The Best Spring Events in Philadelphia: May Festivals, Street Fairs, and Local Fun

Living in Philadelphia means never having to wonder what to do with your weekend. When the weather warms up, the city bursts into bloom—not just with flowers, but with festivals, block parties, craft markets, and beer gardens that spill out onto every sidewalk and plaza. From iconic traditions like the Broad Street Run to quirky newcomers like Eraserhood Fest, May in Philly is a nonstop celebration of what makes this city vibrant, creative, and just a little weird (in the best way). Whether you’re strolling under stars in Media, shopping indie finds at Cherry Street Pier, or cheering on racing goats in Pottstown, these events are a reminder that in Philly, the streets don’t just connect neighborhoods—they connect people, culture, and good times. Let’s get into it.

Chic & Street: Rittenhouse Row Spring Festival

One of the city's most stylish events, the Rittenhouse Row Spring Festival brings a touch of glam to the city streets. Walnut Street becomes a hub for upscale eats, fashion shows, cocktail samples, art activations and live music. With over 50,000 attendees, it’s the ultimate spring stroll through one of Philly’s poshest neighborhoods. Free to enter, with plenty of splurge-worthy stops.

📍Walnut Street from 15th–19th & 18th Street from Locust to Sansom, Philadelphia, PA

🗓️ May 3, 2025 | Noon-5 p.m.

Beats & Brews: South Street Live! & Maifest

South Street’s biggest bash is back, now rebranded as South Street Live! and packed with energy. This all-day block party features food trucks, local artists, a Vinyl Block Party, Free Comic Book Day giveaways, and live music. Don’t miss Maifest by Brauhaus Schmitz, where you’ll find traditional German beer, food and Maypole dancing. A perfect mashup of Philly flavor and festivity.

📍South Street between 2nd & 8th Streets, Philadelphia, PA

🗓️ May 3, 2025 | Noon-8 p.m.

City Sprint: Independence Blue Cross Broad Street Run

One of Philly’s proudest race day traditions, the Broad Street Run brings over 35,000 runners down 10 miles of cheering crowds, live music, and city spirit. From North Philly to The Navy Yard, the course runs straight through the heart of the city. Whether you’re running or spectating, the energy is electric. Pro tip: be there by 6:30 a.m. for the best views.

📍Broad Street from Fisher Avenue to The Navy Yard, Philadelphia, PA

🗓️ May 4, 2025 | 7 a.m.

Bloom & Build: Chestnut Hill Home + Garden Festival

Chestnut Hill blossoms with creativity at the Home + Garden Festival, featuring 200+ vendors selling everything from vintage furniture to rare plants and handmade goods. Explore demos in the Makers Village, let kids roam the activity zone, and grab a bite from a local food truck. With live music and spring vibes in the air, it’s the perfect Sunday outing.

📍Germantown Avenue between Rex Avenue & Willow Grove Avenue, Philadelphia, PA

🗓️ May 4, 2025 | 11 a.m. - 5 p.m.

Alfresco Evenings: Dining Under the Stars in Media

Every Wednesday from May to September, Media transforms into an open-air culinary escape during Dining Under the Stars. State Street closes to traffic, making way for outdoor dining, live music, and sidewalk shopping from local restaurants and boutiques. Enjoy chef specials, seasonal cocktails, and laid-back strolls under twinkling lights. A perfect midweek outing with friends or a date.

📍State Street between Jackson Street and Orange Street, Media, PA

🗓️ May 7 – September 24, 2025 (Wednesdays only)

Romance & Technique: La Sylphide & Études by Philadelphia Ballet

This May, the Philadelphia Ballet presents a mesmerizing double bill at the Academy of Music. La Sylphide tells a timeless Romantic story of enchantment and longing, while Études displays the raw technique and beauty of classical ballet. From magical forests to pointe perfection, this performance spans the emotional and technical range of dance. Ideal for ballet lovers and newcomers alike.

📍Academy of Music, 240 S. Broad Street, Philadelphia, PA

🗓️ May 8-11, 2025

Summer Magic: Festival of Fountains at Longwood Gardens

Water meets artistry at Longwood Gardens’ Festival of Fountains, running all summer long. Catch daily Main Fountain Garden performances with jets soaring up to 175 feet, plus dazzling nighttime illuminated shows. Explore the new Conservatory Overlook and take in choreographed displays in the historic Open Air Theatre. A cool and refreshing experience for all ages.

📍Longwood Gardens, 1001 Longwood Road, Kennett Square, PA

🗓️ May 9 - September 28, 2025

Handmade Mastery: Rittenhouse Square Spring Fine Craft Show

Celebrate craftsmanship at the Rittenhouse Square Spring Fine Craft Show, featuring over 140 artisans. Browse ceramics, jewelry, wearable fiber, photography, and more—all handmade by talented creators. This free, rain-or-shine event offers a rare chance to meet makers and shop directly in the heart of the city. A must for lovers of functional art.

📍Rittenhouse Square, 1800 Walnut Street, Philadelphia, PA

🗓️ May 9-11, 2025

Community Jam: Roxborough Spring Fest

Ridge Avenue comes alive for the annual Roxborough Spring Fest, packed with live music, local food trucks, art, and family fun. With three stages of performances, a dedicated Kids Zone, and a student art showcase, there’s something for everyone. Don’t miss the craft beer stands and street eats from local favorites like New Ridge Brewing Co. Celebrate local pride in one big block party.

📍Ridge Avenue between Lyceum Avenue and Leverington Avenue, Philadelphia, PA

🗓️ May 10, 2025 | 11 a.m. - 6 p.m.

Waterfront Finds: Spring Art Star Craft Bazaar

Cherry Street Pier transforms into an indie marketplace during the Spring Art Star Craft Bazaar. With over 80 vendors selling handmade goods—from ceramics to home décor—you’ll find plenty of creative treasures. Enjoy food, drinks, free tote bags, and DIY activities while shopping. Free entry, pet-friendly, and full of Philly charm.

📍Cherry Street Pier, 121 N. Christopher Columbus Boulevard, Philadelphia, PA

🗓️ May 10-11, 2025

A Soulful Tribute: Mother’s Day Gospel Celebration

Celebrate the powerful women in your life at the Mother’s Day Gospel Celebration at The Liacouras Center. The all-star lineup features Donnie McClurkin, Kurt Carr, Hezekiah Walker and more, hosted by comedian Jonathan Slocumb. Add a pre-show chef-curated supper club dinner for the full experience. A day of love, music, and praise.

📍The Liacouras Center, 1776 N. Broad Street, Philadelphia, PA

🗓️ May 11, 2025 | 4 p.m.

Geek Out in Style: Fan Expo Philadelphia

Fandoms unite! Fan Expo returns with celeb guests like William Shatner, Jodie Whittaker, and Giancarlo Esposito, alongside hundreds of artists, vendors, and immersive experiences. Panels, cosplay contests, screenings, and fan meetups take over the Pennsylvania Convention Center. Whether you're into sci-fi, comics, anime or horror, there's a place for you here.

📍Pennsylvania Convention Center, 1101 Arch Street, Philadelphia, PA

🗓️ May 16-18, 2025

Street Vibes: Girard Avenue Street Fest in Brewerytown

Celebrate community at the Girard Avenue Street Fest, a vibrant day filled with food, music, vendors and family fun. With 100+ local businesses, a kids zone, and live bands all day, the event showcases the best of Brewerytown, Fairmount, and surrounding neighborhoods. Bring the crew, grab a bite, and dance in the street!

📍 West Girard Avenue between College Avenue and 29th Street, Philadelphia, PA

🗓️ May 17, 2025 | 11 a.m. - 5:30 p.m.

Mangia! South 9th Street Italian Market Festival

Philly’s oldest curb market hosts a weekend of unbeatable flavor and fun at the Italian Market Festival. Stroll seven festive blocks with live music, parades, cultural games, and the ever-entertaining greased pole contest. Dig into homemade sausage, pasta, cannoli, and more from beloved neighborhood vendors. A South Philly tradition worth the wait.

📍 South 9th Street Italian Market, Philadelphia, PA

🗓️ May 17-18, 2025

Art for All: PAFA Family Arts Day Spring Festival

Gather the family for an afternoon of hands-on creativity at PAFA Family Arts Day on Lenfest Plaza. Enjoy live performances, music, food and interactive art-making in the shadow of the famous Paint Torch sculpture. It’s a colorful way to celebrate spring, community, and artistic expression. Free and open to the public.

📍Lenfest Plaza, 1537 Cherry Street, Philadelphia, PA

🗓️ May 18, 2025 | 1-4 p.m.

Cheers to the City: Philly Beer Week

Raise your glass! Philly Beer Week returns for 10 days of tastings, pub crawls, brewery events and beer-fueled fun across the city. With local legends and visiting breweries pouring their best, there’s something new on tap every day. Follow the official calendar for events and surprise releases. Let the pours begin!

📍Various locations throughout Philadelphia, PA

🗓️ May 30 - June 8, 2025

Sounds of the City: The Roots Picnic 2025

The Roots Picnic is back and bigger than ever at The Mann, with a lineup including D’Angelo, Meek Mill, and Lenny Kravitz. Join thousands of fans for a weekend of hip-hop, R&B, soul, and community vibes curated by Philly’s own The Roots. With food, culture and live music all weekend long, this is the summer kickoff event.

📍The Mann Center, 5201 Parkside Avenue, Philadelphia, PA

🗓️ May 31 - June 1, 2025