10 Easy Road Trips From North Bennington, Vermont: Iconic Things To Do Nearby
If you’re based in or near
North Bennington, Vermont and feel like you’ve seen every covered bridge and country lane in Bennington County, it might be time to head a little farther out.
The good news? Within about 30–90 minutes, you can dip into
Massachusetts, New York, and other parts of Vermont and find classic New England small towns, mountain views, farm stands, museums, and breweries—without committing to a full-blown vacation.
All of the ideas below are
outside Bennington County, in these nearby areas:
- Berkshire County, MA
- Franklin County, MA
- Rensselaer County, NY
- Washington County, NY
- Rutland County, VT
- Windham County, VT
- Windsor County, VT
So gas up the car, pack a day bag, and let’s hit the road.
1. Williamstown, Massachusetts: Art, Campus Vibes & Quiet Streets (Berkshire County)
Just about a 20–25 minute drive from North Bennington,
Williamstown, MA, feels like a classic college movie set, but with better art.
Top things to do:
- The Clark Art Institute – One of the country’s top art museums, tucked into the hills. Wander the galleries, then walk the trails behind the museum. Even the parking lot views are pretty.
- Williams College campus – Stroll the brick paths, admire the historic buildings, and duck into the small shops around Spring Street.
- Hopkins Observatory (if open) – Often called the oldest existing observatory in the U.S.; check ahead for visiting hours.
If you like a calm day of
art, architecture, and slow wandering, this is an easy, low-stress North Bennington day trip.
2. North Adams, Massachusetts: MASS MoCA & Mill Town Energy (Berkshire County)
A short hop past Williamstown,
North Adams has a more industrial, artsy feel. Old brick mills, big murals, and a creative vibe make it a fun contrast to sleepy Vermont villages.
Don’t miss:
- MASS MoCA – A massive contemporary art museum in an old factory complex. Even if you’re not “an art person,” the huge installations and funky exhibits are fun to wander through.
- Downtown murals – Take a slow walk and look up; the street art here is half the fun.
- Western Gateway Heritage State Park – Small, but interesting if you like railroad history and old engineering feats.
If you’re craving something different from barns and maple trees, North Adams feels a little bit like a mini Brooklyn dropped in the Berkshires.
3. Mount Greylock State Reservation: Summit the Highest Peak in Massachusetts (Berkshire County)
For a classic road-trip view, head to
Mount Greylock, about 45–60 minutes from North Bennington depending on your route. On a clear day, you can see up to 90 miles from the summit.
What you can do:
- Drive to the summit (seasonal) – The auto road winds up to the top, where you’ll find the stone Veterans War Memorial Tower and sweeping views.
- Hiking – Trails range from short walks to challenging climbs. The Appalachian Trail crosses the summit, too.
- Scenic picnic – Pack sandwiches and enjoy the cooler air and big sky feeling at the top.
If you’ve ever looked at the distant mountains from North Bennington and wondered what’s out there—this is your answer.
4. Shelburne Falls, Massachusetts: Bridge of Flowers & Small-Town Magic (Franklin County)
About 1.5 hours south from North Bennington,
Shelburne Falls is one of those towns that feels straight out of a postcard.
Highlights:
- Bridge of Flowers – An old trolley bridge turned into a lush, blooming garden walkway. It’s free to cross and perfect for photos.
- Glacial Potholes – Natural rock formations carved by ancient whirlpools in the Deerfield River. You can view them from town.
- Cute shops & cafes – Walk the quiet streets, browse local art, and linger over coffee or ice cream.
If you’re looking for an easygoing, romantic, or family-friendly day trip from North Bennington, this one checks all the boxes.
5. Bennington Battlefield & Hoosick Falls, New York: Revolutionary War History (Rensselaer County)
Head west into New York and you’ll hit
Hoosick Falls and the
Bennington Battlefield State Historic Site in about 25–30 minutes.
What to see:
- Bennington Battlefield – Learn about the 1777 Battle of Bennington (ironically, fought in New York). Walk the grounds, read the interpretive signs, and soak in the hilltop views.
- Hoosick Falls village – A small town with some historic architecture and a classic “upstate NY” feel.
If you like American Revolution history but don’t want a super formal museum experience, this is a relaxed, open-air way to do it.
6. Saratoga Springs, New York: Horses, History & Hot Mineral Springs (Saratoga County, near Washington County)
From North Bennington, it’s roughly an hour to
Saratoga Springs, but it’s one of the most rewarding out-of-county road trips you can make.
Must-dos:
- Saratoga Race Course (in season) – One of the oldest horse-racing tracks in the U.S. Even if you don’t bet, the atmosphere is fun and lively.
- Saratoga Spa State Park – Walk the trails, visit the mineral springs, and taste the (admittedly funky) mineral water straight from the spouts.
- Downtown Broadway – Boutiques, restaurants, and people-watching galore.
If you’re craving more nightlife and dining options than you’ll find in rural Vermont, Saratoga is your go-to.
7. Lake George Area, New York: Classic Adirondack Lake Day (Warren County, adjacent to Washington County)
While technically in Warren County, the
Lake George area is just beyond Washington County and makes an easy 1–1.25 hour trip from North Bennington.
Day-trip ideas:
- Lake cruises – Hop on a sightseeing boat for views of the mountains and shoreline mansions.
- Beach time – Relax on the public beaches, swim, and let the kids play.
- Prospect Mountain – Drive or hike up for sweeping views of the lake and Adirondack peaks.
Think of Lake George as your “instant summer vacation” when you only have a day to spare.
8. Manchester & Dorset, Vermont: Outlets, Marble Quarries & Mountain Views (Rutland County Adjacent)
While Manchester is still in Bennington County, heading a bit farther north puts you within reach of
southern Rutland County and its mountain attractions.
Ideas once you push past Manchester toward Rutland County:
- Scenic Route 7 drive – Continue north through the Green Mountains toward Rutland for changing views, especially in fall.
- Day extension to Rutland – Explore the city’s murals, farmers’ market (in season), and nearby trails.
Tip: Combine this with another stop such as Lake Bomoseen (see below) for a full, satisfying loop from North Bennington.
9. Lake Bomoseen & Castleton, Vermont: Easy Lake Escape (Rutland County)
About 1.5 hours from North Bennington,
Lake Bomoseen is the largest lake that sits entirely within Vermont. It’s a peaceful place for a no-fuss lake day.
What to do:
- Bomoseen State Park – Swim, picnic, paddle, or just sprawl out on the grass with a good book.
- Boating & kayaking – Rent a kayak or bring your own and explore the shoreline.
- Castleton village – Swing through this small college town for a bite or a short stroll.
If you want a quieter alternative to the busier New York lakes, this is a great option.
10. Brattleboro & Grafton, Vermont: Artsy River Town & Storybook Village (Windham & Windsor Counties)
Head southeast from North Bennington and within about 1.5 hours you can explore
Brattleboro (Windham County) and, a bit farther north,
Grafton (Windsor County).
In Brattleboro:
- Downtown arts scene – Galleries, quirky shops, used bookstores, and live music spots.
- Connecticut River views – Walk near the water and take in the bridges and hillsides.
In Grafton:
- Picture-perfect village – Historic inn, white church, and classic New England architecture.
- Cheese & local products – Look for local cheese, maple products, and handmade goods.
This combo makes a wonderful “slow travel” day: art and energy in the morning, quiet village charm in the afternoon.
Tips for Road-Tripping From North Bennington
To make these
North Bennington day trips even easier:
- Start with a theme – Are you in the mood for lakes, art, history, or shopping? Pick a road trip that matches your energy.
- Check seasonal hours – Places like Mount Greylock’s auto road, MASS MoCA exhibits, and Saratoga races can be seasonal or have special hours.
- Pack layers – Mountain and lakeside weather can change fast, even in summer.
- Bring snacks & water – Some of the back roads don’t have many stops.
I’ve found that the most memorable days are usually the simplest ones: a good drive, a few short walks, one great view, and something tasty to eat on the way home.
Where Will You Go Next From North Bennington?
You don’t need a long vacation to feel like you’ve “gone somewhere.” With these
10 short road trips from North Bennington, you can cross state lines, discover new towns, and still sleep in your own bed at night.
Which of these trips sounds best to you? Are you leaning toward
Lake George,
Saratoga Springs, or maybe a quiet wander through
Shelburne Falls?
- Drop your favorite idea (or your own hidden-gem suggestion) in the comments.
- If you know someone living in or visiting North Bennington, share this guide with them so they can start planning their own day trips.
The next great adventure might be just an hour’s drive away.
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