August might be the best month to experience everything Bennington has to offer.

The trails are green, the rivers are flowing, outdoor dining is in full swing, and the community calendar is filled with festivals, concerts, historic celebrations, and traditions that bring visitors and locals together.

From exploring the region’s outdoor recreation to enjoying live music downtown, discovering local businesses, visiting museums and galleries, or celebrating Vermont history during Bennington Battle Day Weekend, August offers countless reasons to plan a visit, and maybe even plan more than one trip.

This month also marks the beginning of preparations for one of Southern Vermont’s signature celebrations: Garlic Town, USA, returning Labor Day Weekend for its 31st annual festival. With more than 130 vendors, live entertainment, chef demonstrations, and plenty of garlic-inspired food, August is the perfect time to start planning your end-of-summer getaway.

Bennington Battle Day Weekend

Celebrating Vermont History & Community

Every August, Bennington comes together to celebrate one of Vermont’s most unique holidays: Bennington Battle Day.

The holiday commemorates the 249th anniversary of the 1777 Battle of Bennington, a pivotal Revolutionary War victory that helped shape the future of Vermont and the United States.

The weekend blends history, community traditions, family activities, and downtown celebrations.

Bennington Battle Day Weekend Schedule

Saturday, August 15

The Annual 5K race sponsored by the Friends of the Bennington Battle Monument.

Shirt pickup at 7:30 AM. Race and fun run for kids starts at 8:30 AM. There will be Raffles and prizes. Register online.

Kids Day — Vermont Veterans Home

10 a.m.–1 p.m.
Parking available behind the Veterans Home or on Park Street.

A family-friendly celebration welcoming children and families for activities and community fun.

Moodus Drum and Fife Presentations

12 p.m. Bennington Battle Monument – Monument Circle.

4 sets of 20 minutes with 10 minute breaks. A free open air concert with the Moodus Drum and Fife takes place on the lawn. A 135 year-old tradition, the Corp played at the dedication of the Monument in August of 1891, same drums, and same style. Bring a chair or blanket and sit back and enjoy an afternoon of 18th century music.

USS Bennington Memorial Service
Town Offices — 205 South Street
Noon–1 p.m.

A ceremony honoring the USS Bennington and those connected to its history.

Food Truck Festival — Downtown Bennington
11 a.m.–7 p.m.

Enjoy local food trucks, live entertainment, and a full day of activity downtown.

Sunday, August 16

Bennington Battle Day Parade

Downtown Bennington
12:30 p.m. step-off
(Parade participant lineup begins at 10 a.m.)

One of Bennington’s most beloved traditions, bringing together community organizations, performers, and visitors from throughout the region.

Saturday and Sunday

Bennington Battle Monument –  10 am to 5 pm Saturday, 10 am to noon Sunday. Battle of Bennington encampment with re-enactors and cannons and musket demonstrations. WARNING: for neighbors, people with small children or dogs, musket and cannon fire entails loud noises.

Explore more of Bennington’s history, museums, monuments, and Revolutionary War destinations here.

Community Events & Summer Traditions

August Brings Everyone Together

August is also a month filled with community celebrations, fundraisers, and local traditions.

The Bennington Fire Department hosts several annual events throughout the month, offering great food, family activities, and opportunities to support one of Bennington’s most dedicated organizations.

Bennington Fire Department Events

Basket Bingo
Saturday, August 8
Elks Club — 125 Washington Avenue
Doors open at 5 p.m.
$15 entrance fee
Tickets available at the Bennington Fire House and at the door.

Fireman’s Lunch
Friday, August 14
11 a.m.–2 p.m.
Bennington Firehouse — 130 River Street

Open to the public, featuring sausage with peppers and onions, burgers, hot dogs, and fries.

Chicken Barbecue
Friday, August 14
4–6 p.m.
Bennington Firehouse — 130 River Street

Dine-in or take-out.

Vegas Night
Friday, August 14
6–9 p.m.
Bennington Firehouse — 130 River Street

Big Truck Night
Friday, August 14
5–9 p.m.
Across from the Firehouse — 130 River Street

A favorite family event featuring large vehicles and community fun.

See more community events happening throughout Bennington here.

Downtown Bennington

Classic Cars, Live Music & Summer Nights

Downtown Bennington continues its summer tradition of bringing people together through cars, music, and local businesses.

On Thursday, August 13, Hemmings Cruise-In returns in partnership with Hemmings Motor News and Better Bennington Corporation.

From 5–8 p.m., Main Street transforms into a showcase of classic, vintage, collectible, and specialty vehicles, bringing together passionate car owners and visitors for one of downtown’s most unique summer evenings.

The evening’s live entertainment features Velvet Wave, Bennington’s own surf rock band.

Discover more downtown events, restaurants, shopping, and experiences here.

Outdoor Recreation

Peak Summer Adventures

August is one of the best months to enjoy the outdoors in Bennington.

Local trails, parks, rivers, and public spaces are at their summer best. Whether you enjoy hiking, biking, paddling, fishing, or simply relaxing outside, there are plenty of ways to experience the natural beauty surrounding Bennington.

The Bennington Skatepark continues welcoming skaters, BMX riders, and scooter enthusiasts from throughout Vermont, New York, and Massachusetts, while Willow Park remains a gathering place for sports, recreation, and family activities.

August is also a great time to explore the region’s scenic trails and outdoor destinations before the arrival of fall.

Explore Bennington’s full outdoor recreation guide here.

Plan Your Labor Day Weekend

Garlic Town, USA Returns

While August is full of events, the community is already preparing for one of Bennington’s biggest celebrations of the year.

Garlic Town, USA returns Labor Day Weekend for its 31st annual festival.

Visitors can expect more than 130 vendors, live entertainment, chef demonstrations, family activities, artisan goods, and some of the most creative garlic-inspired food in the region.

Make your plans early, Labor Day Weekend is one of the best times to visit Bennington.

Learn more about Garlic Town, USA and plan your visit here.

Whether you’re coming for a single event or planning a long weekend, August showcases nearly everything that makes Bennington special, history, outdoor adventure, arts, local businesses, festivals, and a community that loves welcoming visitors.

Follow Vermont Begins Here on Facebook and Instagram for weekly event updates, subscribe to our newsletter for seasonal itineraries, and explore even more ways to experience Bennington at VermontBeginsHere.com.