May Events Around Philadelphia You Won’t Want to Miss

May is one of the best times to get out and explore the Philadelphia region. With warmer weather, blooming gardens, outdoor festivals, sporting events, and beloved local traditions, the month is packed with things to do across the city and surrounding suburbs.

Whether you’re looking for a family-friendly weekend outing, a lively neighborhood festival, or a signature regional event, here are some highlights to add to your May calendar.

Chestnut Hill Home and Garden Festival

May 3 | 11 AM – 5 PM | Chestnut Hill

The Chestnut Hill Home and Garden Festival is a favorite spring tradition along Germantown Avenue. This vibrant outdoor marketplace transforms the neighborhood into a lively destination filled with more than 300 vendors offering plants, garden décor, handcrafted furniture, art, artisan goods, and home design inspiration.

Guests can also enjoy live music, local food vendors, and a Makers Village where artisans demonstrate their crafts in real time. It’s the perfect event for anyone who loves gardening, home design, shopping local, or simply spending a beautiful spring day outdoors.

Pride Parade and Vendor Fair

May 9–17 | New Hope

New Hope celebrates PrideFest with a week of events focused on inclusivity, community, and celebration. The festivities include a signature Pride Parade crossing the Delaware River between New Hope and Lambertville, along with a vendor fair, live entertainment, parties, and community programming.

The parade and fair are the centerpiece of the celebration, highlighting local organizations, performers, vendors, and community members. It’s a colorful, energetic event that brings people together through advocacy, art, entertainment, and connection.

2026 PGA Championship at Aronimink Golf Club

May 11–17 | Delaware County’s Aronimink Golf Club

The 2026 PGA Championship is coming to the Philadelphia region, bringing one of golf’s biggest events to Aronimink Golf Club. This major international tournament will draw more than 150 top players and an estimated 200,000 spectators throughout the week.

In addition to championship-level golf, the event will feature merchandise shops, food and beverage areas, and hospitality spaces. For golf fans and sports enthusiasts, this is one of the standout events of the season.

South 9th Street Italian Market Festival

May 16–17 | South Philadelphia

The South 9th Street Italian Market Festival is one of Philadelphia’s largest and most beloved street festivals. Held along several blocks of the historic Italian Market, this two-day event brings together food, culture, music, and neighborhood tradition.

Visitors can enjoy food vendors, live music, artisan goods, local businesses, and classic festival moments like the famous greased pole climb. With its lively atmosphere and deep community roots, the Italian Market Festival is a must-visit spring event in South Philadelphia.

Devon Horse Show

May 20–31 | Devon Country Fair

The Devon Horse Show & Country Fair is one of the most historic and prestigious equestrian events in the country. Dating back to 1896, this long-running tradition attracts top riders, trainers, and spectators from around the world.

Beyond the competitions, the event offers boutique shopping, dining, family-friendly entertainment, and carnival rides. It’s both a premier sporting event and a classic Main Line tradition, with proceeds supporting Bryn Mawr Hospital.

Make the Most of May

From blooming gardens and neighborhood festivals to championship golf and historic equestrian events, May offers something for everyone in and around Philadelphia. Whether you’re planning a weekend outing, entertaining guests, or simply looking for a new local experience, these events are a great way to enjoy the season.

Spring is in full swing — and Philadelphia is ready to celebrate.