Attending local events is more than just a break from binge-watching Netflix or doom-scrolling social media: it’s a chance to engage with the heartbeat of our city. Each festival, each gathering, is an opportunity to connect, uplift, and invest in the neighborhoods we care about, to known our community.
With cherry blossoms in full bloom and spring officially here, Philadelphia is buzzing with energy. Street festival season is kicking off in full swing, and our team at Real Estate Relief is excited to be out and about, soaking up the sun and celebrating the season with you.
Here are some of the events we’re most excited for this May—mark your calendars!
Dining Under the Stars in Media
Wednesdays, May 3 – Sept 27
Media’s charming State Street transforms into a pedestrian oasis every Wednesday night. Enjoy outdoor dining and evening strolls with live music, shopping, and some of the area’s best restaurants.
Girard Avenue Street Fest
May 6 (11AM – 5:30PM)
Hosted by Brewerytown, Sharswood, and Fairmount, this family-friendly fest features 90+ local vendors, games, food, live music, and a kid zone with bounce houses.
South Street Fest
May 6 (11AM – 7PM)
One of Philly’s biggest block parties! With food, music, dancing, and a festive Maypole, this event is fun for the whole family—don’t miss the beer garden at Brauhaus Schmitz!
Rittenhouse Row Spring Festival
May 6 (12PM – 5PM)
A must for foodies and fashion lovers, this upscale festival brings culinary demos, cocktails, and high-end shopping to the heart of Center City.
Spring Brewfest at Washington Crossing
May 6 (12:30PM – 4:30PM)
Sample 100+ brews from regional and national breweries. Complete with food trucks, live music, and a souvenir tasting glass—all supporting a great cause.
Strawberry Month Kickoff at Peddler’s Village
May 6–7 (11AM – 5PM)
Celebrate strawberries all weekend with food, drinks, and family fun. Can’t make it? Strawberry specials run all month long!
Chestnut Hill Home & Garden Festival
May 7 (11AM – 5PM)
For lovers of all things home and garden, this event showcases 150 vendors with decor, design, and handmade goods in Philly’s charming Garden District.
Kensington Derby & Arts Festival
May 13 (12PM – 6PM)
A creative celebration with a twist—human-powered derby vehicles race through an obstacle course while the neighborhood comes alive with art, music, and food.
5th Annual Festival of the Peony
May 18–28
Escape to Chadds Ford and wander fields of 30+ peony varieties. A beautiful experience for flower lovers and photographers alike.
South 9th Street Italian Market Festival
May 20–21
Philly’s iconic Italian Market comes alive with food, music, and cultural pride—don’t miss the legendary greased pole contest!
Roxborough Spring Fest
May 20 (12PM – 6PM)
Live performances, over 50 vendors, food trucks, and family-friendly activities make this an unforgettable neighborhood bash.
Fairmount Avenue Arts Crawl
May 21 (12PM – 4PM)
Local artists take over Fairmount for a day of creative celebration. Think painting, sculpture, music, and hands-on fun for all ages.
Northern Liberties Night Market
May 25 (5PM – 10PM)
The NoLibs corridor lights up with food, drinks, shopping, and performances in this beloved nighttime market.
Night Tours at Eastern State Penitentiary
May 25 – Sept 4
Explore one of Philly’s most famous landmarks by twilight. Enjoy exhibits, activities, and a beer garden on the penitentiary’s old baseball diamond.
Paddle Penn’s Landing
May 27 – Sept 4
Boat rentals return just in time for summer! Enjoy peaceful paddling during the day—or try a magical Starlit Paddle on select Saturday nights.
Come Say Hello!
We’ll be at several of these events, meeting our neighbors and celebrating the places we call home. Whether you’re looking for something fun to do, hoping to support small businesses, or simply want to see what Philly has to offer—these festivals are the perfect chance to get outside and feel the heartbeat of your city.
Let’s keep restoring our communities—one connection at a time. If you see the Real Estate Relief team out and about, come say hi!
