10 Easy Road Trips Near Wilder, Vermont (That Take You Out of Windsor County)
Planning a visit to
Wilder, Vermont and wondering what else is nearby? Or maybe you live in Wilder and want a few fresh ideas for a weekend drive. Either way, you’re in a great spot on the Vermont–New Hampshire border for quick
day trips and short
road adventures.
In this guide, we’ll skip anything in Windsor County itself and head out to surrounding areas in:
- Grafton County, NH
- Sullivan County, NH
- Addison County, VT
- Bennington County, VT
- Orange County, VT
- Rutland County, VT
- Windham County, VT
Most of these spots are within about 30 minutes to 2 hours of Wilder, making them perfect for
short road trips, leaf-peeping drives, or relaxed weekend escapes.
1. Hanover & Lebanon, NH – College Town Energy and River Views
Just across the Connecticut River in
Grafton County, New Hampshire, you’ve got a classic pairing: Hanover and Lebanon. It’s close enough to feel like an extension of Wilder, but it’s definitely outside Windsor County.
Here you can:
- Stroll around Dartmouth College in Hanover and people-watch on the green
- Walk along the Connecticut River or grab a bench and just enjoy the view
- Browse small shops and bookstores downtown
- Head to Lebanon’s Colburn Park area and explore local cafés and galleries
If you like the feel of a small college town with good coffee and walkable streets, this is an easy first road trip from Wilder. It’s the kind of place where you can spend half a day without ever checking your watch.
2. Quechee Gorge’s Neighbors: Hop Over to New Hampshire’s Side Roads
While Quechee Gorge itself is in Windsor County (so we’re skipping it), the
view from the New Hampshire side roads just across the river in
Grafton County can make a fun little drive.
Consider:
- Crossing into NH and following back roads that run parallel to the Connecticut River
- Pulling over at safe turnouts for river views and photos
- Packing a simple picnic and finding a quiet riverside spot
This isn’t a “big attraction” kind of trip. It’s more of a
slow-drive, windows-down kind of afternoon. If you like scenic drives more than crowded parking lots, this one might become your secret favorite.
3. Sunapee, NH – Lakeside Relaxing and Mountain Views
Head a bit farther east into
Sullivan County, New Hampshire, and you reach the
Lake Sunapee area. It feels like classic New England summer, but it’s fun any time of year.
Things to do around Sunapee:
- Walk the waterfront and watch the boats on Lake Sunapee
- Visit nearby Mount Sunapee Resort for hiking in summer or skiing in winter
- Take a short cruise on the lake in season, if they’re running
- Grab ice cream at a local stand (always a win after a hike)
If you like the idea of a lake day without driving all the way to the ocean, Sunapee is a nice fit. Picture clear water, mountain backdrops, and that laid‑back, flip‑flops vibe.
4. New London, NH – Small-Town Charm Near Colby-Sawyer College
Still in
Sullivan County,
New London offers another cozy small-town stop that pairs well with a Sunapee drive.
In New London, you can:
- Walk around the Colby–Sawyer College campus and nearby neighborhood streets
- Browse local shops for books, gifts, and outdoor gear
- Catch a show or event if the college or town has something going on
This is a great road trip if you like mellow places with friendly locals and easy parking. It feels like one of those towns where everybody knows each other—and doesn’t mind visitors one bit.
5. Middlebury, VT – Classic Vermont College Town in Addison County
Head northwest from Wilder and you’ll reach
Middlebury in
Addison County, Vermont. This is one of the state’s most loved small towns, and it makes a great day trip.
Highlights include:
- The campus of Middlebury College, with its stone buildings and open lawns
- The waterfall on Otter Creek right in the center of town
- Locally owned cafés, bakeries, and shops along the main streets
- Nearby back roads with farm and mountain views
If you time it right in fall, the drive up to Middlebury is half the fun. The foliage, old barns, and mountain views feel like a Vermont postcard come to life.
6. Addison County Back Roads – Lake Champlain Views Without the Crowds
Once you’re in
Addison County, keep going west toward
Lake Champlain for wide-open views and quiet country roads.
Consider:
- Driving out toward towns like Addison or Bridport
- Stopping at small roadside pull-offs to see the lake and the Adirondack Mountains across the water
- Exploring local farm stands in season for maple syrup, fresh produce, or baked goods
If you’re from the city, this area can feel surprisingly peaceful. You might see more cows than cars. And that’s kind of the point.
7. Manchester, VT – Shopping, Food, and Mountain Ambience
For a slightly longer road trip south into
Bennington County, Vermont, try
Manchester. It’s well-known, but it still feels like a mountain town.
In Manchester you can:
- Browse outlet shops and independent stores along the main drag
- Visit historic sites and old inns that give the town its classic New England look
- Use it as a home base to explore nearby hiking trails or scenic drives
It’s a good pick if your idea of fun is a mix of
a little shopping, a little walking, and a nice meal. Think cozy restaurants, mountain air, and a relaxed pace.
8. Bennington, VT – History, Art, and a Classic Vermont Town
Down in the same
Bennington County, the town of
Bennington offers a different feel than Manchester—more history, a bit more grit, but still very Vermont.
When you head to Bennington, you might:
- Walk through the historic downtown streets and check out local art
- Visit covered bridges in the surrounding area
- Drive the backroads for sweeping valley and mountain views
If you like towns with stories, old buildings, and a sense of place, Bennington is worth the extra miles from Wilder.
9. Rutland & Nearby Mountains – Gateway to Green Mountain Adventures
Travel west into
Rutland County, Vermont, and you’ll land in and around
Rutland, one of the state’s bigger towns.
Use Rutland as a jumping-off point to:
- Head toward ski areas in season, like the region around Killington and Pico
- Explore nearby hiking trails in the Green Mountains
- Check out murals and public art downtown
This road trip is a good option if you like a slightly more “lively” Vermont town, with chain stores mixed in with local spots, and quick access to the mountains.
10. Brattleboro, VT – Artsy Vibes Along the Connecticut River
Finally, drive south along the river to
Brattleboro in
Windham County, Vermont. It’s a bit of a trek from Wilder, but many people say it’s one of the most interesting towns in the state.
In Brattleboro, you can:
- Walk the main streets packed with bookstores, record shops, and cafés
- Explore local art galleries and small performance spaces
- Enjoy river views and nearby hikes
The town has a creative, slightly bohemian feel. If you like live music, handmade goods, and strong coffee, this one belongs on your list.
Tips for Enjoying These Short Road Trips from Wilder
To make the most of these
Vermont and New Hampshire road trips from Wilder:
- Check the weather before you go, especially in fall and winter
- Bring layers—mountain and lakeside areas can feel cooler than Wilder
- Fill up on gas in Wilder or a nearby larger town so you’re not hunting for stations on back roads
- Pack snacks and water so you can stop wherever the views are best
One of the best parts of staying in or near Wilder is how many different landscapes you can reach with just a short drive: lakes, college towns, artsy villages, and mountain valleys are all within reach.
What’s Your Favorite Road Trip from Wilder?
Have you taken any short drives from Wilder into
Grafton, Sullivan, Addison, Bennington, Orange, Rutland, or Windham counties?
- Which town surprised you the most?
- Do you have a “must-stop” café, trail, or lookout point?
I’d love to hear your ideas. Share your favorite out-of-county road trip from Wilder in the comments and help other travelers discover new places.
If you found this guide helpful, please
share it with friends or family planning a Vermont trip. The more we swap ideas, the better our road trips get.
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