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Fall in Love with Bennington, Vermont: Beautiful Spots to Visit

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Ready to check out a few historic buildings and museums, a walkable downtown, and oodles of New England charm? Sure, this can describe lots of Vermont towns, but today we’re talking about the small, but bustling town of Bennington in the southwest corner of the state. Not only is Bennington a historic gem, but it’s incredibly beautiful in every season.

Oh, and did I mention that Bennington, Vermont is also my hometown?

Beautiful places in Vermont are pretty easy to come by, and the natural beauty in and around Bennington is what made me fall in love with it more than 15 years ago. In fact, I’ve lived in Bennington longer than anywhere else, and I can’t imagine calling any other place home, no matter how much I love to galivant around the country.

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.

Whether you’re looking for a girlfriend getaway, a romantic weekend for two, or a family vacation, Bennington, Vermont will not disappoint! The first thing you need to plan your trip to Bennington is a little inspiration, so I’m sharing seven of the most beautiful spots in town to encourage you to drop everything and plan your visit.

Ready to explore the oh-so-charming and welcoming town of Bennington, Vermont? Here are some amazingly beautiful places in my hometown, as well as some reasons that I think you should make a visit. 

How to Get to Bennington, VT

Bennington is located in the southwest corner of Vermont, basically right on the border of both New York to the west and Massachusetts to the south. It’s a pretty easy drive from anywhere in the northeast, which is why we recommend it as a great road-trip destination.

Pro Travel Tip: Give yourself 2-3 days to explore all of Bennington, especially if you love the outdoors. If you want to explore some of the surrounding towns like Wilmington or Manchester, plan for at least 4 days.

If you’re coming from out of state, the closest airport is Albany International, which is an easy one-hour drive from Bennington. Again, maybe it’s a biased opinion, but I adore flying in and out of the Albany Airport and always consider myself very fortunate that it is so close.

Why You Should Drop Everything and Visit 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 is Gorgeous in Just About Every Season

I say just about because I’m not terribly fond of mud season. I’ve lost whole boots to muddy quagmires in the month of March, and I’ve known others that have lost cars! Luckily, mud season in Vermont is short, lasting through March, and as long as we keep climate change at bay, I think I can handle it.

Lucky for us all of 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 in Vermont is known for the jaw-dropping foliage that blankets the forests and mountains in colorful displays. And winter, of course, is famous for skiing and snowboarding in the Green Mountains.

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

7 Beautiful Places to Visit in and around Bennington, Vermont

Have I convinced you to book your next vacation in Bennington yet? Well, let me sweeten the pot by sharing some of my favorite spots 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. I’ll admit that I’m an outdoor-lovin’ gal, so my favorite places reflect that.

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 in Bennington VT in the fall
The Old First Church in the fall

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 find yourself here in any season, be sure to check out the rest of Old Bennington. It’s like stepping back in time. You can even take a self-guided walking tour around town.

 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 when the church is open. 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 Vermont’s fall foliage season.

While you’re there, be sure to visit the grave of one of our most famous residents, Robert Frost, who is buried 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.

The Bennington Battle Monument in Old Bennington, VT

The Bennington Battle Monument
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.

The Bennington Monument was completed in 1889 to commemorate the Battle of Bennington, which took place on August 16, 1777. In that 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.

Historic tidbit: Although the battle is called the Battle of Bennington, it actually took place about 10 miles west in Walloomsac, New York.

Visitors can ride to the top of the Bennington Monument in an elevator from mid-April until October 31 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.

The green around the Bennington Monument is also one of my favorite spots for dog walking on a summer evening.

The Robert Frost House in Shaftsbury, Vermont

The Robert Frost House in Shaftsbury VT on a winter day
The Robert Frost House in Shaftsbury, VT

I’ve already mentioned that Mr. Frost is buried in Bennington, but he lived for a period in a little stone house in Shaftsbury, the next town over. The Robert Frost Stone House Museum is run by Bennington College and is open for visitors from Friday through Sunday from 10 am – 4 pm.

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.

Lake Shaftsbury State Park in Shaftsbury, VT

Lake Shaftsbury State Park in Shaftsbury Vermont during fall folliage season
Lake Shaftsbury in the fall

While you’re in Shaftsbury checking out the Robert Frost House, please take a walk around the lake at Lake Shaftsbury State Park.  This is a small, but gorgeous park, with a beach for swimming, great bird watching, and a really nice trail.

Dogs are welcome on the trails, making this one of our favorite spots for an evening stroll with the pups. 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. 

If you go during the open season (Memorial Day – the second Monday in October), the cost is $4 for adults and $2 for kids. During the off-season, you can park outside the gate and walk into the park. There are kayaks, canoes, and paddleboats available for rent in the summer.

Woodford State Park in Woodford, VT

Fall foliage in Woodford State Park
Woodford State Park in the fall

Another gem of a place, just 10 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.

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.

The Appalachian Trail in Bennington, VT

The Appalachian Trail footbridge in Bennington, VT in the fall
The Appalachian Trail footbridge over the Roaring Branch River in Bennington.

This famous long-distance trail runs across Route 9 between Bennington and Woodford, and there’s a parking area right off the road for hikers. The Appalachian Trail runs north and south across Route 9, but we prefer hiking south to Harmon Hill, for the beautiful views of Bennington.

The hike up to Harmon Hill starts off really steep for a good, heart pounding climb. After a mile or so, it levels off and travels through a high meadow, finally opening up to awesome views. The hike totals around 3 miles, with a total elevation gain of 1,000 feet.

If you hike north on the Appalachian Trail, you will 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 hike through the woods and worth checking out.

Park McCullough House in North Bennington, VT

Park McCullough House in North 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-Woods hiking trail all in one afternoon. This is one of my favorite places to walk and take pictures, and we always bring visitors from out-of-state here for picnics.

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, movies, wine tastings, and free yoga in the garden.

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. Vermont Begins Here is the tourism website for the town of Bennington, and the blog has ideas for where to eat, shop, and recreate.

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: Eat breakfast at the Blue Benn Diner (reopening soon), lunch at Madison Brewing Company, and dinner at either Allegro.

Where to stay -We love the Four Chimneys Inn for a splurge or a romantic getaway and the Harwood Hill Motel for a budget option. If you want to camp, we highly recommend Woodford State Park.

Finally, there are some really great rental deals on Airbnbs in the area. This renovated dairy barn in nearby Pownal has a pool and a hot tub, plus it’s great for kids and dogs!

Lloyd Baker, (Jimmy)

Thursday 4th of March 2021

I still call Bennington my only home, even though the last time I lived there was 1972 when my oldest was born. I was born in 1952 in Troy but my parents moved to Vermont when I was 1. My dad worked for the Rutland RR. Have a sister who lives on Silk Rd and many 1st realtives there. I could tell you many stories about growing up in Bennington and the fell of freedom that so many young people today don't know. Don't forget Grandma Moses in your writing.

Tara Schatz

Thursday 4th of March 2021

Thanks for your comment, Jimmy! Sounds like Vermont treated you well. I hope you come back and visit because it's still a really special place!

Virginia Moore

Tuesday 2nd of March 2021

I miss home I'm from Bennington as well but I moved to Tennessee 20 years ago because you're so much more to do

Tara Schatz

Tuesday 2nd of March 2021

Tennesee is lovely, and you can always come back for a visit!