If Manchester is Vermont’s postcard-perfect village, Bennington is its storybook of history, heritage, and hidden gems.
Nestled in the state’s southwestern corner, this small town becomes an autumn paradise in October — blazing foliage, crisp mountain air, pumpkin patches, historic covered bridges, and a charm that feels both timeless and welcoming.
Whether you’re a history buff, a hiker chasing fall views, or simply in it for the cider doughnuts, Bennington in October delivers.
Here’s your guide to the 22 best things to do in Bennington this fall, from cultural icons to outdoor escapes and foodie must-stops.
Read More: 20+ Best Places to Visit in Vermont in October
Historic & Cultural Landmarks
Bennington Battle Monument
Standing tall at 306 feet, the Bennington Battle Monument is Vermont’s tallest manmade structure and a symbol of the Revolutionary War.
In October, the views from the observation deck stretch across fiery treetops into Massachusetts and New York.
Pro Tip: Visit in the morning to beat crowds and catch mist lifting off the valley for dreamy photos.
Old First Congregational Church & Robert Frost’s Grave
This 1805 white clapboard church is one of New England’s most photographed landmarks.
Wander into the cemetery and you’ll find the resting place of poet Robert Frost, with his famous epitaph: “I had a lover’s quarrel with the world.”
With maple leaves carpeting the ground, it feels like stepping into poetry itself.
Bennington Museum
The museum is small-town Vermont with big surprises.
It houses the largest public collection of Grandma Moses paintings, Revolutionary War artifacts, and fascinating exhibits about local history.
The grounds outside are just as charming in October, with sculptures framed by golden foliage.
Park-McCullough Historic House (North Bennington)
This Victorian mansion tells the story of Vermont’s Gilded Age, with more than 30 furnished rooms preserved from the 1800s.
Walking through feels like traveling back in time, and the leafy gardens add a romantic fall backdrop.
Robert Frost Stone House Museum (Shaftsbury)
Step inside the farmhouse where Frost lived and wrote some of his most famous works.
The house, stone-walled and rustic, is especially atmospheric in autumn.
The surrounding trails feel like an extension of his poetry.
Covered Bridges & Scenic Charm
Silk Road Covered Bridge
Bennington is famous for its covered bridges, and the Silk Road Bridge is the most iconic.
Draped in orange and red leaves in October, it looks like a scene pulled straight from a New England calendar.
Burt Henry Covered Bridge
Sitting peacefully over the Walloomsac River, this bridge is another classic photo stop.
The reflections of fall colors in the water double the beauty.
Paper Mill Village Covered Bridge
This 1889 bridge has been carefully restored, and its rugged red timbers pop against the fall landscape.
Covered bridges are a quintessential part of Bennington’s identity, and October is the perfect time to hop from one to another.
Outdoor Hikes & Nature Walks
Mile-Around Woods Trail (North Bennington)
This easy, scenic loop trail is perfect for a morning foliage walk.
Winding through meadows and forests, it offers sweeping views of Mount Anthony and the surrounding valley.
Bennington Area Trail System (BATS)
A network of trails for hiking, biking, or even trail running.
In October, the forest canopy is painted with color, making even a short walk feel like a fall festival.
Harmon Hill Trail
For hikers who want a challenge, Harmon Hill delivers with steep climbs but epic rewards — sweeping valley views bursting with autumn color.
Bring water, good boots, and energy for this one.
Appalachian Trail / Long Trail
Bennington is lucky to sit near one of the most famous trails in America.
Even a short section walk in October brings you under fiery canopies and across crisp mountain ridges.
Insider Tip: Parking at the trailheads can be tight — arrive early to secure a spot.
Lakes, Parks & Scenic Drives
Woodford State Park
This high-elevation park is known for its quiet lake surrounded by evergreens and maples.
In October, the water mirrors the foliage like a painter’s canvas.
A peaceful spot for kayaking, picnicking, or just breathing in that crisp Vermont air.
Lake Shaftsbury State Park (Shaftsbury)
A smaller, more intimate lake park that feels cozy in fall.
The trails around the lake are easy and relaxing, with plenty of leaf-peeping spots.
Kelly Stand Road to Grout Pond (Scenic Drive)
If you want a foliage drive that feels wild and less touristy, this is it.
The dirt road winds through national forest and ends at Grout Pond, where golden leaves scatter across the water.
Farms, Orchards & Pumpkin Fun
The Apple Barn & Country Bake Shop
This is fall in Vermont in one stop.
Pick up cider doughnuts, fresh pies, maple syrup, and local cheeses — all while enjoying sweeping mountain views behind the barn.
Armstrong Farm (Pumpkin Patch)
Pumpkin picking is a must in October, and Armstrong Farm makes it extra fun.
With hayrides, farm stands, and piles of pumpkins, it’s a family-friendly fall favorite.
Shopping & Local Craftsmanship
Bennington Potters
This legendary pottery studio has been around since the 1940s.
From rustic mugs to dinnerware, everything is handmade and uniquely Vermont.
Watching the artisans at work is part of the charm.
Downtown Bennington Shopping
Stroll the downtown streets and explore shops like Hawkins House and Fiddlehead at Four Corners.
You’ll find Vermont crafts, quirky gifts, and plenty of cozy cafés to duck into between stores.
Foodie Stops & Sweet Treats
Madison Brewing Company
Bennington’s own brewpub serves hearty comfort food with craft beers brewed on-site.
It’s the perfect place to warm up after a chilly October hike.
Village Chocolate Shoppe
This family-owned shop is legendary for handmade chocolates, fudge, and truffles.
If you’ve got a sweet tooth, don’t leave Bennington without grabbing a maple truffle or caramel apple.
Conclusion
Bennington, Vermont in October is the perfect mix of heritage and foliage, cozy farm vibes and outdoor adventure.
From covered bridges and pumpkin patches to historic landmarks and mountain hikes, every corner feels like it’s glowing with autumn magic.
For the best experience, spend at least a weekend here and pair your trip with nearby Manchester or Dorset for a full Southern Vermont fall loop.
Share this content: