May 2025 Events in Williamsburg, VA – Music, Markets, & More!

Spring is in full bloom, and Williamsburg is buzzing with exciting events for every kind of local and visitor alike. Whether you’re craving live music, local beer, fresh food, or creative art, there’s something on the calendar this May you won’t want to miss. Here's a roundup of the best happenings around town:

🍻 Williamsburg Craft Beer Festival

📅 Saturday, May 3
Raise your glass for a cause! The 10th annual Williamsburg Craft Beer Festival is back and better than ever, serving up an afternoon of craft brews, live music, and local eats. Even better—100% of proceeds benefit area nonprofits including Colonial CASA, Literacy for Life, Thread Local Charities, and Williamsburg Area Meals on Wheels. Sip and support a great cause!

🎶 New Town Tunes

📅 Wednesdays, May 7–June 11 | Sullivan Square behind Legacy Hall
Wind down your Wednesdays with lawn chairs, picnic baskets, and live local music at this free family-friendly concert series. Hosted by New Town Commercial Association and CultureFix, New Town Tunes is the perfect way to midweek unwind with brews, bites, and community vibes. Pets welcome!

🌸 2nd Sundays – Mother's Day Edition

📅 Sunday, May 11 | Downtown Williamsburg
Celebrating its 16th season, 2nd Sundays Art & Music Festival fills six blocks of downtown with handmade art, crafts, live music, local food trucks, and an all-around vibrant atmosphere. It's the perfect way to treat mom to a relaxing day of shopping small and supporting local artisans. Check the artisan lineup the week before at 2ndsundayswilliamsburg.com.

🌿 Native Plant Sale

📅 May dates vary | Visit VNPS.org
Looking to grow a greener garden? This native plant sale features perennials, shrubs, and trees perfect for Virginia landscapes. It’s a great opportunity to learn from native plant enthusiasts and discover how to create a more eco-friendly garden. Bonus: volunteer opportunities are available!

🍓 Williamsburg Farmers Market

📅 Every Saturday | 300 Block of Duke of Gloucester Street
Your weekend plans just got better. The Williamsburg Farmers Market runs through December, featuring everything from fresh produce and baked goods to handmade soaps and live music. Whether you're a regular or a first-timer, you'll love the community spirit and seasonal finds each Saturday.

🍷🏃 Busch Gardens Food & Wine Festival 5K

📅 Sunday, May 4 | Busch Gardens Williamsburg
Lace up your sneakers and get ready to race through the world’s most beautiful theme park! The inaugural Food & Wine Festival 5K is a feast for the senses, offering a scenic course through the park’s European villages and a tasty reward at the finish line. Run, sip, repeat!

🎤 Music in Midtown – Revelation

📅 Thursday, May 8 | Midtown Row Village Green
Revelation is bringing the energy to kick off the 2025 Music in Midtown series! Pack a picnic and gather at Midtown Row for a free outdoor concert full of great music and good vibes. This series runs every 2nd Thursday through September, and yes—leashed pets are welcome!

🏓 4th Annual Community Pickleball Challenge

📅 May date TBA | Benefiting The Arc of Greater Williamsburg
Game on! This two-part pickleball challenge is as fun as it is meaningful. Your participation supports local programs for adults with intellectual and developmental disabilities through The Arc of Greater Williamsburg. It’s a great way to stay active and give back!

🎤 Virginia Team Poetry Slam Championship

📅 May date TBA
Prepare to be inspired as six Virginia slam teams compete for the state title! This high-energy event celebrates the power of spoken word while raising funds for teams traveling to the Southern Fried Poetry Slam in Knoxville. Come cheer them on and experience poetry like never before!

✨ Whether you’re sipping beer, dancing to live music, or shopping local at the market, May is full of memorable moments in Williamsburg. Which event are you most excited about? 👇