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The photos in this post are taken from my Instagram account, which is very “Vermonty,” with a few other lovely places sprinkled throughout for good measure. Ready to explore the oh-so-charming and welcoming town of Bennington, VT? Here are some amazingly beautiful places in my hometown, as well as some reasons that I think you should make a visit.  

Woodford State Park is just a few miles from Bennington, VT

Exploring Bennington, VT

Until now, I’ve never really had a hometown. I’ve lived in dozens of places all over the country, never really settling in until I came here. I discovered this special place quite by accident thanks to house shopping on the internet. When we were looking to buy our first house back in 2006, we naturally spent hours each day browsing real estate websites. Eventually, we found ourselves looking at houses in Bennington, and we fell in love with a cute little bungalow. We never looked back, and have called Bennington home for the past 12 years. 

Headwaters Park in Bennington, Vermont

With just about 14,000 people, Bennington is a small town surrounded by rolling hills, the Green Mountains, farms, and forests. By Vermont standards, it’s 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 will definitely fall in love with Bennington, where you can hike, paddle, fish, and mountain bike without leaving town. Here are a few reasons why you have to visit Bennington, Vermont, as well as some beautiful spots that you won’t want to miss.

Bennington, Vermont is Gorgeous in Just About Every Season

Meyers Road, North Bennington/Shaftsbury Vermont

I say just about, because I’m not terribly fond of mud season. I’ve lost whole boots to muddy quagmires, and I’ve known others that have lost cars! Luckily, mud season in Vermont is short, lasting the month of March, and as long as we keep climate change at bay, I think I can handle it. Lucky for us, mud season goes hand-in-hand with maple sugaring season, so I guess that’s reason enough to cut it some slack! 

When you think of a typical Vermont vacation, you are likely thinking about fall and winter. Autumn for the jaw-dropping foliage that blankets the forests and mountains in colorful displays. And winter for the skiing and snowboarding in the Green Mountains. Bennington is a 45-minute drive from Bromley Mountain in Peru, Vermont and about an hour from Mount Snow in West Dover, Vermont. 

I love Vermont in every season, but there’s nowhere I’d rather be than here in the summer. We’ve got swimming holes. Creemee stands. Fireflies. Mountain Sunsets. Farmers’ markets. I just wish summer was longer!

Overlea Road, North Bennington, VT

7 Beautiful Places to Visit in and around Bennington, VT

I know I probably haven’t convinced you to book your vacation in Bennington, Vermont yet, but let me share some of my favorite places with you. The following spots are heavy on natural beauty, with a bit of history and pure New England charm thrown in for good measure. Whether you’re just passing through Bennington, or are making it your destination, these are spots you won’t want to miss. 

The Old First Church in Old Bennington, VT

The Old First Church, Bennington, Vermont

Judging by the number of tour buses and photographers I’ve seen at the Old First Church over the years, I think it might just be the most photographed building in New England. The Old First Church is  such a lovely place to explore, even if you’re not visiting during leaf-peeping season. If you do get to walk around the church, be sure to check out the rest of Old Bennington. It’s like stepping back in time.

 The Old First Church is the first gathered church in Vermont. Although the church that stands there now isn’t the original, it’s been around since 1805. Sunday worship takes place at 10 am during the summer months and 11 am during the rest of the year. You can also pop in for a tour with a local volunteer. The Old First Church is open for visitors every weekend  from Memorial Day to July 1st, and daily from July 1st to the end of foliage season.

While you’re there, be sure to visit the grave of one of our most famous residents, Robert Frost, which is located in the beautiful old graveyard between the Old First Church and the Bennington Museum, which is another great stop for lovers of both art and history.

Robert Frost’s grave behind the Old First Church, Bennington, Vermont

The Bennington Battle Monument

While you’re in Old Bennington, you won’t want to miss a tour of the Bennington Monument, which you can see from the Old First Church. At 306 feet, the Bennington Monument is the tallest building in the state. It’s the most popular of all Vermont state historic sites, and the views from the top are spectacular. Visitors can ride to the top in an elevator from mid-April until October 31st from 9 am to 5 pm.  Learn all about Bennington’s place in the Revolutionary War and be sure to have a picnic on the lawn.

A view of the Bennington Battle Monument from the Old First Church in Old Bennington

The Robert Frost House in Shaftsbury, Vermont

Mr. Frost is buried in Bennington, but he lived in a little stone house in Shaftsbury, the next town over. You can walk through his house in five minutes or so, but there’s also a beautiful nature trail that starts behind the barn and heads out to Lake Paran in North Bennington. The 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.

Lake Shaftsbury State Park

While you’re in Shaftsbury, please take a walk around the lake at Lake Shaftsbury State Park.  As of 2019, dogs are welcome on the trails, and in the summer you can go for a swim. The hike around the lake is just about a mile – it meanders through a gorgeous wetland, onto a ridge, and over two nice walking bridges. Lake Shaftsbury is also a great place to throw a line in and catch some trout. 

Early morning in the fall at Lake Shaftsbury State Park

Woodford State Park in Woodford, VT

Another gem of a place, just10 miles outside of Bennington, in the Green Mountains east of town is Woodford State Park. This is a quiet park with several nature trails, a small lake, and kayak/canoe rentals. Also, if you’re itching to go camping, Woodford State Park is where you want to do it. Sites are very private and some are located directly on the water. The lake at Woodford State Park is cold, even in summer, but it’s such a paradise! In my opinion, this is one of the most beautiful places in all of Vermont.

Fall at Woodford State Park

The Appalachian Trail in Bennington, VT

The famous long-distance trail runs across route 9 between Bennington and Woodford. There’s a parking area right off the road. The trail runs north and south, but we prefer hiking south to Harmon Hill, for the beautiful views of Bennington. It’s also easy to make a weekend of it by hiking through Glastenbury or to Bald Mountain. 

White birches on the Appalachian Trail in Bennington, VT

Park McCullough House in North Bennington, VT

This historic, Victorian-era house was built in 1864, and is considered one of the finest and best preserved Victorian mansions in New England. You can visit this beauty, the working farm behind it, and the lovely, Mile-Around-the-Woods hiking trail all in one afternoon. This is one of my favorite places to walk and take pictures, and we always bring visitors here.

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 concerts, plays, and puppet shows.

Park McCullough House photo credit: Angus McCullough

Park McCullough House in North Bennington/ photo credit: Angus McCullough

As usual, this post focuses almost entirely on outdoor excursions, but there are also cool museums, lots of shopping, and good restaurants in Bennington. If you decide to come to Vermont for a visit, feel free to contact me. I’d love to show you around!

Resources for Exploring Bennington, VT

What to do – The Bennington Chamber of Commerce has a great events page, plus lots of ideas for places to explore while you’re in the area.

Where to eat – Want some ideas for where to get some yummy grub? Bennington has lots of choices, but here’s what I’d recommend: For bread and baked goods head to Bakkerij Krijnen on East Main Street. Eat breakfast at the Blue Benn diner, lunch at Madison Brewing Company, and dinner at either Allegro on Main Street, or Pangaea in North Bennington.

Where to stay – Find the best hotels in Bennington by reading reviews on TripAdvisor. We love the Four Chimneys Inn for a splurge and the Harwood Hill Motel for a budget option. If you want to camp, we highly recommend Woodford State Park.

Want to read more about vacationing in Vermont? Check out these posts: 

• Why Farm Camping in Vermont Should be Your Next Adventure
• Exploring the Lake Champlain Islands with Vermont State Parks
• Winter Glamping in Vermont: Stay in a Geodesic Dome in Putney 
• Scenic Route 100: The Ultimate Vermont Road Trip Itinerary

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