Looking for covered bridges, art, and charming New England vibes? I always say—head to Bennington, Vermont! The first time I visited, I was drawn in by the historic homes and quiet streets, but it’s the local art scene and natural beauty that keep pulling me back. You’ll stroll past colonial churches, explore indie galleries, and maybe even catch a mountain view framed by a classic red barn. Whether I’m hiking or gallery hopping, Bennington always leaves me inspired—and I think it’ll do the same for you.
Best Time to Visit
Personally, I love visiting between May and October. Summer brings warm days perfect for exploring Main Street or hiking nearby trails. And fall? You’ll find some of the best foliage in the region—I’ve driven through town on golden October afternoons and just had to pull over for photos. Winter has its own magic too, with snow-covered charm and access to nearby ski spots. If you’re looking for peace and blooming countryside, spring is beautifully quiet and fresh.
How to Get There
- By Car: I usually drive in on U.S. Routes 7 or 9—it’s about 3.5 hours from NYC and around 2.5 from Boston or Albany. You’ll love the backroads and rolling hills on the way in.
- By Train: I’ve taken Amtrak to Albany before and rented a car from there. It’s just about an hour’s drive to Bennington. You can also use the Brattleboro station if you're coming from the east—it’s roughly 90 minutes away.
- By Plane: Albany International Airport (ALB) is the closest major airport. I’ve flown in a few times—it’s an easy, scenic drive to Bennington from there.
Where to Stay
- The Four Chimneys Inn: I stayed here once and didn’t want to leave. It’s a beautifully restored mansion with elegant rooms and peaceful grounds—you’ll feel tucked away but still close to everything.
- South Shire Inn: This inn is full of Victorian charm, and I’ve recommended it to anyone who loves antiques and character. It’s right in the heart of historic Old Bennington—you’ll love the walkable surroundings.
- Paradise Inn: When I’m traveling with family or looking for a laid-back stay, this is my go-to. It’s casual, centrally located, and the gardens and pool make it feel like a retreat.
Top Attractions in Bennington
Step Into Colonial History at the Old First Congregational Church of Bennington -
Take in Panoramic Views from the Iconic Bennington Battle Monument -
Explore Vermont Art, History, and Grandma Moses at the Bennington Museum -
Stroll or Snap Photos at the Picturesque Silk Covered Bridge -
Admire the Craftsmanship of the Historic Burt Henry Covered Bridge -
Enjoy Live Performances at the Oldcastle Theatre Company -
Tour Victorian-Era Grandeur at the Park-McCullough Historic House -
Visit the Scenic Paper Mill Village Bridge Over the Walloomsac River -
Experience the Unique Campus and Culture of Bennington College -
Grab a Bite and Local Vibe at Kevin's Sports Pub and Restaurant -
In Summary...
(and if you want to revisit my photo journey)- • Step Into Colonial History at the Old First Congregational Church of Bennington
- • Take in Panoramic Views from the Iconic Bennington Battle Monument
- • Explore Vermont Art, History, and Grandma Moses at the Bennington Museum
- • Stroll or Snap Photos at the Picturesque Silk Covered Bridge
- • Admire the Craftsmanship of the Historic Burt Henry Covered Bridge
- • Enjoy Live Performances at the Oldcastle Theatre Company
- • Tour Victorian-Era Grandeur at the Park-McCullough Historic House
- • Visit the Scenic Paper Mill Village Bridge Over the Walloomsac River
- • Experience the Unique Campus and Culture of Bennington College
- • Grab a Bite and Local Vibe at Kevin's Sports Pub and Restaurant