May in Bennington: A Celebration of Spring, History, and Community

In Bennington, Vermont, May isn’t just a transition from mud season to sunshine, it’s a month that brings our community together through celebration, reflection, and the joy of the outdoors. Whether you’re here for a weekend or call Bennington home, these three signature events will have you falling in love with our little corner of Vermont all over again.

“May in Bennington reminds us that history isn’t just something we preserve—it’s something we live! It’s an awakening of the senses – the scent of blooming flowers, the sound of live music on our Main Streets, the taste of small-batch brews, and the sight of reenactors marching through history. As we celebrate Vermont’s 250th anniversary, we’re not only honoring the legacy of the Green Mountain Boys, we’re also showcasing the vibrant spirit of our community. From historic reenactments to homebrews and Main Street music, this month is a true reflection of what makes Southwestern Vermont so special – where the past and present come together to create an unforgettable experience.” — Matt Harrington, Executive Director, Southwestern Vermont Chamber of Commerce.

Can you find Ethan Allen? Expedition to Ticonderoga: A Journey Through History – May 3–4

Join the Expedition to Ticonderoga with a weekend commemorating the 250th anniversary of the Green Mountain Boys’ march to capture Fort Ticonderoga. This historic journey winds through the very landscapes where Ethan Allen and his band of patriots traveled in 1775—and you’re invited to join in. 

Saturday, May 3 begins with a Liberty Pole raising ceremony in Pownal at 10:30 am and continues with a Homebrew Festival in Bennington and historic sites such as the Old First Church and the Battle Monument in Old Bennington. In Shaftsbury, don’t miss the Jonas Galusha House where there will be a re-enactor encampment with musket demonstrations and drills throughout the day, kid activities, tours, liberty pole, informational tables, food truck, and a large muster or skirmish at 4 pm.

Sunday, May 4 continues the trek through Arlington, Sunderland, and Manchester, with events, musket salutes, tours, talks, and a ceremony at the Marsh Tavern, culminating in a symbolic powder horn passing in Pawlet. Want to go the extra mile? Join a group bike ride along the historic route or lace up your shoes for a fun run in Arlington.

Download a map of event locations, schedule, and more information at bennington250.org/expedition.

Get a stamp on your map or a selfie at at least one location and enter to win a basket of historical related prizes! Can YOU find Ethan Allen?

History isn’t something you only read about in Bennington, you live it.

Don’t miss the chance to explore more of Bennington’s historical landmarks and stories.

The 250th committee has more in store for you throughout the summer. Visit their website for more information.

Check out our guide to Bennington’s most cherished historic and cultural sites.

​​For the Adventure Seekers

Why not make it a day of moving through history? Join the Bike Hub for a group bike ride starting at 10 AM from the Liberty Pole ceremony in Pownal, continuing to the Jonas Galusha House event. A volunteer biker will carry a commemorative powder horn, just like the Green Mountain Boys of old. Or, lace up your running shoes for a fun run on Sunday afternoon through historic Arlington, starting at the junction of Route 313 and Route 7A, where you’ll pass through the town’s most historic sites.

Southern Vermont Homebrew Festival – May 3 

Brews! Bands! Bennington! Join us on Saturday, May 3rd for the annual Homebrew Festival in Bennington, Vermont and enjoy fresh home brewed beverages including Beer, Wine, Cider, Mead and more! You can expect a street fair atmosphere with live music; an interesting variety of delicious food from area food trucks; and of course, unlimited sampling of the best home brewed beverages in the region!

Shop, sample brew, and enjoy all the start of festival season in Vermont!

HIGHLIGHTS

• 30+ of the Best Regional HomeBrewers
• Unlimited Beverage sampling – 4oz samples
• Over 100 unique beverages you can ONLY sample at our festival
• Beverages include Beer, Cider, Wine, Mead
• Expect a variety of styles to include Sours, Pastry stouts, NEIPA’s, Porters, Pilsners, Fruited Mead, Belgians, Hard Ciders, White and Red Wine, and more!
• This is an OUTDOOR EVENT!

Third Thursdays Summer Series: Live Music and Hemmings Cruise-Ins, Starting May 13

Bennington’s popular concert series returns for 2025 with five Thursday evenings of live music, classic cars, and pure summer joy. Set right on Main Street, Thursday Night Live invites locals and visitors alike to gather with great tunes and good company.

This free event does not feature vendors or food trucks, and that’s by design. The event encourages attendees to support the fantastic local restaurants, boutiques, and bars that make Downtown Bennington special. From handcrafted gifts and Vermont-made goods to craft beer and artisan eats, your night on the town is also a night of supporting our neighbors.

“There’s something truly magical about May in Vermont, the way new life quietly awakens and brings with it a renewed sense of hope and excitement. Buds bloom, flowers stretch toward the sun, and beautiful downtown Bennington comes alive after a long, sleepy winter. At the Better Bennington Corporation, we’re embracing this vibrant energy as we dive into planning an unforgettable 2025 event season. It all begins with the return of Hemmings and Thursday Night Live on May 15, followed by the cherished 38th Annual Mayfest on May 24. We’re honored to bring entertainment and joy to those who live in, and love, this special place we call home.” — Jeanne Mintrone, Better Bennington Corporation Executive Director.

“Thursday Night Live is more than just a concert series, it’s about celebrating the local businesses that make Bennington unique. It’s community at its best.”
— Keith Carey, President of the Better Bennington Corporation (BBC) Board, and owner of the Gamers Grotto.

2025 Lineup:

• May 15 – Ransom Notes (Country, Soul, Rock & Roll)
• June 19 – MaxXander (Classic Rock)
• July 17 – Velvet Wave (Instrumental Surf Rock)
• August 14 – Roadhouse Rhythm and Blues Band
• September 11 – The Ray Gifford Band (Country)

Whether you’re grabbing a bite, browsing shops, or admiring vintage cars, Thursday Night Live is the perfect way to make the most of a summer evening in downtown Bennington.

Check out all the events happening in and around Bennington!

MayFest – Saturday, May 24

Now in its 38th year, MayFest returns to Downtown Bennington for a day filled with creativity, family fun, and the best of Vermont’s makers and artists. Main Street transforms into a bustling festival with over 130 vendors offering handcrafted goods, specialty foods, art, jewelry, and so much more.

With three stages of live music, a vibrant Kids’ Zone, and flavors from local food trucks and culinary artisans, MayFest is a signature kickoff to the summer season, and a joyful expression of Bennington’s creative, community-focused heart.

“Mayfest brings out the best in Bennington. It’s our chance to show off our creativity, our talent, and our community spirit…all in one place, while supporting the Downtown district.”
— Jeanne Mintrone, Better Bennington Corporation Executive Director

Bring the whole family, come hungry, shop local, and prepare to be inspired by the sights, sounds, and tastes of one of Southern Vermont’s favorite spring traditions.

Bennington’s Vibrant Arts Scene Blooms in May

May isn’t just about sunshine and celebrations, it’s also the start of an exciting season for the arts in Bennington. The Monument Arts & Cultural Center launches its summer lineup with gallery openings, a lively summer patio music series, and an array of creative camps for kids, from theater and music to hands-on fine arts workshops. Their upcoming gala, Let Us Entertain You, promises a night to remember, along with a full schedule of live performances throughout the season.

Just down the street, the Bennington Theater kicks off the month with a powerful production of 12 Angry Jurors, followed by psychic comedy with Peter Antoniou and modern country tunes from Nu-Blu.

Meanwhile, the Bennington Museum continues to delight with its beloved summer courtyard concert series and new exhibitions. The museum’s evolving approach emphasizes multisensory, interactive programming—especially for children—nurturing curiosity, lifelong learning, and a deeper connection to art, history, and community.

May in Bennington is a time of connection, celebration, and discovery.

From history buffs and music lovers to families and art enthusiasts, there’s something for everyone in Vermont’s Shires. And when the music fades or the vendors pack up, the adventures are far from over. Explore scenic rail trails, take a peaceful paddle down the Walloomsac River, or hike one of the many nearby Green Mountain trails bursting with spring color. Whether you’re wandering through downtown or heading for the hills, Bennington is your perfect launchpad for a season of outdoor exploration and small-town charm.

Check out our comprehensive guide for outdoor recreation.

Start planning your visit now at VermontBeginsHere.com.