This Small Vermont Town is Perfect for History and Outdoor Lovers
Note: Advertising is how we keep this site free for you to enjoy, and we earn a commission from affiliate links that may be included in this post. Thank you for supporting Vermont Explored!
Looking for a Vermont destination with a walkable downtown, great restaurants, intriguing shops, and lots of outdoor recreation?
Not only does Bennington, Vermont, cover all of these bases, but it’s incredibly easy to get to from metropolitan areas in the Northeast.
Located just three and a half hours from New York City, three hours from Boston, and an hour from Albany, Bennington is the gateway to Vermont and well worth a visit, no matter where you’re coming from.
I may be biased, but I think Bennington is one of the loveliest places to visit in all of Vermont.
Bennington VT: At-A-Glance
Here’s a bite-sized snapshot of everything you need to know to plan your trip!
- When to Go: May through October is lovely in this part of Vermont
- Where to Stay: For an upscale getaway within walking distance of downtown Bennington, choose South Shire. There are nine delightful rooms housed in a beautiful Victorian home, plus a delightful Thai restaurant on site — Niramet.
- Top 3 Highlights: Bennington Museum, a covered bridge tour, and Park McCullough House.
Of course, beautiful places in Vermont aren’t hard to come by, and the natural beauty in and around Bennington is what made me fall in love with it two decades ago. No matter how much I love a good road trip, I can’t imagine calling any other place home!
Here’s an overview of the best things to do in Bennington, Vermont, for your next getaway, as well as our top choices for lodging and dining in Bennington.
The Best Things to Do in Bennington, Vermont
With just over 14,000 people, Bennington, VT, is a small town bookended by two mountain ranges, the Taconics and the Greens. By Vermont standards, Bennington is actually a big town — the sixth largest in the state. Bennington is the county seat and a hub of activity in Southwestern Vermont.
If you love the outdoors, you’ll fall in love with Bennington, where you can hike, paddle, fish, and mountain bike without leaving town. If you’d rather spend your days browsing shops, sipping craft beers, and learning about New England history, Bennington is the ideal spot for your next weekend trip.
Take a Self-Guided Walking Tour of Old Bennington
While located entirely in the town of Bennington, a visit to Old Bennington is a bit like stepping back in time. This historic village is home to fewer than 200 people, along with beautiful historic buildings, and a colorful past.
Whether you’ve lived in the area for years or are visiting for the first time, there’s a lot to discover on an Old Bennington walking tour.
The oldest home on the tour is the Jedidiah Dewey House, built in 1763. The homes on the tour are all private residences, but it’s fun to meander past them as you tour Monument Avenue.
The Old First Church (pictured above) was built in 1805 and is one of the most beautiful and recognizable churches in Vermont.
Download a walking tour brochure to get started on your journey.
Also Read: Plan a Perfect Winter Weekend in Bennington and Manchester, Vermont
Eat Breakfast at a Historic Diner
Bennington is home to some fantastic eateries, but one of the most unique is the historic Blue Benn Diner on North Street.
The Blue Benn was manufactured in the late 1940s by The Paterson Vehicle Co. and shipped and assembled here in Bennington in 1948. The diner was owned by Sonny and Marlou Monroe for many decades, starting in 1973, and just recently came under new ownership.
Blue Benn serves up classic diner fare along with a few eclectic choices. There are still jukeboxes on every table and plenty of room for you to rub elbows with the locals at the bar.
The Blue Benn is open from Tuesday to Sunday, from 6 am – 2 pm.
Tour Bennington’s Beautiful Covered Bridges
Bennington County is fortunate enough to have five historic covered bridges, and they can all be explored in a single afternoon.
These beautiful feats of engineering offer a one-of-a-kind look into a bygone age — a time when ingenious craftsmanship was used to create structures that embodied simple beauty and embraced the natural landscape.
A covered bridge road trip is the perfect way to spend your afternoon. If you do this trip in the summer, you’ll find great swimming under both Arlington bridges, but fall and winter are beautiful, too.
Start by visiting the three covered bridges in Bennington and then drive north to Arlington to see the other two:
- Silk Road Covered Bridge
- Paper Mill Covered Bridge
- Burt Henry Covered Bridge
- Chiselville Covered Bridge
- Arlington Green Covered Bridge
For a complete guide to discovering the covered bridges in Bennington County, read this next:
Go Antiquing
The Bennington area is home to several wonderful antique stores, and two are located right on Main Street, making it easy to walk between them as you search for the one-of-a-kind prize you never knew you needed.
If you’re a fan of antiquing, then Bennington is bound to entice your inner treasure hunter. Check out the following shops:
- Main Street Antiques: 473 Main Street, Bennington
- Monument Vintage: 435 Main Street, Bennington
- Covered Bridge Antiques: 2026 Route 7A, Bennington
Discover Vermont History and Art at the Bennington Museum
There’s more than one reason to check out Bennington Museum – thought-provoking history and art exhibits, intriguing special events, and even an outdoor nature trail. But Bennington Museum is probably best known for housing the largest collection of Grandma Moses paintings in the world.
Anna Mary Robertson started painting in her seventies and became one of America’s most prolific and famous self-taught artists within just a few years. Come visit the Grandma Moses schoolhouse as well as many artifacts from her painting life.
Bennington Museum presents and explores the rich culture of southern Vermont, eastern New York State, northwestern Massachusetts, and southern New Hampshire in all its forms from the 18th century to the present.
Visit on Friday evenings for Concerts in the Courtyard between June 3 and September 2, when the museum is open until 7 pm.
Take in the View from the Bennington Battle Monument
At 306 feet, the Bennington Battle Monument is the tallest building in the state, and it’s the most popular of Vermont’s state historic sites.
If you visit between May and October, you can take an elevator to the top for spectacular views of Bennington and the Green Mountains.
The Bennington Monument was completed in 1889 to commemorate the Battle of Bennington, which took place on August 16, 1777. In the famous battle, Brigadier General John Stark and 1,400 New Hampshire men defeated two detachments of the British army, who were seeking to capture a store of weapons and food maintained where the monument now stands.
The victory at the Battle of Bennington is celebrated each year across Vermont as a state holiday.
The Bennington Monument is open daily between May 1st and October 31st from 10 am to 5 pm.
Historic tidbit: Although the battle is called the Battle of Bennington, it actually took place about 10 miles west in Walloomsac, New York.
Visit the Former Home and Grave of a Famous Vermont Poet
Did you know that Robert Frost lived in both Bennington and Ripton, Vermont?
His Bennington/Shaftsbury home is now the Robert Frost Stone House Museum. Frost lived here from 1920 to 1929 when he wrote “Stopping by Woods on a Snowy Evening.”
While visiting this literary landmark, be sure to walk the grounds and perhaps the beautiful nature trail that starts behind the barn and heads out to Lake Paran in North Bennington.
The Robert Frost Trail is 2 miles (one-way) and meanders through the woods and along stone walls. It’s easy to envision Robert Frost walking these same country trails before heading home to pen some of his most famous works.
After visiting the Robert Frost House, drive back into Old Bennington, where you can pay your respects to Robert Frost at his gravesite behind the Old First Church.
Hike a Part of the Oldest Long-Distance Trail in America
Vermont’s Long Trail was the first long-distance hiking trail in the United States and the inspiration for the much longer Appalachian Trail.
This 272-mile trail follows the ridgeline of the Green Mountains from the Vermont-Massachusettes state line in the south to the Canadian border in the north.
The Appalachian Trail/Long Trail shares a path from roughly 100 miles through Vermont before diverging near Killington. The trail crosses Route 9 in Woodford, Vermont.
If you hike south, you can reach Harmon Hill in about 1.5 miles. The hike starts off steep, but after a mile or so, it levels off and travels through a high meadow, finally opening up to awesome views of Bennington. The hike totals around 3 miles, with a total elevation gain of 1,000 feet.
If you hike north on the Long Trail, you’ll head up Maple Hill in the Glastenbury Wilderness. This is another steep hike but without the view at the end. Still, it’s a lovely trek through the woods and is worth checking out.
Paddle a Quiet Lake or River Near Bennington
Canoeing and kayaking are both great ways to enjoy the outdoors in Vermont, and there are several small lakes and rivers around Bennington that are perfect for paddling.
If spending a few hours on the water is your idea of a perfect afternoon, check out these spots.
*Note that Lake Shaftsbury and Woodford State Park both offer canoe and kayak rentals.
- Lake Paran – Lake Paran is a small, 35-acre lake in North Bennington with easy access for canoes and kayaks. The shore is undeveloped and the scenery is lovely. Use the boat launch on State Fishing Acc off of North Street in North Bennington.
- Lake Shaftsbury State Park – Lake Shaftsbury encompasses 26 acres with a wetland on one end that is great for birding. This is a popular park for summer visitors who come to swim, picnic, and relax on the sandy beach.
- Woodford State Park – The 23-acre Adams Reservoir is located in Woodford State Park at 2,310 feet above sea level. The shoreline is entirely wooded and there are a couple of private coves that are fun to explore. Be on the lookout for sundews, a carnivorous plant that grows on logs in the marshy part of the lake.
- Walloomsac River – If you don’t mind doing some car shuffling, the Walloomsac River is a nice easy paddle for a warm day. Put in at the Henry Bridge in North Bennington and paddle downstream to the Edward Cottrell Bridge at the intersection of Cottrell Road and Route 67 in Hoosick Falls, New York.
Drink Up at a Local Brewery or Distillery
Vermont takes its beer very seriously, and Bennington is no exception. Not only does the town host two homebrew festivals each year, but a couple of local breweries make exceptional beers as well.
If you love craft beer, visiting these local breweries is one of the best things to do in Bennington, VT, after hours.
- Harvest Brewing: 201 South Street, Bennington. Open Thursday – Saturday, hours vary.
- Madison Brewing: 428 Main Street, Bennington. Open Monday – Saturday, 11:30 am – 9 pm, and Sunday, 11:30 – 4:30 pm.
Tour Park McCullough House in North Bennington
Park McCullough House is a historic Victorian-era mansion that was built in 1864. It is considered to be one of the finest and best-preserved Victorian mansions in New England. Visit this beautiful house-turned-museum, the beautiful grounds, and the Mile-Around-Woods hiking trail for an adventurous afternoon.
This is one of my favorite spots to walk our dogs and take photos, and we always bring visitors from out-of-state here for picnics. Give yourself a few hours to tour the mansion and the grounds.
Park McCullough House is open for tours on weekends from summer until the end of fall foliage season. Admission is $15 per person. Special events are also hosted throughout the summer and include yoga on the lawn, concerts, and plays.
Follow us on social media for more Vermont inspiration!
