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Are you planning a trip to New England and looking for the prettiest small towns to add to your itinerary? You’ve come to the perfect place!
New England does small towns better than just about anywhere: white church steeples, village greens, harbors, covered bridges and cozy main streets… they really have it all!
And if you are a Gilmore Girls fan, you’re in for a treat!
Please note that these towns are beautiful all year round but summer and the fall are particularly good!
⛪ 1. Stowe, Vermont
Stowe is one of the most famous small towns in Vermont and for good reason: it’s everything you imagine Vermont will be.
As you get there, take some time to explore downtown. Main Street is home to some amazing old-fashioned stores.
You can also walk to the viewpoint to see the white Community Church against the mountains.
This is the most iconic view of Stowe and if you are visiting in the fall, it really is special! If you have more time, I would also recommend cycling the Stowe Recreation Path.
But that’s not all, Stowe also has a lot to offer outside of downtown.
Make sure to go to the von Trapp Family Lodge which is an Austrian style lodge built by the family from the Sound of Music.
You can also go to the Mountain resort where you can take the Gondola Skyride up to Mount Mansfield, Vermont’s highest mountain.
Finally, keep driving up Smugglers’ Notch. It’s one of the most scenic drives in New England all-year round but it’s absolutely magical in the fall.
⚓ 2. Mystic, Connecticut
Mystic is a lively little seaside town in Connecticut. It’s located on the Mystic River, right near the border with Rhode Island.
As you head downtown, you’ll get to the Bascule Bridge, a 1920s drawbridge that lifts to let boats through. Time it right and you can watch it go up.
From there, walk up Main Street where you’ll find independent shops, cafes and seafood spots.
Make sure to stop at Mystic Pizza, the pizzeria made famous by the Julia Roberts film.
You can also visit the Mystic Seaport Museum, the largest maritime museum in the country, and the Mystic Aquarium.
If you love a browse, Olde Mistick Village is a fun outdoor shopping spot full of quirky little stores.
📸 3. Woodstock, Vermont
Woodstock is regularly named one of the prettiest towns in America, and it lives up to it.
As you arrive, park near the green and take a walk around. You’ll find historic homes and the Middle Covered Bridge, which is one of the prettiest covered bridges in Vermont.
Head to Central Street where you’ll find independent shops, galleries and cafes.
Make sure to grab a maple creemee while you’re there, it’s a Vermont must!
If you have more time, visit the Billings Farm & Museum just outside the center. It’s a working farm and a great way to learn about Vermont’s rural history.
Woodstock is lovely year round but it’s especially beautiful in the fall.
🎓 4. Hanover, New Hampshire
Hanover is a classic New England college town, built around Dartmouth College.
The green sits right in the middle, surrounded by the Ivy League campus. Take some time to walk around and enjoy the setting.
From there, head to Main Street which is full of shops and cafes with a fun student buzz. Make sure to stop for a coffee and soak up the atmosphere.
It’s a relaxed, welcoming town and it’s at its best in the fall when the whole campus turns gold and red.
💫 5. New Canaan, Connecticut
New Canaan is one of the prettiest towns in Connecticut, and it’s an easy train ride from New York City.
It has an elegant main street lined with boutiques and cafes, and the houses are so cute they look like something from a film set.
Park near Elm Street and have a wander. There are lots of nice places to shop and eat.
If you love architecture, go and see the Glass House, a famous modernist home designed by Philip Johnson.
And if you’re a Gilmore Girls fan, this is exactly the kind of idyllic small town that will remind you of Stars Hollow!
🎭 6. Brattleboro, Vermont
Down in southern Vermont, Brattleboro is an artsy town with a creative, bohemian feel.
It’s a great place to slow down and browse. You’ll find vintage shops (I found some beautiful dresses there!), galleries and bookstores all around the walkable downtown.
If you have time, catch a film or a show at the Latchis Theatre. It’s a beautiful Art Deco cinema right in the center.
If you’re there on a Saturday, the farmers market is well worth a visit.
Just outside town, Retreat Farm has walking trails and farm animals, and there’s a pretty covered bridge nearby too.
🚤 7. Kennebunkport, Maine
Kennebunkport is a beautiful coastal town in southern Maine.
Start in Dock Square, the heart of town, where you’ll find shops, galleries and restaurants. From there, walk along the harbor and watch the boats come and go.
Make sure to drive along Ocean Avenue too. It takes you past beautiful summer homes and out to Walker’s Point, the Bush family compound, which you can see from the road.
And of course, this is Maine, so you have to try a lobster roll while you’re here!
⛵ 8. Milford, Connecticut
Milford is a laid-back coastal town on Long Island Sound, with one of the longest greens in Connecticut.
It has a pretty downtown that’s easy to walk around, with lots of independent shops to browse. There are also nice coffee shops and places to eat here.
I loved Café Atlantique for breakfast, their omelettes are so good!
I would also recommend heading down to Milford Landing Marina. It’s a lovely spot for a walk along the water.
Finally, make sure to visit Silver Sands State Park. At low tide, a sandbar appears and you can walk across to Charles Island. Just keep an eye on the tides as they come in fast!
🚣 9. Wickford Village, Rhode Island
Wickford Village is one of the prettiest little harbor villages in New England.
It has a walkable center full of independent shops, pottery studios and cafes, plus a lovely waterfront.
Take your time strolling the streets and looking at the historic colonial homes. There’s a self-guided Wickford Walk you can follow, with a map in the village.
Make sure to stop at Wickford Cheese & Sundry if you love cheese and deli treats.
It’s a peaceful spot and a great place to slow down for an afternoon.
🦞 10. Bar Harbor, Maine
Bar Harbor is the gateway to Acadia National Park, and a beautiful coastal town in its own right.
Spend some time downtown, where you’ll find shops, cafes and plenty of lobster shacks.
Make sure to walk the Shore Path for lovely ocean views. And at low tide, you can cross the sandbar out to Bar Island.
It’s also the perfect base for exploring Acadia. From here you can drive the Park Loop Road or head up Cadillac Mountain, which in winter is the first place in the US to see the sunrise.
🏝️ 11. Nantucket, Massachusetts
Nantucket is an island town about 30 miles off Cape Cod, and you get there by ferry, which is part of the fun.
It feels wonderfully preserved, with cobblestone streets, grey-shingled cottages and old whaling captains’ homes.
Spend time wandering the historic center. It’s full of independent shops and restaurants.
Make sure to explore the beaches too. You can rent a bike and cycle out to them at your own pace.
It has a relaxed, upscale island feel and it’s a lovely place to spend a day or 2.
🕯️ 12. Lubec, Maine
Right at the easternmost tip of the US, Lubec is a remote little town that most visitors never reach.
That’s exactly what makes it special. It’s quiet, wild and unspoiled.
Its highlight is the West Quoddy Head Lighthouse, with its candy-cane red and white stripes. It sits in a state park with dramatic coastal trails, so bring your walking shoes.
As it’s so far east, it’s also one of the first places in the country to see the sunrise, so it’s worth getting up early if you can.
It’s a real bucket-list spot for anyone who loves lighthouses and rugged coastline.
🧌 13. Charlestown, Rhode Island
Charlestown is a laid-back coastal town in Rhode Island.
For a small town, there are actually quite a lot of things you can do here.
First, head down to Charlestown Beach for some relaxing beach time. The drive along Charlestown Beach Road is lovely, with houses on stilts lining the way.
Make sure to stop at Dave’s Coffee just off Route 1. It’s one of my favorite coffee shops in New England and the garden at the back is amazing.
Don’t miss Ninigret Park either, where you can find the famous giant trolls. There are two of them and it’s an easy walk around the lake to see them.
🗺️ Map of these New England Small Towns
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