10 Easy Road Trips from South Royalton, Vermont: Small-Town Adventures Just Beyond Windsor County
If you’re based in or near
South Royalton, Vermont and feel like stretching your legs (and your car’s mileage) a bit, you’re in the perfect spot. You’re close to the Green Mountains, the Connecticut River, and some of the most charming small towns in New England.
This guide shares
10 short out-of-county road trips to nearby Vermont and New Hampshire counties – all outside Windsor County – that make for simple, fun day trips or mellow weekend escapes.
1. Middlebury, VT – College Town Charm & Covered Bridges (Addison County)
About an hour northwest of South Royalton,
Middlebury feels like a classic New England movie set come to life. Think historic buildings, a gentle river, and a laid-back college vibe.
Why go: It’s a great mix of nature, culture, and good food.
- Stroll downtown along Main Street and check out local shops and cafes.
- Walk across the bridge to see the rushing falls on Otter Creek right in the center of town.
- Visit the Middlebury College campus for a peaceful walk, public art, and beautiful lawns.
- Hunt for nearby covered bridges like the Pulp Mill Covered Bridge on the outskirts of town.
If you’re into easy adventures, try a short walk along the
TAM (Trail Around Middlebury). Even just doing a mile or two gives you a taste of the local woods and fields.
2. Lake Dunmore & Branbury State Park – Classic Vermont Lake Day (Addison County)
Just south of Middlebury,
Lake Dunmore and
Branbury State Park serve up the kind of lake day you picture when you think “summer in Vermont.”
What to do at Branbury State Park:
- Relax on the sandy beach with mountain views.
- Swim in the clear lake water (perfect on a hot July afternoon).
- Rent a canoe, kayak, or paddleboard if you don’t have your own.
- Pack a picnic and grab a table under the trees.
If you like short hikes, there are nearby trails that offer small climbs and quiet forest time. It’s a simple, low-stress road trip that works for families, couples, and solo travelers.
3. Manchester, VT – Outlets, History, and Mountain Views (Bennington County)
Head about an hour and a half southwest into
Bennington County, and you’ll land in
Manchester, one of Vermont’s best-known getaway towns.
Highlights in Manchester:
- Shop the outlet stores and small boutiques spread along Main Street and Depot Street.
- Tour Hildene, the historic Lincoln family estate, with gorgeous grounds and mountain backdrops.
- Drive up nearby roads for views of Mount Equinox (and, in season, the Skyline Drive toll road).
Manchester is a good pick if your group can’t decide between shopping, walking, or just sitting with a coffee and people-watching. You can easily fill a full day without rushing.
4. Bennington, VT – Revolutionary War History & Small-Town Streets (Bennington County)
Further south in Bennington County,
Bennington offers a mix of history, art, and classic Vermont scenery.
Don’t miss:
- The Bennington Battle Monument – ride the elevator up for long-range views of Vermont, New York, and Massachusetts.
- Wandering Old Bennington with its historic homes and quiet streets.
- The Bennington Museum, known for local art and regional history exhibits.
On the way in or out of town, keep an eye out for several scenic
covered bridges scattered around the area. It makes for a fun mini driving tour if you like photography.
5. Hanover & Lebanon, NH – College Energy on the Connecticut River (Grafton County)
Cross the river into
Grafton County, New Hampshire, and you’ll hit the twin hubs of
Hanover and
Lebanon, roughly 35–45 minutes from South Royalton, depending on your route.
What to do in Hanover (home of Dartmouth College):
- Walk the Dartmouth College Green and explore the handsome brick buildings.
- Browse bookstores, cafes, and gear shops downtown.
- Stop by the Hood Museum of Art for a quiet, free dose of culture.
In
Lebanon, swing by the
Lebanon Green and stroll the nearby streets, or hop on a short stretch of the
Northern Rail Trail for a flat walk or bike ride.
This road trip is great if you want a mix of college-town buzz and easy walking paths without going too far from South Royalton.
6. Claremont & the Connecticut River Valley – Old Mill Town Vibes (Sullivan County, NH)
Just south of Lebanon in
Sullivan County,
Claremont, NH is a former mill town with brick factory buildings, a downtown square, and easy river access.
Ideas for your visit:
- Walk around the historic mill district by the Sugar River and old industrial buildings.
- Relax in the downtown square and check out local cafes or diners.
- Take a slow drive along the Connecticut River for views and small-town stops.
If you like “real-life” New England more than polished resort towns, this area gives you a grounded, lived-in feel, along with easy parking and low-key exploring.
7. Bradford & the Connecticut River Byways – Quiet New England Charm (Orange County, VT)
North of South Royalton in
Orange County, the town of
Bradford and the surrounding river towns are perfect when you’re in the mood for a slow day with no schedule.
Things to enjoy:
- Walk along Bradford’s main street and pop into local shops and bakeries.
- Drive the back roads near the Connecticut River for old farmsteads, fields, and mountain glimpses.
- Check out village commons and small parks in neighboring river towns.
This is the kind of road trip where you bring a thermos of coffee, roll the windows down, and just let the scenery roll by.
8. Killington & Pico – Mountain Playgrounds Beyond Ski Season (Rutland County, VT)
You probably know
Killington as a ski giant, but in
Rutland County it’s a four-season playground, about an hour or so from South Royalton.
Warm-weather ideas:
- Ride the scenic gondola (in season) for huge views from the top of the mountain.
- Hike one of the shorter trails around Killington or nearby Pico Mountain.
- Try mountain biking or just wander the base area if you’re not into intense activities.
Even if you’re not a skier, the drive up and the mountain air alone are worth the trip. Fall foliage here can be unreal, with fiery reds and golds across the ridges.
9. Downtown Rutland – Murals, Markets, and Local Flavor (Rutland County, VT)
Also in
Rutland County,
Rutland is a small city with a surprising amount going on, especially if you time it with a farmers’ market or local event.
In Rutland, you can:
- Walk the downtown streets and hunt for large-scale murals and public art.
- Check out local restaurants, breweries, and coffee shops.
- Visit nearby parks for a leg-stretching walk between stops.
If you’re used to tiny villages, Rutland gives you a little more “city” energy without the stress of big traffic or hard-to-find parking.
10. Brattleboro, VT – Artsy, Riverside, and a Bit Bohemian (Windham County, VT)
For a slightly longer but very rewarding drive, head south to
Brattleboro in
Windham County. It sits right on the Vermont–New Hampshire line along the Connecticut River.
Why Brattleboro is worth the trip:
- Vibrant downtown packed with bookstores, galleries, and quirky shops.
- Strong local food scene, from coffee to craft beer to global eats.
- Walks along the riverfront and side streets with plenty of people-watching.
Brattleboro has a creative, slightly bohemian feel that’s different from many other Vermont towns. If you like art, music, and interesting shops, this one belongs on your list.
Tips for Planning Your South Royalton Road Trips
To make these
Vermont and New Hampshire road trips from South Royalton smoother:
- Check drive times: Most of these spots are about 30–90 minutes away.
- Bring layers: Mountains and rivers can feel cooler, even in summer.
- Fuel up: Gas stations can be spread out once you’re off the main highways.
- Pack snacks and water: Especially if you plan hikes or long walks.
- Check seasonal hours: Some attractions, gondolas, and parks are seasonal.
You don’t need a packed schedule. Pick one or two highlights for the day, leave room for surprise stops, and let the back roads do their thing.
What’s Your Favorite Day Trip from South Royalton?
There are so many
things to do near South Royalton, VT once you wander into nearby counties like
Addison, Bennington, Orange, Rutland, Windham, Grafton, and
Sullivan. Whether you’re craving mountain views, lake days, small-town strolls, or college-town cafes, you can find it all within a short drive.
Have you taken any of these road trips?
Did I miss a must-see spot in these nearby Vermont or New Hampshire counties?
Share your favorite routes, stops, and hidden gems in the comments below—your ideas can help other travelers plan their next adventure.
And if you found this guide helpful, please
share it with friends or family who are planning a visit to Vermont. The more we swap stories and tips, the better our road trips get.
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