10 Easy Road Trips Near Castleton Four Corners, Vermont (All Out of County)
If you’re based around
Castleton Four Corners in Rutland County, Vermont and itching to get out for the day, you’re in a sweet spot. In less than an hour or two of driving, you can be in some of the prettiest corners of
Vermont and nearby
New York.
This guide covers
10 short out-of-county road trips from Castleton Four Corners, focusing on nearby counties only:
- Addison County, VT
- Bennington County, VT
- Windsor County, VT
- Washington County, NY
No stops in Rutland County, no repeats of Castleton itself—just fresh destinations and fun things to do nearby.
1. Middlebury, VT – College Town Vibes & Covered Bridges (Addison County)
Distance from Castleton Four Corners: about
35–40 miles, roughly a
1-hour drive north.
Middlebury is one of those classic Vermont towns that feels like something out of a movie. There’s a small downtown, a college campus, and a river running right through the middle of it.
Things to do in Middlebury:
- Stroll downtown Middlebury – Check out local shops, bookstores, and cafes. Grab a coffee and just people-watch. It’s a simple pleasure, but it never gets old.
- Walk the Middlebury College campus – The campus is open and walkable, with beautiful old stone buildings and wide lawns.
- Hike around the waterfalls – Head toward the falls near downtown (Middlebury Falls) for photos and a short walk.
- Visit a covered bridge – There are classic covered bridges nearby, like the Pulp Mill Bridge, that make great quick stops for photos.
If you like a mix of
small-town charm and light adventure, Middlebury is an easy day trip from Castleton Four Corners.
2. Vergennes & Lake Champlain Views (Addison County)
Distance: about
50–55 miles, around a
1.25–1.5-hour drive northwest.
Vergennes calls itself Vermont’s smallest city, but don’t let that fool you—there’s plenty to do, especially if you love
water views.
What to do near Vergennes:
- Check out Vergennes Falls Park – A short walk from downtown takes you to a powerful waterfall on Otter Creek. It’s a great picnic spot.
- Drive toward Lake Champlain – Head west out of town for gorgeous views over the lake and the Adirondacks in New York.
- Explore local eateries – Grab a burger, a sandwich, or something sweet at one of the small restaurants lining Main Street.
If you time it right, watching the
sunset over Lake Champlain on your drive back can be the highlight of the day.
3. Brandon Gap & The Moosalamoo Region (Addison County side)
Distance: about
30–40 miles, roughly a
1-hour drive north/northeast, depending on the trailhead.
While Brandon itself is in Rutland County (so we’ll skip that), several hiking areas and trailheads lie in
Addison County on the other side of the ridge.
Ideas for outdoor lovers:
- Drive Route 73 over Brandon Gap – On the Addison County side, you’ll find trail access to the Long Trail and scenic pull-offs with big mountain views.
- Hike a short trail – Choose an easier trail if you’re just out for a few hours. Always check local trail maps and weather before heading out.
- Fall foliage drive – In late September and October, this route becomes a classic foliage drive, with bright reds and golds all around.
If you’ve ever wanted to feel like you’re driving through a postcard, this is your spot.
4. Manchester, VT – Shopping, Food & Mountain Views (Bennington County)
Distance: about
50–60 miles, around a
1.25–1.5-hour drive south.
Manchester is one of the most popular
day trips from Castleton Four Corners. It has a little bit of everything: outlets, good food, history, and mountain air.
Highlights in Manchester:
- Outlet shopping – Big-name outlets line the roads, making it easy to spend an afternoon browsing deals.
- Wander Manchester Village – White church steeples, grand inns, and quiet streets make for a relaxing walk.
- Drive up toward Mount Equinox – Even if you don’t hike, the drive gives you big, sweeping mountain views.
- Grab a local beer or coffee – Manchester has no shortage of places to refuel after exploring.
If you’re craving a mix of
retail therapy and fresh air, this road trip checks both boxes.
5. Bennington, VT – History, Arts & a Classic New England Feel (Bennington County)
Distance: about
65–75 miles, roughly a
1.5-hour drive south/southwest.
Bennington has that old New England charm you see in calendars—church spires, historic homes, and rolling hills.
Things to see in Bennington:
- Bennington Battle Monument (exterior grounds) – Even if you don’t go inside, the area around the monument offers sweeping views of the surrounding countryside.
- Drive the covered bridges route – There are several photogenic covered bridges in and around Bennington.
- Explore downtown – Browse local shops, bakeries, and galleries. It’s fun just to wander.
It’s the kind of place where you’ll want to slow down, walk a little more slowly, and just take it all in.
6. Woodstock, VT – Iconic Vermont Village (Windsor County)
Distance: about
60–70 miles, around a
1.5-hour drive east/northeast.
If you’ve seen pictures of classic Vermont villages, you’ve probably seen
Woodstock—it’s that pretty.
What to enjoy in Woodstock:
- Walk the village green – Historic homes, tidy lawns, and old trees surround the main green. It’s postcard-perfect.
- Browse downtown shops – Local art, Vermont-made goods, and cozy cafés are all within a few blocks.
- Scenic bridge views – Walk or drive over one of the area’s covered bridges for that classic photo.
Whether you’re into photography, slow travel, or just soaking in pretty scenery,
Woodstock is one of the best day trips near Castleton Four Corners.
7. Quechee, VT – Gorge Views & Glassblowing (Windsor County)
Distance: about
65–75 miles, roughly a
1.5-hour drive east.
Quechee pairs natural beauty with arts and crafts, making it a nice half-day or full-day outing.
Top things to do in Quechee:
- See Quechee Gorge (from overlooks and trails) – Often called “Vermont’s Little Grand Canyon,” it’s about 165 feet deep. There are short walks and views right from the bridge area.
- Watch glassblowing demos – Local glass studios and shops sometimes offer demonstrations and beautiful handmade pieces.
- Picnic by the river – Pack a simple lunch and enjoy it by the water on a nice day.
If you like a mix of
scenery and creativity, Quechee is a great choice.
8. Hanover, NH & Norwich, VT – College Town + Classic Village (Windsor County side)
Distance: about
75–85 miles, around a
1.5–2-hour drive east.
While Hanover itself is in New Hampshire, the Vermont side of the river—
Norwich in Windsor County—makes a fun road trip from Castleton Four Corners, especially if you like college-town energy.
What to do on the Vermont side (and just across the river):
- Stop in Norwich – A charming village with historic homes and a laid-back feel.
- Walk across to Hanover – Stroll around the Dartmouth College campus, enjoy shops and eateries, and soak up the student buzz.
- Enjoy the drive – The route along the Connecticut River is half the fun, especially when the leaves change color.
It’s a nice way to experience a slightly different vibe while still staying close to Vermont.
9. Lake George Region, NY – Classic Adirondack Fun (Washington County access)
Distance: about
40–60 miles, roughly a
1–1.25-hour drive west/southwest, depending on your route.
The main village of Lake George is actually in Warren County, NY, but you’ll likely pass through or near
Washington County, NY on your way there from Castleton Four Corners. It’s one of the most popular lake destinations within a day-trip radius.
Ideas for a Lake George area day:
- Lake views and beach time – Relax by the water, rent a small boat, or just walk the shoreline.
- Take a scenic drive – Drive along the lake and nearby backroads for rolling hills and Adirondack views.
- Arcades, ice cream & people-watching – The main village has a fun, casual vacation-town atmosphere.
If you’re craving that classic
summer lake trip feel, this is a great option out of Vermont for the day.
10. Rural Washington County, NY – Quiet Country Roads & Small-Town Charm
Distance:
20–50 miles, anywhere from a
30-minute to 1-hour drive west.
Sometimes the best road trip from Castleton Four Corners is simply heading into rural
Washington County, New York with no strict plan.
How to enjoy a “no-itinerary” drive:
- Pick a small town – Greenwich, Salem, or Cambridge are great starting points.
- Follow the backroads – Drive along farm fields, rolling hills, and quiet two-lane roads.
- Stop at farm stands – In season, you’ll find local veggies, maple products, and baked goods.
If you’ve ever wanted a slow, peaceful day with
no schedule and no stress, this kind of drive is perfect.
Tips for Planning Your Castleton Four Corners Road Trips
A few simple pointers to make these day trips smoother:
- Check drive times – Vermont and upstate New York roads are beautiful, but they’re often slower, winding two-lane routes.
- Watch the weather – Especially in fall, winter, and early spring. Conditions can change fast in the hills.
- Fuel up before you go – Some rural stretches don’t have frequent gas stations.
- Bring layers – Even in summer, evenings can cool off quickly.
One of my favorite memories in this region was a “quick” afternoon drive that turned into an all-day wander, just pulling over whenever something looked interesting—a farm view, a little bakery, a random antique shop. That’s the beauty of living or staying near Castleton Four Corners: you’re surrounded by easy adventures.
What’s Your Favorite Day Trip from Castleton Four Corners?
Have you tried any of these
short out-of-county road trips from Castleton Four Corners?
Do you have your own hidden-gem town, hike, or café in
Addison, Bennington, Windsor, or Washington County, NY?
- Drop a comment and share your favorite spot.
- Ask questions if you’re planning a visit and want more ideas.
- Share this post with friends or family who are looking for easy day trips near Castleton Four Corners.
The more we share our experiences, the easier it is for everyone to plan their next great little escape.
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