15 Must-Attend Spring Events in Philadelphia and the Main Line (2025 Guide)
Spring’s here in full swing, and if you’re anything like me, you’re ready to make the most of it. After months of chilly mornings and juggling everything indoors, there’s just something about being outside - whether it’s coaching baseball, catching a local event, or just soaking in the sunshine - that resets the energy. Around here, the calendar starts filling up fast with festivals, street fairs, and all kinds of local happenings, so I wanted to pull together a list of spring events happening in Philly and along the Main Line that are worth checking out.
Whether you're looking for a fun day with the kids, a good excuse to grab lunch from a food truck, or just want to explore a new neighborhood, there are some great options coming up. These are perfect if you’re asking, “What are some things to do in Philadelphia this spring?” or looking for Main Line events to enjoy over the weekend. Here’s a roundup of what’s happening after May 5, 2025:
Philadelphia Spring Events & Festivals
May 10, 2025 | Roxborough
Enjoy local music, art, food, and brews at this annual celebration. The car show features classic and custom cars, making it a treat for enthusiasts and families alike.
May 18, 2025 | Chestnut Hill
Stroll along Germantown Avenue and explore over 300 vendors offering home and garden goods, crafts, and more. Live music and family activities add to the festive atmosphere.
May 18, 2025 | Center City
Join the Pennsylvania Academy of the Fine Arts for a day of art-making, live music, and delicious food. It's a great opportunity for families to engage with the arts.
May 16–17, 2025 | Schuylkill River
Witness the largest high school rowing competition in the world. The regatta features teams from across the country competing on the scenic Schuylkill River.
May 31 – June 1, 2025 | Fairmount Park
Experience a weekend of music, culture, and community curated by The Roots. The lineup includes renowned artists and emerging talent across various genres.
May 23 – June 1, 2025 | FringeArts, Old City
Discover innovative performances that blend acrobatics, dance, and theater. This festival showcases the talents of contemporary circus artists from around the world.
May 17–18, 2025 | Italian Market, South Philly
Celebrate Italian culture with food, music, and the famous grease pole contest. The festival spans several blocks and features vendors offering a variety of goods.
May 17, 2025 | 2300 Arena, South Philly
Catch the excitement of professional wrestling as top teams compete in this prestigious tournament. The event promises high-energy matches and entertainment.
Main Line Spring Events
May 21 – June 1, 2025 | Devon, PA
Attend the oldest and largest outdoor multi-breed horse competition in the U.S. The event includes exhibitions, shopping, food, and family-friendly activities.
May 17, 2025 | Schauffele Plaza, Ardmore, PA
Sample a variety of beers and wines while enjoying live music and food trucks. The festival offers a relaxed atmosphere for adults to unwind.
Through May 19, 2025 | Chester Springs, PA
Explore works from over 200 artists in a range of mediums. The show is set in a historic village, providing a charming backdrop for art enthusiasts.
May 2–25, 2025 | Media, PA
Enjoy a live performance of the classic musical "Grease." The production features catchy tunes and energetic dance numbers that will have you tapping your feet.
May 10–11, 2025 | Kennett Square, PA
Celebrate Mother's Day with a visit to the stunning Longwood Gardens. The weekend includes special fountain performances and beautiful floral displays.
Additional Events
May 10–11, 2025 | Cherry Street Pier, Philadelphia
Shop handmade goods from over 100 artists at this open-air market. The event also features live music and food vendors along the waterfront.
May 17, 2025 | Cherry Street Pier, Philadelphia
Learn about sustainable living through workshops, vendor exhibits, and interactive activities. The fair is a great opportunity to engage with local environmental initiatives.
So whether you’re staying local or making a trip into the city, there’s no shortage of things to do this spring. These events are a great way to support small businesses, discover something new, and just enjoy the season with friends or family. And if you're headed to any of these - especially the ones near Ardmore - reach out! I'd love to hear what you think.
Here’s to warmer weather, good food, and a packed calendar (in the best way).
— Justin
