10 Fun Road Trips Near Saxtons River, Vermont (Outside Windham County)
If you’re staying in or around
Saxtons River, Vermont and feel like getting out of town for the day, you’re in luck. Within about 30–90 minutes, you can explore covered bridges, mountain views, classic New England towns, and even a few quirky surprises.
The key here: every suggestion below is
outside Windham County, but still an easy drive from Saxtons River. Think of this as your go-to list of
short road trips from Saxtons River into nearby counties like
Windsor, Bennington, Cheshire, Sullivan, and Franklin County, MA.
1. Woodstock, VT – Classic New England Charm (Windsor County)
Woodstock is the kind of place you see on postcards. It’s about an hour or so northwest of Saxtons River, depending on your route, and it makes for a perfect day trip.
What to do in Woodstock:
- Walk around the village green and browse little shops.
- Visit Billings Farm & Museum for a taste of Vermont farm life.
- Stroll the Middle Covered Bridge for those classic photos.
- Grab a maple latte or local pastry at a downtown café.
On one visit, I spent almost an hour just watching folks sit on benches and enjoy ice cream on a warm afternoon. It felt like stepping into a slower, kinder world.
2. Quechee Gorge – “Vermont’s Little Grand Canyon” (Windsor County)
Just west of Woodstock, you’ll find
Quechee Gorge, one of the most popular natural attractions in Vermont. It’s an easy drive from Saxtons River and pairs nicely with a stop in Woodstock.
Why it’s worth the drive:
- Stand on the bridge and look down into the gorge, about 165 feet deep.
- Take the short hike down to the river for a different view.
- Check out nearby shops and the Quechee Gorge Visitor Center.
If you’re nervous about heights, just take your time crossing the bridge. The view is stunning, especially in fall when the foliage lights up the whole valley.
3. Hanover, NH – Ivy League Energy in a Small Town (Grafton/near Cheshire & Sullivan area)
Cross over into New Hampshire and head to
Hanover, home of Dartmouth College. It’s a lively little town with a fun mix of students, locals, and visitors.
Things to do in Hanover:
- Walk around the Dartmouth Green and campus.
- Browse the college bookstore and local shops.
- Walk along the Connecticut River or find nearby trails.
- Grab lunch or coffee at one of the Main Street cafés.
The town has that mix of higher education and small-town life you don’t see everywhere. It’s great if you enjoy people-watching and a bit of culture without big-city stress.
4. Keene, NH – A Walkable Downtown With a Big Green (Cheshire County)
< b>Keene in Cheshire County is a laid-back New Hampshire city that’s still small enough to feel friendly. It’s a nice choice if you want more dining options and an easy walking downtown.
Highlights in Keene:
- Stroll Central Square and the wide Main Street.
- Check out local bookstores, antique shops, and bakeries.
- Visit the Colony Mill Marketplace area (check what’s open before you go).
- Look for seasonal events or festivals on the town calendar.
I once ducked into a random café here during a rainstorm and ended up chatting with a local about the best foliage drives. That’s the kind of place Keene is—easy to talk to strangers, easy to slow down.
5. Mount Ascutney & Ascutney State Park – Views Without Huge Crowds (Windsor County)
If you’re craving some mountain time,
Mount Ascutney is a manageable option not too far from Saxtons River.
What you can do:
- Drive up the mountain road (seasonal) to a parking area and hike to the summit.
- Explore miles of hiking trails with varying difficulty.
- Enjoy picnic areas in Ascutney State Park.
The summit offers big views without requiring a hardcore all-day climb. Bring a jacket—even in summer, the breeze up there can surprise you.
6. Manchester, VT – Outlets, Art, and Mountain Views (Bennington County)
Head west toward
Manchester in Bennington County for a mix of shopping, history, and scenery. This makes a great trip if you’re traveling with a group that likes different things.
In Manchester you can:
- Shop the outlets and local boutiques.
- Visit Hildene, the Lincoln family home (Robert Todd Lincoln’s estate).
- Drive or hike around the Green Mountains nearby.
- Enjoy cozy restaurants with mountain views.
It’s one of those towns where you can dress casual or a little fancy and feel right at home either way.
7. Bennington, VT – History, Art, and a Big Monument (Bennington County)
Another solid road trip from Saxtons River is the town of
Bennington. It has a strong sense of Vermont history and a mellow, artsy vibe.
Don’t miss:
- The Bennington Battle Monument – take the elevator up for wide-angle views.
- The trio of Bennington covered bridges in the area.
- Bennington Museum for regional art and local stories.
If you love old New England cemeteries and historic spots, you’ll find plenty here—just remember to be respectful as you wander.
8. Claremont & the Sugar River Area – Underrated Small-Town Escape (Sullivan County)
In Sullivan County,
Claremont, NH often flies under the radar, but it’s a nice low-key destination if you prefer simple walks and river views over crowds.
Ideas for your Claremont day trip:
- Walk by the Sugar River and check out old mill buildings.
- Explore the compact downtown and look for local coffee or lunch spots.
- Find nearby trails or short walks along the water.
It’s not a polished tourist town, but that’s part of its charm—less pressure, more room to just explore.
9. Shelburne Falls, MA – The Bridge of Flowers (Franklin County, MA)
Head south into
Franklin County, Massachusetts and discover
Shelburne Falls, a village that punches way above its size when it comes to charm.
Top things to see:
- The famous Bridge of Flowers – a former trolley bridge turned garden you can walk across.
- The Glacial Potholes – natural rock formations in the river.
- Small galleries and shops along the main streets.
If you love photography, you could easily spend hours here. Between the flowers, the water, and the old brick buildings, every corner looks like a picture.
10. Greenfield, MA – Gateway to the Pioneer Valley (Franklin County, MA)
Also in Franklin County,
Greenfield makes a nice stop if you want a bigger town feel with access to nature.
In and around Greenfield:
- Drive up to Poet’s Seat Tower for views over town.
- Check out local shops, bookstores, and cafés downtown.
- Use Greenfield as a base to explore other Pioneer Valley towns.
This is a good option if you’re road-tripping with friends and want a flexible day with food, views, and wandering all rolled into one.
Tips for Planning Your Saxtons River Road Trips
A few simple things can make these short drives even better:
- Check the season: Some mountain roads and attractions are seasonal, especially in mud season or winter.
- Watch the drive time: Most of these spots are within about 1–1.5 hours of Saxtons River, perfect for a day trip.
- Pack layers: Weather shifts fast in Vermont and New Hampshire, even in summer.
- Bring cash: A few small places still prefer cash for parking or small purchases.
If you love scenic drives, try linking a couple of these places together—for example, Woodstock + Quechee Gorge, or Manchester + Bennington on the same day.
Share Your Favorite Day Trips from Saxtons River
Have you taken any of these
short road trips from Saxtons River? Did I miss a must-see spot in
Bennington, Windsor, Cheshire, Sullivan, or Franklin County?
I’d love to hear from you.
Drop your favorite stops, hidden gems, or questions in the comments.
And if you found this guide helpful, please
share it with friends or family planning a Vermont getaway—sometimes the best adventures start with a simple day trip just beyond your own backyard.
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