Bennington, Vermont: Celebrating Summer as an Appalachian Trail Community

July in Bennington means sunshine, outdoor adventure, and one special honor worth celebrating: Bennington is an official Appalachian Trail (AT) Community, recognized by the Appalachian Trail Conservancy for its commitment to supporting hikers and preserving the hiking experience. One of only 49 designated AT Communities along the 2,193-mile trail, Bennington is proud to welcome thru-hikers, section hikers, and local nature lovers with open arms and trail-friendly spirit.

Designated in June 2021, the honor reflects Bennington’s strong connection to outdoor recreation and its investment in conservation, access, and hospitality. This July, the town goes all in on celebrating that connection with TrailFest, a community gathering that’s part gear swap, part trail celebration, and all-around summer fun.

TrailFest: A Hiker-Friendly Celebration

Saturday, July 26, starting at 12:00 PM
Bennington Recreation Center, 655 Gage Street

Now in its fourth year, TrailFest is a free, family-friendly event that celebrates the Appalachian Trail, the hikers who journey along it, and the vibrant outdoor culture that defines Bennington.

New This Year

• Outdoor Gear Exchange – Bring or drop off gently used boots, tents, backpacks, maps, and more. You can donate in advance by emailing [email protected]. All gear is offered freely, take what you need, give what you can.
• Trail of Fortune Game – Spin to win outdoor-themed prizes and giveaways.
• Live Music & Food – Enjoy fresh BBQ from The Abbey Group and a pop-up by Grateful Hearts, offering farm-fresh and local eats.

Meet Local Organizations

From the Green Mountain Club, Bennington Section to Bike Hub, Gardner Health & Fitness, Wicked Way Station, Holy Hikers, Green Mountain National Forest, and Meals on Wheels, this year’s event includes trail-friendly groups committed to wellness, education, and sustainable outdoor fun.

Many downtown Bennington businesses are also showing their support, offering discounts and services for hikers and visitors. Look for AT Community stickers at Harvest Brewing, Bennington Community Market, Bennington Pizza House, Catamount Motel, Henry’s Market, and other walkable local destinations.

“We want hikers and locals to connect,” says Camille Kauffman, co-chair of the Bennington AT Community Committee. “Whether it’s at a BBQ table or over gear stories, TrailFest is about building community and getting people excited about what’s in their own backyard.”

Kauffman moved to Bennington in 2020 and quickly became involved in promoting outdoor recreation. “I love that we have access to clean, swimmable fresh water and a national forest practically in our backyard,” she said. “You can go from work to the woods in five minutes.”

Her personal recommendations include:

• BATS Trails for casual hikes like Everett Cave and the Halloween Tree Trail
• Harmon Hill for great views with a challenging climb
• Taconic Crest Trail, starting at Petersburg Pass in Massachusetts and heading north past the Snow Hole into Pownal
• Little Pond Trail in Woodford
• Styles Peak and Baker Peak, accessible from the Long Trail in Peru and Danby

TrailFest highlights Bennington’s recreational gems while welcoming all who love the outdoors. Whether you’re a long-distance hiker, weekend adventurer, or simply outdoor-curious, it’s a chance to connect with others who share a passion for the trail.

July 26: A Day Full of Events

• 12:00 PM – TrailFest at the Bennington Recreation Center
• 1:30–4:30 PM – ArtsFest on the Downtown Bennington Riverwalk; free pop-up workshops, performances, community painting projects and more. View the new sculptures and learn about Phase 2 of the Barn Quilt Boards Trail in Bennington.
• 5:00–7:00 PM – Alex Torres Latin Concert and Dance Workshop at Thomson Stage in Merchants Park, produced by Vermont Arts Exchange in partnership with the Better Bennington Corporation.
• 7:30 PM – Live Outdoor Music at Tina’s Cantina (Madison Brewing Co.)

With so many events within walking distance, it’s the perfect day to explore downtown Bennington on foot.

Fourth of July in Bennington: A Freedom Journey

This year’s Fourth of July celebrations in Bennington offer a unique historical and patriotic experience, with a series of programs collectively titled the Freedom Journey. The day’s activities invite residents and visitors to travel between several sites of local and national significance, beginning at the Bennington Battlefield and concluding with fireworks at Willow Park.

“As we celebrate the Fourth of July and the founding ideals of our nation, there’s no better place to reflect on American independence than Bennington – Vermont’s first town. From its Revolutionary War monument to its neighborly charm, Bennington offers that timeless small-town feeling Don Henley sang about – where freedom isn’t just a historical fact, but a way of life. Whether you’re visiting or lucky enough to call it home, Bennington reminds us that the spirit of America still lives on in places like this,” said Matt Harrington, Executive Director of the Southwestern Vermont Chamber of Commerce.

All events are free and open to the public. Driving directions are available at the Bennington Battle Monument, and participants can enjoy a scenic route that crosses three covered bridges. Motorcyclists are especially encouraged to participate.

Schedule of Events – Thursday, July 4:

• 10:30 AM – Bennington Battlefield: Interpretive Programs Manager David Pitlyk introduces reenactor Sean Considine as British Gen. John Burgoyne. A reading of the general’s proclamation and a ceremonial toast to independence follow.
• 11:30 AM – Bennington Battle Monument: Program begins, including a reading of the Women’s Declaration of Rights by Phyllis Chapman.
• 12:00 PM – Bennington Battle Monument: Mike Chapman reads the Declaration of Independence.
• 1:00 PM – Bennington Town Offices: Bell Ringing Ceremony and musket salute. The bell, once housed on the USS Bennington, will be rung 13 times by members of the Bennington Rotary Club, representing the original 13 states. A 14th ringer is chosen each year to honor Vermont.

This year, the 14th bell ringer will be the Vermont Veterans’ Home, recognized for its service and commitment to the community. After the ceremony, members of the public are invited to ring the bell as well.

Evening Festivities at Willow Park:

• 5:00 PM – Food and craft vendors open
• 5:00–6:00 PM – Performance by the Crossover Cloggers
  
• 6:00–8:30 PM – Live music
• 9:30 PM (dusk) – Fireworks Display. Rain date: Friday, July 5

Fireworks are sponsored by Market 32 / Price Chopper, Casella Waste Management, MSK Engineering, and the Bennington Banner.

Explore Bennington’s Summer Outdoors

Beyond July’s events, Bennington offers expansive outdoor access for hiking, biking, paddling, and exploring. The Bennington Area Trail System (BATS), with over 17 miles of trails, is popular for mountain biking and trail running. Locally loved trails like Zaphod’s Run, Halloween Tree Trail, and Everett Cave are all accessible from town.

For hiking, nearby routes like the Harmon Hill Trail and Bald Mountain Trail offer scenic overlooks with moderately challenging climbs. The Long Trail and Appalachian Trail both cross through the region, making Bennington a hub for day hikers and long-distance trekkers alike.

Water access includes Lake Paran in North Bennington, Lake Shaftsbury State Park, and Woodford State Park, as well as spots along the Walloomsac River and Roaring Branch for fishing or wading. Cyclists can enjoy trails in Willow Park, the Downtown Riverwalk, and the newly reopened Bennington Rail Trail.

Volunteer and advocacy organizations such as BATS, the Green Mountain Club, and the Fund for North Bennington help preserve these natural spaces through community engagement and environmental education.

As BATS co-founder Jim Sullivan puts it, “You don’t have to go far to feel like you’ve escaped. These trails are right out your back door, and they offer something different every season.”

Plan Your Visit

Bennington is located about an hour from Albany, New York, and less than three hours from Boston. It’s easily accessible for weekend getaways, summer festivals, and outdoor excursions. Visit vermontbeginshere.com for updated schedules, trail information, lodging, and dining options.

For more information on the Appalachian Trail Community program, visit appalachiantrail.org.