10 Fun Things To Do Near South Shaftsbury, Vermont (Bennington County)
If you’re looking for a quiet Vermont escape with easy access to small-town charm, mountain views, and covered bridges,
South Shaftsbury in Bennington County is a great home base.
This tiny village doesn’t shout for attention, but that’s part of the magic. Within a short drive you’ll find classic New England scenery, historic sites, local food, and plenty of outdoor adventures.
Below are
10 things to do near South Shaftsbury, VT, perfect for a weekend getaway or a longer Vermont road trip.
1. Visit the Robert Frost Stone House Museum
Just up the road in Shaftsbury, you’ll find the
Robert Frost Stone House Museum, a must-see for literature lovers and curious travelers alike.
This 18th‑century stone farmhouse was once home to poet Robert Frost. He wrote some of his most famous work while living in this area, including the poem “Stopping by Woods on a Snowy Evening.”
Inside, you’ll find:
- Exhibits about Frost’s life and writing process
- Original manuscripts and photos
- A peaceful garden and walking areas behind the house
It’s a small museum, but that’s what makes it special. You can take your time, read the displays, and actually hear the birds outside instead of city traffic.
If you enjoy quiet, thoughtful places, this is one of the best
things to do near South Shaftsbury.
2. Explore Old Bennington & the Bennington Battle Monument
About 10–15 minutes from South Shaftsbury is
Old Bennington, one of the most historic villages in Vermont.
The star here is the
Bennington Battle Monument, a 306‑foot stone obelisk that towers over the town. It commemorates an important American victory during the Revolutionary War.
You can:
- Ride an elevator to the top for sweeping views of Vermont, New York, and Massachusetts
- Walk around the base and read about the battle
- Stroll nearby streets lined with classic New England homes and churches
On a clear day, the view from the top is amazing—rolling hills, church steeples, and miles of green. It’s one of the best
scenic viewpoints in Bennington County.
3. Visit Robert Frost’s Grave in Old Bennington
While you’re in Old Bennington, walk over to the
Old First Church and its peaceful cemetery. Here you’ll find the grave of Robert Frost, marked by a simple stone with his famous line,
“I had a lover’s quarrel with the world.”
Even if you’re not a big poetry fan, the setting is beautiful:
- Quiet grounds with old headstones and stone walls
- Views of the Bennington Battle Monument
- A classic white New England church building
It’s a reflective stop, and only a short drive from South Shaftsbury. This makes a nice pairing with the
Robert Frost Stone House Museum—you can see where he lived and where he rests, all in one afternoon.
4. Walk or Bike the Walloomsac River Trails in Bennington
If you enjoy easy walks by the water, head into Bennington and look for the
Walloomsac River area. Several short trails and riverfront paths make great spots for:
- Casual walks with kids or dogs
- Short bike rides
- Picnics by the water
Sections of the
Bennington Area Trail System (BATS) also connect nearby for those who want something a bit more adventurous, from mellow woods walks to steeper hikes.
This is a nice option if you want to stretch your legs after a long drive but aren’t looking for a full-on mountain trek.
5. Drive the Scenic Back Roads Around South Shaftsbury
You don’t always need a big attraction to enjoy Vermont. Sometimes the best activity is simply
driving the back roads around South Shaftsbury.
Expect:
- Rolling farms and old barns
- Stone walls and maple trees lining the roads
- Mountain views that seem to pop up around every corner
If you visit in the fall, the foliage can be stunning—bright red, orange, and yellow across the hills. In winter, everything turns into a snow globe scene.
Take your time, pull over safely to snap photos, and just enjoy the peaceful, rural side of
Bennington County, Vermont.
6. Hunt for Covered Bridges Nearby
Vermont and covered bridges go hand in hand, and the
South Shaftsbury / Bennington area has several within a short drive.
Some worth seeking out include:
- Papermill Village Bridge – Near North Bennington, with a classic red exterior.
- Silk Road Bridge – A photogenic bridge over the Walloomsac River.
- Henry Bridge – Another charming spot for photos and river views.
You can turn it into a mini covered bridge tour. Plot a loop from South Shaftsbury and see how many you can visit in one afternoon.
Tip: Early morning or late afternoon often gives you the best light for photos.
7. Explore Downtown Bennington’s Shops and Cafes
When you’re ready for coffee, a meal, or some browsing, head to
downtown Bennington, about 10 minutes from South Shaftsbury.
You’ll find:
- Locally owned cafes and bakeries
- Antique shops and bookstores
- Art galleries and small boutiques
This is a good place to grab:
- A hearty breakfast before a day of exploring
- A relaxed lunch with Vermont-made cheese or maple syrup dishes
- A casual dinner after visiting the monument or museums
If you like small-town main streets with character, downtown Bennington is a comfortable, walkable hub close to South Shaftsbury.
8. Visit the Bennington Museum
Just outside Old Bennington, the
Bennington Museum offers a deeper look into the region’s history and art.
Inside, you can explore:
- Revolutionary War artifacts
- Folk art and regional paintings
- Exhibits about Vermont industry and daily life
The museum is also well known for its collection related to painter
Grandma Moses, who lived nearby. Her rural scenes feel especially fitting when you step back outside into the Vermont countryside.
This is one of the top
indoor things to do near South Shaftsbury, especially on a rainy or chilly day.
9. Take a Day Trip to Manchester, Vermont
If you don’t mind a scenic 25–30 minute drive north,
Manchester, VT makes a great day trip from South Shaftsbury.
In Manchester, you can:
- Shop at outlets and local boutiques
- Visit the American Museum of Fly Fishing
- Tour Hildene, the Lincoln family home, with gorgeous grounds and views
The drive from South Shaftsbury to Manchester takes you through pretty stretches of
Bennington County, with mountains on both sides. It’s an easy way to add more variety to your
South Shaftsbury, Vermont getaway.
10. Enjoy Seasonal Farm Stands, Orchards, and Maple Treats
Depending on the time of year, the area around South Shaftsbury comes alive with classic Vermont treats.
Keep an eye out for:
- Farm stands selling fresh vegetables, berries, jams, and baked goods
- Apple orchards in the fall with pick‑your‑own apples and cider donuts
- Maple syrup producers offering tastings and bottled syrup to take home
Stopping at a small, local stand can be one of the most memorable parts of a Vermont trip. There’s something special about chatting with the person who actually grew or made what you’re buying.
If you’re planning a
South Shaftsbury weekend trip, it’s worth checking local listings or asking your inn or host what’s in season.
Final Thoughts: Why South Shaftsbury Makes a Great Base
South Shaftsbury itself is quiet, but that’s exactly why it works so well as a base for exploring
Bennington County:
- You’re close to historic Old Bennington and the Bennington Battle Monument.
- You can easily reach Robert Frost landmarks and museums.
- Scenic drives, covered bridges, and small-town main streets are all nearby.
If you’ve been looking for a low-key corner of Vermont with plenty to do within a short drive,
South Shaftsbury is worth adding to your list.
Share Your South Shaftsbury Experience
Have you visited South Shaftsbury or the Bennington area?
- What was your favorite covered bridge or scenic drive?
- Did you stop at the Robert Frost Stone House or the Bennington Battle Monument?
Drop your stories, tips, and questions in the comments—and if you found this guide helpful, please
share it with friends or family planning a Vermont getaway. Your share helps more travelers discover this quiet, beautiful corner of the state.
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