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Have you ever seen a photo of a little white church against green or fiery orange mountains and thought, “okay, where exactly is that?” Nine times out of ten, the answer is Vermont.
Vermont is by far one of the most beautiful states in the USA and when it comes to small town charm, it knows what it’s doing!
Covered bridges, maple syrup, creemees and main streets that look like film sets… this is what you should expect!
One heads up: I visited in summer, when everything was green and gorgeous. But almost every town here is even more spectacular in the fall, when the foliage kicks in. If you can time your trip for late September or October, do it, and book your accommodation early.
Here are my 10 favorite small towns in Vermont.
1. Stowe
📍 Highlights: Mount Mansfield, Stowe Community Church, the Trapp Family Lodge, the Stowe Recreation Path, Smugglers’ Notch
Stowe is a place I had been dying to visit for years, and it didn’t disappoint for a second!
The photos you can see on the internet are so pretty that it’s easy to assume that it won’t be as good as it seems. Well, it was even better than it seemed!!
When you get to Stowe, park on the main street. It’s free and you get 3 hours to explore the town which should be enough.
From the main street, head to the ‘Welcome to Stowe’ mural for photos.
From there, walk another couple of minutes to the covered bridge and up to the Stowe Community Church viewpoint. That white spire against the mountains is the most iconic shot in Vermont, and it’s unreal in the fall.
From there, you can take the recreation path which is located behind the movie theater nearby and walk to the church and up and down the main street.
Just outside town, the Von Trapp Family Lodge (yes, the Sound of Music family, who still own it) looks like a corner of Austria, with highland cows and an excellent brewery.
And if you do one scenic drive in Vermont, make it Smugglers’ Notch on Route 108, stopping at Bingham Falls.
For dinner, I really liked The Ranch Camp as you could eat outside and see the top of the spire of the church.
2. Montpelier
📍 Highlights: the Vermont State House, Hubbard Park and its observation tower, Morse Farm Maple Sugarworks, downtown Main Street
Montpelier is wildly overlooked, and I honestly don’t understand why because that was one of my favourites!
It’s the smallest state capital in the entire US, with around 8,000 people, and here’s my favorite fact for you: it’s the only state capital in America with no McDonald’s, and no Starbucks within the city limits either. In the 1990s the city actually turned McDonald’s away. Very Vermont.
The State House is the centerpiece, with a gold-leaf dome and Greek Revival columns.
Vermont chose Montpelier as its capital in 1805, and this is the third State House, completed in 1859 after the second burned down.
Free tours are also offered in summer and in the fall.
Across the road, look for the cow sculpture (named Buttercup) outside the Agency of Agriculture which is quite cute!
Downtown is full of vintage shops and one of the only proper dive bars I found in Vermont.
Montpelier also calls itself the city of bridges as there are 10 bridges downtown. Depending on where you stand you can get beautiful photos with several of these bridges.
If you are looking for somewhere to stay, the Montpelier Inn is a 200-year-old building (which is ideal if you like traditional New England vibes) and it had the comfiest bed of my whole trip.
3. Woodstock
📍 Highlights: the Middle Covered Bridge, Billings Farm and Museum, Marsh-Billings-Rockefeller National Historical Park, Quechee Gorge
Woodstock is considered as one of “the prettiest small town in America,” and it earns it.
When you get there, try to park on Central Street as it’s the most practical.
If it’s too busy, then the Green is a good option and only a short walk away.
The shops are wonderful. I loved Elevation clothing, Unicorn and the Yankee Bookshop. They had beautiful children’s books about Vermont by local authors which I thought would make for a great gift.
It’s also a perfect creemee stop. This is actually where I got my first one from! Woodstock Scoops is located on Central Street and serves delicious creemee.
I took the one with the maple sprinkles and the waffle cones (worth the extra cost in my opinion!).
From Central Street it’s a two-minute walk to the Middle Covered Bridge, the most photographed in town.
For more history, Billings Farm and Museum (founded 1871) is a working dairy farm and one of the best outdoor history museums in the country.
While there, I would also recommend driving to Quechee Gorge, Vermont’s deepest gorge at around 165 feet.
You can go on a hike down to the Gorge there or simply admire the views from the bridge if you don’t fancy the walk.
On the way, you’ll also drive past the pretty red Taftsville covered bridge, one of the oldest in the state.
4. Bristol
📍 Highlights: Bristol Falls, Main Street shops, the village green and gazebo, Lord’s Prayer Rock
Bristol completely took me by surprise, and it ended up being one of the cutest little towns I saw on the whole trip!
It’s tiny, but it has this slightly western, frontier feel to it that I fell for straight away.
When you get there, park up, have a wander around the shops, then walk up to the gazebo on the green. The town band has actually played summer concerts there since the Civil War, which I thought was such a lovely touch.
The main street is full of great independent shops. I liked Snap’s, Out on Main and Emerald Rose, but my favorite was Island Girl jewelry, where I ended up buying a ring. It’s the kind of place where you can happily lose an hour just pottering about.
And if you’re visiting on a hot day, Bartlett Falls has a 14-foot waterfall, a swimming hole and even a rope swing. It’s a real local favorite.
Bristol isn’t on many itineraries, and honestly, that’s exactly why you should go.
5. Manchester
📍 Highlights: Hildene (the Lincoln family estate), the American Museum of Fly Fishing, the Manchester Designer Outlets, Northshire Bookstore
Manchester is bigger and more spread out than you’d expect, and it’s really two places in one.
There’s Manchester Village, the historic southern end with marble sidewalks and the grand Equinox resort, and then there’s Manchester Center, which is where all the cute shopping and eating is.
I’d start at the First Congregational Church. There’s free parking around the back, so you can hop out, take it in, and then drive over to the main street down in Manchester center.
Once you’re there, don’t miss the Northshire Bookstore. It was founded in 1976 and has been named the best independent bookshop on the East Coast, with over 300,000 titles and a lovely cafe inside. The Wood Store is also great for handmade wooden souvenirs at really fair prices.
Manchester is home to the Manchester Designer Outlets if you fancy a proper shop, and to Hildene, the 412-acre summer estate built in 1905 by Abraham Lincoln’s son, Robert Todd Lincoln.
It has formal gardens, walking trails and farm animals. Give it half a day if you can.
6. Grafton
📍 Highlights: the Grafton Inn, Grafton Village Cheese, the covered bridge, the Grafton Village Store
Grafton is a tiny, almost storybook village, and it became one of my favorites just for how peaceful and perfectly preserved it feels.
Much of it was carefully restored by the Windham Foundation, which is why it looks so pristine.
Go to the Grafton Village Store, which is full of local produce, food and souvenirs.
The real star of the village is the Grafton Inn. It dates back to 1801 and is one of the oldest continuously operating inns in the country. With its porch and white-washed brick, it was my favorite building of the whole trip.
The town is known for Grafton Village Cheese, made here since 1892, and there’s a sweet little covered bridge right by the cheese shop.
It’s a pedestrian one, so you walk in and look out at the river through the windows, which is honestly a much nicer way to enjoy a covered bridge than just driving through.
One practical note: there’s almost no cell signal in Grafton, so download your map before you arrive!
7. Middlebury
📍 Highlights: Otter Creek Falls, the UVM Morgan Horse Farm, the Henry Sheldon Museum, Middlebury College, Edgewater Gallery
Middlebury is a little bigger and built around Middlebury College, the prestigious liberal arts school founded all the way back in 1800, which gives the whole town a lovely energy.
Here’s a small tip that makes a real difference: walk up Main Street toward the church. The view up the street with the church behind is so much prettier than the other way around.
If you like animals, the UVM Morgan Horse Farm is just a few minutes away in nearby Weybridge. The Morgan is Vermont’s state animal, and this working farm is home to around 40 of them, all descended from a herd saved from extinction by Joseph Battell back in 1878.
And if you fancy stretching your legs, the Trail Around Middlebury is a 16-mile footpath that loops the whole town, with sections gentle enough for a casual stroll along the creek.
8. Waterbury
📍 Highlights: the Ben and Jerry’s factory, Cold Hollow Cider Mill, Vermont Artisan Coffee
Waterbury doesn’t have a compact, walkable downtown like the others, so think of it as the town you stop in for the attractions. And what attractions they are!
Top of the list, and honestly one of the highlights of my whole trip, is the Ben and Jerry’s factory. The company started in a renovated Burlington gas station back in 1978, and the factory tour here is only $6 for about half an hour. You get a short film, a walk along the production line, a bit of cookie dough, and a taste of the flavor of the day.
Don’t miss the Flavor Graveyard outside either, where discontinued flavors are “buried” with their own little headstones!
Just up the road, Cold Hollow Cider Mill makes one of Vermont’s most famous ciders, and its apple cider donuts are worth the stop on their own.
In the fall, the hot mulled cider here is unbeatable, and there’s a cute outdoor area with cornhole.
In summer you can get a creemee with a donut or an ice cream sandwich with a donut and creemee known as a ‘dreemee’.
And if you need a caffeine hit, Vermont Artisan Coffee has seriously good coffee and a giant coffee silo out front, which you really don’t see every day.
9. Brattleboro
📍 Highlights: the Latchis Theatre, the Brattleboro Museum and Art Center, the Retreat Tower
If you’re coming up from the south, Brattleboro is the artsy gateway to Vermont and well worth a stop.
It has a bit more of an industrial edge than the other towns, with handsome brick buildings, a long creative and slightly hippie streak, and an impressive number of churches packed onto Main Street.
It’s a brilliant town for a browse. I found a wonderful vintage shop and walked out with a stunning red vintage dress, and the Duchess Coffee Shop is a lovely spot that doubles as a bookshop.
Don’t miss the Latchis Theatre either. It’s a gorgeous 1938 Art Deco cinema built by a Greek immigrant, with zodiac symbols painted across a deep blue ceiling.
And if you happen to be around on the first Friday of the month, the town’s Gallery Walk fills downtown with art and music.
10. Waitsfield
📍 Highlights: the Waitsfield Covered Bridge, the Artisan’s Gallery, the Lareau swim hole, the Warren Store, Sugarbush and Mad River Glen
Waitsfield sits in the Mad River Valley, one of the prettiest stretches of Route 100, and it’s a classic Vermont village that’s well worth building into any road trip.
Its centerpiece is the Waitsfield Covered Bridge, built in 1833 and the oldest operating covered bridge in the state. It spans the Mad River right on Bridge Street, in the center of the village.
The village has a strong arts scene, including the Artisan’s Gallery, which represents more than 150 Vermont artists. There are some lovely coffee and food spots too, like Twisted Halo, which is known for its donuts.
On a hot day, the Lareau swim hole on Route 100 is a beloved local spot, with a rope swing and a little gravel beach on the river.
A few minutes down the road in Warren, the Warren Store has been the town’s general store since 1839, with a deli, a bottle shop and picnic tables.
And in winter, this whole valley becomes a real skiing hub thanks to Sugarbush and Mad River Glen.
So which town should you choose?
Honestly? If you can, do them all.
That’s the beauty of Vermont, the towns sit close together and the drives between them (especially Route 100) are half the fun.
But if I had to send my best friend to just a few, I’d pick Stowe for the iconic views, Montpelier for the underrated charm, and Woodstock for the classic Vermont postcard.
Then grab a maple creemee and thank me later.
Wherever you go, take your time, get off the main roads now and then, and keep an eye out for those covered bridges. Vermont rewards the people who slow down.
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