less conventional attractions include the Procession of Saints parade, the John Marzano Half Ball Tournament and the greased-pole-climbing contest.

Attendees dancing to live music at the Italian Market Festival.

Chestnut Hill Home & Garden Festival

May 18, 2025

Offering the perfect opportunity to prepare for summer gardening and reorganizing, the Chestnut Hill Home & Garden Festival hosts 200 home, garden, vintage and artisanal vendors that line up across Germantown Avenue. If DIY doesn’t spark your interest, live music, dance and theatrical performances provide activities for the whole family. 

PAFA Family Arts Day Spring Festival at Lenfest Plaza

May 18, 2025 

PAFA Family Arts Day Spring Festival celebrates the creativity of students, faculty, artists, creators and the families that support them at the Pennsylvania Academy of the Fine Arts community.

The festival includes hands-on art-making stations, live music and performances and food and refreshments, to engage the community.  

Philadelphia Latino Arts & Film Festival

May 25 - July 6, 2025

Emerging Latino filmmakers put their work on display at the Philadelphia Latino Arts & Film Festival, showcasing feature films, shorts, animations, web series and documentaries. The schedule and venues of different films will be updated on PHLAFF’s website as the festival grows closer.  

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