10 Easy Road Trips From West Woodstock, Vermont (All Outside Windsor County)
If you’re based in
West Woodstock, Vermont and you’ve already hit all the local favorites, it might be time to hop in the car and explore a little farther. The good news? Within about 30–90 minutes, you can reach covered bridges, mountain views, classic Vermont towns, and even a few hidden gems most tourists miss.
Below are
10 short out-of-county road trips from West Woodstock, focusing on nearby spots in:
- Grafton County, NH
- Sullivan County, NH
- Addison County, VT
- Bennington County, VT
- Orange County, VT
- Rutland County, VT
- Windham County, VT
Each stop is perfect for a
day trip or an easy weekend getaway.
1. Hanover & Dartmouth College – Ivy League Vibes in Grafton County, NH
If you like small-town charm with a dose of culture, head to
Hanover, New Hampshire, just over the river in Grafton County.
Why go: It’s home to
Dartmouth College, which means great coffee shops, bookstores, and a lively downtown that still feels cozy.
Things to do:
- Stroll around the Dartmouth Green and people-watch.
- Visit the Hood Museum of Art (often free and surprisingly impressive).
- Walk a section of the Appalachian Trail, which runs right through town.
- Grab a latte and a pastry at one of the local cafes and sit by the window.
Driving tip: From West Woodstock, you can reach Hanover in around an hour, depending on your route and traffic.
2. Lebanon, NH – Riverfront Parks & Chill Downtown (Grafton County)
Just south of Hanover, you’ll find
Lebanon, New Hampshire, another Grafton County town that’s easy to visit in the same day.
Why go: It’s low-key, walkable, and has easy access to the Connecticut River and a nice town green.
Things to do:
- Walk around the Lebanon Town Green, especially if there’s a farmers market or concert.
- Explore nearby rail trails for biking or walking.
- Head down to the riverfront for a quiet stroll and some photos.
Make it a combo: Pair Hanover and Lebanon in one loop for a relaxed full day out of Windsor County.
3. Claremont, NH – Old Mill Town Charm (Sullivan County)
Looking for somewhere that feels more “real New England” than touristy?
Claremont, in Sullivan County, has that old mill town vibe.
Why go: Historic brick buildings, an old industrial feel, and river views give this town a rugged charm.
Things to do:
- Walk around the old mill district and check out the brick architecture.
- Head to the Connecticut River and nearby parks for a laid-back walk.
- Stop into a local diner or pub for a simple, hearty meal.
This is a good trip if you like poking around less polished, more authentic towns.
4. Newport & Sunapee Lake Area – Easy Lakeside Escape (Sullivan County, NH)
If you want water, views, and that “classic lake weekend” feel, point your car toward
Newport and the
Lake Sunapee area in Sullivan County.
Why go: It’s great for swimming in summer, leaf-peeping in the fall, and just relaxing by the water any time of year.
Things to do:
- Wander downtown Newport and grab a coffee or ice cream.
- Drive around Lake Sunapee and stop at public access points.
- In warmer months, look for boat tours or lakefront beaches.
If you’ve been craving a classic New England lake day, this is an easy win.
5. Middlebury, VT – College Town With Covered Bridges (Addison County)
Heading northwest brings you to
Middlebury in Addison County, one of Vermont’s most photogenic college towns.
Why go: It has waterfalls in the middle of town, a historic downtown main street, and a beautiful campus.
Things to do:
- Walk through downtown and over the bridge to see the falls on Otter Creek.
- Explore the Middlebury College campus and admire the stone buildings.
- Visit nearby back roads to find covered bridges and farm views.
- Sample Vermont cheese, cider, or maple treats at local shops.
If you like West Woodstock’s charm, Middlebury has that same cozy feeling on a slightly bigger scale.
6. Bristol & Lincoln Gap Area – Small Town, Big Mountain Views (Addison County)
A short drive from Middlebury, the town of
Bristol sits at the edge of the Green Mountains and makes a great base for a scenic drive.
Why go: Classic Vermont main street, mountain backdrop, and easy access to twisty roads and overlooks.
Things to do:
- Stroll downtown Bristol and pop into local shops.
- Drive toward Lincoln Gap for big views and winding mountain roads.
- Pack a picnic and find a pull-off to soak in the scenery.
If you love fall foliage, this area can feel like driving through a postcard.
7. Manchester, VT – Shopping, History & Mountain Backdrops (Bennington County)
Head southwest to
Manchester in Bennington County for a mix of outlet shopping, historic sites, and views of Mount Equinox.
Why go: It’s one of Vermont’s best-known small towns, with a little bit of everything.
Things to do:
- Browse the outlets and boutiques along Manchester’s main streets.
- Wander past grand old inns and historic homes.
- Drive up toward Mount Equinox for sweeping valley views.
This trip is ideal if your group has mixed interests—some can shop while others explore and take in the scenery.
8. Bennington, VT – Revolutionary History & Classic New England (Bennington County)
Keep going southwest and you’ll land in
Bennington, another Bennington County standout, packed with history and hometown pride.
Why go: Think small-city energy with old churches, charming streets, and that “real Vermont” feel.
Things to do:
- Walk around downtown Bennington and check out local cafes and shops.
- Visit historic neighborhoods with old homes and tree-lined streets.
- Drive to nearby viewpoints and back roads for sweeping rural scenes.
You can easily combine Manchester and Bennington in one longer day trip if you don’t mind a bit more driving.
9. Rutland, VT – City-Style Convenience, Vermont Attitude (Rutland County)
To the west,
Rutland in Rutland County offers more services and a bigger downtown while still feeling very Vermont.
Why go: It’s a good option if you want a larger selection of restaurants, shops, and events, plus easy access to the mountains.
Things to do:
- Stroll downtown Rutland and hunt for murals and public art.
- Visit local breweries or casual restaurants for a relaxed meal.
- Use Rutland as a base to explore nearby scenic drives and valleys.
This is a practical road trip when you want both
scenery and
convenience in one place.
10. Brattleboro, VT – Artsy, Edgy & Right on the River (Windham County)
For something a little different, point your car south toward
Brattleboro in Windham County.
Why go: It has an artsy downtown, independent shops, and a slightly quirky, creative energy.
Things to do:
- Walk along Main Street and pop into bookstores, galleries, and record shops.
- Check out the views of the Connecticut River from bridges and parks.
- Grab coffee or a local craft beer and just soak up the downtown vibe.
If you like places that feel a little offbeat and not overly polished, Brattleboro is a great match.
How to Choose Your Next Road Trip From West Woodstock
Not sure where to start? Here’s a simple way to decide:
- Love college towns? Try Hanover or Middlebury.
- Want lakes and water? Head toward the Newport / Lake Sunapee area.
- Craving shopping and dining? Go for Manchester, Brattleboro, or Rutland.
- Chasing mountain views and foliage? Aim for Bristol / Lincoln Gap or the roads between Manchester and Bennington.
- Want quieter, less touristy spots? Check out Claremont or some of the smaller Orange and Addison County back roads along the way.
Wherever you go, the beauty of starting from West Woodstock is that most of these trips are reachable in just a couple of hours or less. That means more time exploring and less time stuck behind the wheel.
Share Your Favorite Road Trips From West Woodstock
Have you taken any of these drives from
West Woodstock, Vermont? Did I miss a must-see stop in Grafton, Sullivan, Addison, Bennington, Orange, Rutland, or Windham County?
- Drop a comment with your favorite out-of-county road trip.
- Share this post with friends or family planning a Vermont getaway.
The more tips we share, the easier it gets for everyone to find new things to do near West Woodstock—without going too far from home.
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