10 Relaxing Things To Do Near North Bennington, Vermont (That Locals Love Too)
If you’re dreaming of a quiet New England getaway,
North Bennington, Vermont is one of those small towns that feels like a secret. It’s tucked into the southwest corner of the state in Bennington County, close to the New York and Massachusetts borders.
You won’t find theme parks or giant malls here. Instead, you get covered bridges, mountain views, art, and that slow Vermont pace that makes you actually breathe again.
Whether you’re planning a weekend away from New York City, Albany, or Boston, here are
10 great things to do in and around North Bennington, VT that show off the best of this laid‑back corner of Vermont.
1. Wander the North Bennington Historic District
Start right in the heart of
North Bennington village. This compact historic district is easy to explore on foot and gives you a feel for real small‑town Vermont.
Stroll past:
- 19th‑century homes with wide porches and old stone foundations
- The charming village green and town buildings
- Views of the nearby hills and river
It’s the kind of place where you can grab a coffee, sit on a bench, and just people‑watch. I’ve spent entire late afternoons here doing nothing more than walking a loop, taking photos, and chatting with shop owners.
If you’re staying nearby, come back at different times of day—the village has a totally different feel in the early morning mist versus golden hour just before sunset.
2. Cross the Iconic Henry Covered Bridge
Vermont is famous for its
covered bridges, and one of the prettiest sits just outside North Bennington: the
Henry Covered Bridge (also called the Henry House Bridge).
Built in the 1800s, this classic red wooden bridge crosses the Walloomsac River. It’s still a working bridge, so you can drive or walk through it.
Here’s what to do there:
- Park nearby and walk slowly through the bridge
- Take photos from both sides – the angles look totally different
- Listen to the sound of the river below
In fall, the bridge is framed by bright reds, oranges, and yellows. In winter, it looks like a postcard scene with snow on the roof and ice along the riverbanks.
If you’re road‑tripping through Bennington County, this is an easy must‑stop.
3. Explore Bennington College’s Scenic Campus
Just a couple of minutes from the village,
Bennington College sits on a wide, open campus with rolling lawns, old trees, and mountain views. Even if you’re not a student, you’re usually welcome to walk the grounds respectfully.
Why it’s worth a visit:
- Beautiful views of the Green Mountains and nearby hills
- Interesting modern and historic buildings
- A calm, peaceful atmosphere
I like to park near the main entrance and walk gentle loops around campus. On clear evenings, the sunsets over the fields can be surprisingly dramatic for such a small place.
If you’re visiting in fall, bring a light jacket and wander until the light fades—the way the campus glows with color is something you don’t forget.
4. Visit the Park‑McCullough Historic Governor’s Mansion
One of the real gems in North Bennington is the
Park‑McCullough House, a grand 19th‑century Victorian mansion that once belonged to a wealthy Vermont family. It’s one of the best‑preserved Victorian country homes in New England.
What you can do here:
- Take a guided tour (seasonal) to see the richly decorated rooms
- Walk the gardens and grounds, which are lovely for photos
- Attend special events, concerts, or community gatherings when they’re scheduled
Even if the house isn’t open, the grounds are a peaceful place for a quiet walk. The mansion, carriage barn, and trees around it feel like stepping back in time.
If you enjoy historic homes, this is one of the top
things to do in North Bennington.
5. Walk (or Bike) the Rail Trail Along the River
North Bennington has access to simple, scenic
walking and biking paths that follow old rail lines and the river. They’re mostly flat, which makes them great if you’re traveling with kids or just don’t feel like climbing hills.
On these trails you can:
- Enjoy calm riverside views without traffic noise
- Spot birds, wildflowers, and maybe a deer if you’re lucky
- Take short, easy walks after breakfast or before dinner
If you’re used to city parks, walking here feels different. It’s quieter, and you can actually hear the water and the wind in the trees. It’s a perfect way to unwind at the end of a day of exploring Bennington County.
6. Spend an Afternoon in Downtown Bennington
Just a quick drive—about 10 minutes—south of North Bennington is
Bennington, the largest town in the county. If you want a little more going on, this is where you’ll find it.
In downtown Bennington you’ll find:
- Local cafes and bakeries (perfect for a maple latte or fresh pastry)
- Independent shops selling Vermont crafts, antiques, and gifts
- Art galleries featuring local and regional artists
It’s a good place to:
- Grab lunch after a morning walk in North Bennington
- Pick up Vermont maple syrup to take home
- Do a relaxed “shop and stroll” on a rainy or chilly day
Downtown Bennington has that old‑mill‑town feel: brick buildings, church steeples, and hills rising up around the edges.
7. Visit the Bennington Battle Monument
You can’t really visit Bennington County without seeing the
Bennington Battle Monument—you’ll spot it from a distance as you drive around.
This tall stone obelisk marks an important Revolutionary War battle and is the tallest human‑made structure in Vermont.
What to expect:
- Short walk from the parking area to the monument
- Option (seasonal) to go up in an elevator for wide views of Vermont, New York, and Massachusetts
- Historical markers explaining the Battle of Bennington
If you like history, this is a must‑do. Even if you don’t, the view alone is worth the stop on a clear day. Kids usually enjoy spotting the towns and hills below from the top.
8. Discover the Old First Church and Cemetery
Near downtown Bennington, the
Old First Church is a beautiful white clapboard church that looks exactly like what many people picture when they think “New England village.”
Right next to it is an old cemetery with weathered headstones and a quiet, slightly mysterious feel. The famous poet
Robert Frost is buried here.
You can:
- Walk quietly through the cemetery and read the old stones
- Visit Frost’s grave and read the words on his headstone
- Take photos of the church and grounds with the Green Mountains rising behind
It’s a peaceful, reflective stop. If you enjoy literature, this will likely be one of the more meaningful things you do in the area.
9. Taste Local Vermont Flavor: Maple, Cheese, and Farm Stands
One of the best parts of visiting small‑town Vermont is the food—not fancy, just fresh and local. In and around
North Bennington and Bennington, look for:
- Maple syrup stands – many local farms sell their own syrup and maple candy
- Cheese shops – Vermont cheddar here just hits differently
- Seasonal farm stands – in summer and fall you’ll find sweet corn, apples, berries, and homemade jams
If you’re driving country roads around Bennington County, keep an eye out for small hand‑painted signs at the end of long driveways. Those often lead to the best hidden spots for local honey, eggs, or syrup.
I always try to bring back at least one small bottle of pure Vermont maple syrup—it’s an easy, delicious souvenir that actually gets used.
10. Take a Scenic Drive Through Southern Vermont Backroads
One of the simplest—but most rewarding—things to do near North Bennington is to just
drive. The backroads in Bennington County are full of rolling fields, barns, rivers, and mountain views.
Here’s a simple loop idea:
- Start in North Bennington
- Head toward Shaftsbury and Arlington on local roads
- Circle back down toward Bennington and then return to North Bennington
Along the way you might find:
- Roadside farm stands
- Photo‑worthy barns and stone walls
- Pull‑offs with surprise views of the valley
In fall, this kind of drive becomes a full‑on foliage tour. But even in summer or winter, the quiet beauty of southern Vermont is hard to beat.
Tips for Visiting North Bennington, Vermont
A few quick tips to make your trip smoother:
- Best time to visit: Late September to mid‑October for foliage, but summer is great for walking, and winter is lovely if you like snow.
- Getting around: You’ll really want a car. Things are close in miles, but spread out in that classic rural Vermont way.
- What to pack: Comfortable walking shoes, layers (even summer nights can get cool), and a light jacket in shoulder seasons.
- Pace yourself: This isn’t a “see 12 attractions in a day” kind of place. It’s better enjoyed slowly.
Ready to Plan Your North Bennington Getaway?
North Bennington and greater Bennington County offer that old‑school Vermont charm that’s getting harder to find—quiet streets, friendly locals, historic homes, and easy access to nature.
From covered bridges and college greens to battle monuments and maple syrup, there’s plenty to fill a relaxed weekend or even a longer stay.
Have you been to North Bennington or anywhere in Bennington County?
I’d love to hear what you did, where you stayed, and what you’d recommend to other travelers.
- Drop your questions in the comments—thinking about visiting and not sure how to plan your time?
- Share this post with a friend who’s always saying they need a peaceful New England escape.
If you found this guide helpful, please share it on your favorite social media and leave a comment below with your own tips and experiences in North Bennington, Vermont!
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