South Shaftsbury, Vermont: 10 Scenic Short Road Trips Nearby

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10 Easy Road Trips From South Shaftsbury, Vermont: Best Things To Do Nearby

If you’re based in South Shaftsbury, Vermont and feel like getting out of town for the day, you’re in a great spot. You’re tucked right near the borders of New York, Massachusetts, and the rest of Vermont, which means a lot of fun day trips are less than a couple of hours away. Below are 10 short road trips from South Shaftsbury to nearby counties (but not Bennington County itself). We’ll explore Berkshire County, MA; Franklin County, MA; Rensselaer County, NY; Washington County, NY; and Rutland, Windham, and Windsor Counties in Vermont. All of these are out-of-county road trips, so you’ll really feel like you “went somewhere,” even if you’re home by dinner.

1. Williamstown, MA – Art, History & College-Town Vibes (Berkshire County)

Drive time from South Shaftsbury: about 20–25 minutes If you want a quick change of scenery without spending much time in the car, Williamstown in Berkshire County is an easy win. Things to do:
  • The Clark Art Institute – This museum is surprisingly world-class for such a small town. You’ll find European and American paintings, plus peaceful walking trails around the campus. Even if you’re “not a museum person,” the setting alone is worth it.
  • Williams College campus walk – Stroll through the college green, pop into the bookstore, and grab a coffee. College towns usually have a nice energy, and Williamstown is no exception.
  • Spring Street – This little main street is packed with cafes, restaurants, and shops. It’s a nice spot to wander, window shop, and grab lunch.
If you’re new to the Berkshires, Williamstown is a gentle introduction: cultured, walkable, and close to home.

2. North Adams, MA – Art in an Old Mill Town (Berkshire County)

Drive time: about 30–35 minutes Just a bit farther east, North Adams blends industrial history with modern art and mountain scenery. Don’t miss:
  • MASS MoCA – The Massachusetts Museum of Contemporary Art sits in a massive former factory complex. Even the building is cool to walk through. Exhibits change often, with big installations and quirky, thought‑provoking art.
  • Walk the downtown – Find murals, small galleries, and local diners. It still feels like a working town, which gives it character.
  • Natural Bridge State Park – See what’s said to be the only naturally formed white marble arch in North America. It’s a short walk, easy for most ages.
North Adams makes a fun day trip if you like art, photography, or just exploring old mill towns that are finding new life.

3. Mount Greylock – Highest Peak in Massachusetts (Berkshire County)

Drive time to main access points: about 45–60 minutes If you’re craving mountain views but want something different from the Green Mountains, head to Mount Greylock, the highest point in Massachusetts at about 3,491 feet. What to do on Mount Greylock:
  • Drive to the summit – In season, you can drive up to the top. On a clear day, you may see up to 90 miles in several directions.
  • Hike a short trail – There are easy to moderate hikes, so you don’t need to be a hardcore hiker to enjoy it.
  • Bascom Lodge – At the summit, this rustic lodge usually offers food, drinks, and sometimes events. Check ahead for hours and season dates.
For anyone in South Shaftsbury, Mount Greylock is a perfect “mini-adventure” that still gets you home by nightfall.

4. Shelburne Falls, MA – Bridge of Flowers & Charming Village (Franklin County)

Drive time: about 1 hour 15 minutes–1 hour 30 minutes Head southeast into Franklin County, Massachusetts to discover Shelburne Falls, a small town with big character. Highlights:
  • Bridge of Flowers – A former trolley bridge now covered with flowers from spring through fall. It’s short but lovely, and one of those places that’s surprisingly relaxing.
  • Glacial Potholes – In the river below, nature carved smooth circular holes into the rock. It’s a quick stop but fun to look at, especially if you like geology or photography.
  • Village shops & cafes – Browse local crafts, grab ice cream, or linger over coffee. The town has a laid‑back, artsy feel.
This trip is especially nice if you enjoy scenic drives, historic towns, and easy strolls rather than full‑on hikes.

5. Troy, NY – Farmers Market, Food & Riverfront (Rensselaer County)

Drive time: about 45 minutes–1 hour Head west from South Shaftsbury into New York and you’ll hit Troy, in Rensselaer County, a friendly small city along the Hudson River. Why go to Troy?
  • Troy Waterfront Farmers Market – Often held outdoors in warmer months and indoors in winter, this market is packed with local produce, baked goods, crafts, and more. It’s a great place to spend a Saturday morning.
  • Historic downtown – Troy has beautiful old brick buildings and plenty of independent shops, coffee spots, and restaurants.
  • Hudson River views – Walk along the riverfront area to unwind after lunch or grab photos.
If you’re in the mood for more food options and city energy than you’ll find in most Vermont towns, Troy is a solid choice.

6. Grafton Lakes State Park – Woods, Lakes & Easy Trails (Rensselaer County)

Drive time: about 40–50 minutes Not far from Troy, Grafton Lakes State Park offers a classic day in the woods: water, trails, and picnic spots. Things to enjoy:
  • Swimming and beaches (in season) – Relax by the water or go for a swim when the weather is warm.
  • Paddling – Bring a kayak, canoe, or paddleboard and explore the small lakes at your own pace.
  • Walking and hiking – There are trails for different levels, from easy loops to longer walks, great for families or casual hikers.
If you like Lake Shaftsbury but are looking for a slightly different scene without going too far, this park is a nice alternative.

7. Lake George, NY – Classic Adirondack Getaway (Washington County & Beyond)

Drive time: about 1 hour 15 minutes–1 hour 30 minutes Heading north‑northwest, you’ll cross through Washington County, New York on your way to the famous resort area of Lake George. Top experiences:
  • Lake cruises – Take a boat tour to see the shoreline and islands. It’s a great way to get the feel of the Adirondacks without hiking miles into the woods.
  • Beach and village – Enjoy the public beach, walk the strip, and check out souvenir shops, arcades, and ice cream stands.
  • Hikes and viewpoints – If you want a bit more adventure, there are short hikes nearby with great lake views.
Lake George can feel a bit touristy, but in a fun, carefree way. It’s perfect if you’re craving a “mini vacation” in a single day.

8. Rutland & The Vermont Marble Museum Area (Rutland County)

Drive time: about 1 hour–1 hour 15 minutes To the north of Bennington County lies Rutland County, home to the small city of Rutland and several interesting side stops. Ideas for your day:
  • Downtown Rutland – Check out local shops, grab a bite, and walk past a growing collection of murals and public art.
  • Nearby Rail Trails – The area has bike and walking paths built on old rail lines, which makes for easy, mostly flat exploring.
  • Vermont Marble Museum in Proctor (check hours) – Learn how marble shaped the region and see examples used across the country. It’s a quirky, very “Vermont” kind of stop that’s more interesting than it sounds on paper.
For South Shaftsbury locals, Rutland offers a slightly more urban feel, but still has that Vermont charm.

9. Brattleboro, VT – Artsy River Town Near the New Hampshire Line (Windham County)

Drive time: about 1 hour–1 hour 15 minutes Head southeast into Windham County and you’ll find Brattleboro, a creative, colorful town along the Connecticut River. Why visit Brattleboro?
  • Downtown galleries & bookstores – This town has a strong arts scene: galleries, music spots, and independent bookstores are all within walking distance.
  • Food & coffee – From farm‑to‑table restaurants to casual sandwich joints, there’s a lot of choice for such a small place.
  • River and nearby trails – Enjoy river views or head just outside town for short hikes and scenic overlooks.
Brattleboro is a good road trip if you enjoy people‑watching, local art, and a slightly bohemian vibe.

10. Woodstock, VT – Picture‑Perfect New England Village (Windsor County)

Drive time: about 1 hour 30 minutes–1 hour 45 minutes Finally, if you’re up for a slightly longer drive, WoodstockWindsor County is one of the most classic Vermont towns you can visit. What to see and do:
  • Village green & covered bridges – Walk around the historic center, admire the old homes, and visit one of the nearby covered bridges.
  • Shops and galleries – Browse local crafts, outdoor gear shops, and art galleries. It’s an easy town to just wander.
  • Nearby farms and trails – There are working farms and short hikes in the surrounding hills if you want more time in nature.
Woodstock is great for anyone looking for that postcard‑perfect New England feel: white church steeples, stone walls, and tidy village streets.

Tips for Planning Your South Shaftsbury Road Trips

To make the most of these out‑of‑county adventures from South Shaftsbury:
  • Check seasonal hours – Museums, mountain roads, and parks often have limited seasons or hours, especially in winter and early spring.
  • Pack layers – Weather in Vermont, New York, and Massachusetts can shift quickly. A light jacket or extra sweater never hurts.
  • Bring snacks and water – Especially if you’ll be hiking or driving back roads where services are limited.
  • Start early – You’ll beat the crowds at popular spots like Lake George, Mount Greylock, and Woodstock, and have more relaxed time in each place.
From art museums in Massachusetts to lakes in New York and charming Vermont villages, you don’t have to go far from South Shaftsbury to feel like you’ve really traveled.

Share Your Favorite Road Trips From South Shaftsbury

Do you have a favorite day trip from South Shaftsbury that’s outside Bennington County? Maybe a hidden swimming hole, a tiny café in a neighboring town, or a scenic overlook you think more people should know about? I’d love to hear from you. Drop your tips, questions, or trip ideas in the comments so other travelers can discover new places too. And if you found this guide helpful, please share it with friends or family who are looking for easy weekend road trips near South Shaftsbury, Vermont.
Location: Georgetown, IN, USA

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