10 Unforgettable Short Road Trips from Bellows Falls, Vermont

10 Easy Road Trips From Bellows Falls, Vermont: Fun Things To Do Nearby

If you’re in Bellows Falls, Vermont and feel like going for a drive, you’re in a sweet spot. In less than an hour or so, you can cross into New Hampshire or Massachusetts, or head deeper into Vermont and discover covered bridges, farm stands, mountain views, and classic New England towns. This guide shares 10 short out-of-county road trips from Bellows Falls to nearby spots in:
  • Cheshire County, NH
  • Sullivan County, NH
  • Bennington County, VT
  • Windsor County, VT
  • Franklin County, MA
Each one is an easy day trip with simple things to do, good food, and that cozy New England vibe.

1. Keene, New Hampshire – A Classic New England Downtown (Cheshire County)

About a 40‑minute drive from Bellows Falls, Keene is the kind of town that makes you want to slow down and wander.
  • Stroll around the Keene Central Square with its church steeples and brick buildings.
  • Check out local shops along Main Street for books, gifts, and outdoor gear.
  • Grab coffee at a cozy cafĂ© and people‑watch from a sidewalk table.
  • Walk or bike part of the Cheshire Rail Trail if you want a bit of exercise.
On a fall afternoon, the whole place feels like a movie set, with leaves crunching under your boots and the smell of wood smoke in the air. If you like low‑key road trips, Keene is an easy win.

2. Mount Monadnock & Jaffrey, NH – Big Views For A Half-Day Hike (Cheshire County)

If you’re craving a little challenge, head about an hour southeast to Mount Monadnock, one of the most-climbed mountains in the world.
  • Choose a marked trail from the Monadnock State Park headquarters in Jaffrey.
  • Bring sturdy shoes, water, and layers—the top can be windy even on sunny days.
  • Plan 3–5 hours round-trip depending on your pace and route.
The rocky summit gives you wide‑open views of New Hampshire, Vermont, and even into Massachusetts on a clear day. If you’ve been sitting at a desk all week in Bellows Falls, this hike is like hitting a reset button for your brain.

3. Walpole, New Hampshire – Farm Stands & River Views (Cheshire County)

Just across the Connecticut River and about 20 minutes from Bellows Falls, Walpole is small, scenic, and perfect for a slow afternoon.
  • Wander the village green and admire the historic homes.
  • Visit a local farm stand for fresh apples, maple syrup, or baked goods in season.
  • Drive quiet back roads with views of the Connecticut River Valley.
This is a good stop when you don’t want a full-day adventure—just a simple drive, some scenery, and maybe a bag of fresh cider donuts for the ride home.

4. Claremont, New Hampshire – Old Mills & Riverside Walks (Sullivan County)

Head about 35–40 minutes north to Claremont, a former mill town on the Sugar River that’s slowly reinventing itself.
  • Walk near the old mill buildings and river for a mix of history and industrial charm.
  • Explore the downtown area with its shops and restaurants.
  • Check for local events or markets—you’ll sometimes find live music or fairs on weekends.
Claremont isn’t polished like some tourist towns, but that’s part of its appeal. It feels real, and it’s a nice change of pace from the quieter Vermont side of the river.

5. Sunapee & Lake Sunapee – Lakeside Escape (Sullivan County)

Looking for water views and an easy lakeside getaway? Drive about an hour to Lake Sunapee and the nearby town of Sunapee.
  • In summer, relax at a public beach or take a boat cruise if available.
  • Enjoy small-town charm in Sunapee Harbor with ice cream, shops, and benches by the water.
  • In winter, hit the slopes at Mount Sunapee if you like skiing or snowboarding.
If Bellows Falls feels landlocked some days, Lake Sunapee is your quick fix for that “lake vacation” feeling—without needing a full week off.

6. Woodstock, Vermont – Picture-Perfect Village (Windsor County)

About 50 minutes northwest of Bellows Falls, Woodstock might be one of the most beautiful towns in Vermont.
  • Walk the covered bridge right near the village center.
  • Browse local galleries, boutiques, and general stores.
  • Visit nearby historic farms and sugarhouses for classic Vermont flavor.
  • Take a slow drive through the countryside—almost every bend in the road is a photo moment.
If you’re hosting out‑of‑state friends or family in Bellows Falls and want to impress them, Woodstock is a safe bet. It’s pure postcard New England.

7. Quechee Gorge – Vermont’s “Little Grand Canyon” (Windsor County)

Just past Woodstock, about an hour from Bellows Falls, you’ll find Quechee Gorge, a deep, dramatic cut in the earth carved by the Ottauquechee River.
  • Walk across the bridge on Route 4 and look down into the gorge.
  • Hike the short trail down to the riverbed for a different view.
  • Browse nearby shops and grab a snack or picnic supplies.
The gorge is one of those places that’s impressive in every season—green and lush in summer, colorful in fall, and starkly beautiful in winter.

8. Bennington, Vermont – History, Art & A Tall Monument (Bennington County)

Head about an hour west to Bennington, a town full of history and small-city energy.
  • Visit the towering Bennington Battle Monument for views over the area.
  • Explore Old Bennington with its historic homes and peaceful cemetery where poet Robert Frost is buried.
  • Check out local art galleries and museums if you enjoy culture and history.
  • Drive out to see one or more covered bridges in the area for that classic Vermont photo.
Bennington works well as a full day trip from Bellows Falls: scenic drive, sightseeing, food, and plenty of spots to stretch your legs.

9. Wilmington & The Mount Snow Area – Mountains & Reservoir Views (Bennington County)

About 1 to 1.25 hours southwest, the Wilmington and Mount Snow area gives you mountain and lake scenery in one go.
  • Stroll through Wilmington’s village with its shops and cafes.
  • Enjoy views of Harriman Reservoir; in warmer months you can kayak, paddleboard, or just relax by the water.
  • In winter, head to Mount Snow for skiing and snowboarding.
  • Take a scenic drive on nearby back roads for sweeping valley and mountain views.
If you like Bellows Falls but wish it had a few more mountain peaks in the background, this trip scratches that itch.

10. Greenfield, Massachusetts – Easy City Feel Without Big-City Stress (Franklin County)

About 50–60 minutes south, Greenfield gives you a slightly busier vibe while still feeling small and manageable.
  • Walk the downtown area with its mix of shops, restaurants, and local businesses.
  • Drive or hike up to Poet’s Seat Tower for a wide view over the town and surrounding hills.
  • Look for local festivals, farmers’ markets, or live music—Greenfield often has something going on.
If you’re craving a change from small-village Vermont but don’t want Boston-level traffic, Greenfield is a comfortable middle ground.

Tips For Enjoying These Bellows Falls Road Trips

To make the most of these short getaways from Bellows Falls:
  • Check the weather before you go, especially for hikes and mountain trips.
  • Bring cash—some farm stands and small shops still prefer it.
  • Plan your timing so you’re not driving unfamiliar back roads too late at night.
  • Layer your clothing—New England weather changes fast, even within an hour’s drive.
Think of Bellows Falls as your home base. In less time than it takes to watch a movie, you can be in a totally different landscape: lakeside, mountainside, small city, or farm country.

Share Your Favorite Road Trips From Bellows Falls

Have you taken a fun day trip from Bellows Falls to any of these places in Vermont, New Hampshire, or Massachusetts? Did I miss a spot in Cheshire, Sullivan, Windsor, Bennington, or Franklin County that you absolutely love?
  • Leave a comment and share your favorite nearby road trip.
  • Tell us your go‑to coffee stop, hiking trail, or scenic overlook.
  • Share this post with friends or family who are planning a visit to Bellows Falls and looking for things to do nearby.
The more local tips we collect, the easier it is for everyone to plan simple, memorable getaways from this little corner of Vermont.

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