20 Of the cutest small towns in New England worth visiting!
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The region of New England is known for its Autumnal colors and enchanting small towns, which look like storybook pages come to life. Nestled below a canopy of golds and reds, clapboard houses lean into the wind, medieval steeples pierce the sky, and the locals sit on porches made with weathered shingles.
As you walk down cobblestone streets, the smell of warm chowder fills the air, and red barns and covered bridges appear in the distance.
If you ever wanted to experience the true, rural side of the USA, then small towns in New England offer a scene that you won’t find anywhere else in the U.S.
But since New England spans across seven states and 186,447 square kilometers, we’ve narrowed down the best coastal gems, mountain towns, and charming spots, so you can witness the New England charm for yourself.
The Best Small Towns In New England1. Plymouth, Massachusetts2. Burlington, Vermont3. Bar Harbor, Maine4. Merrimack, New Hampshire5. Camden, Maine6. Chatham, Massachusetts7. Greenwich, Connecticut8. Jamestown, Rhode Island9. Rutland, Vermont10. Groton, Connecticut11. Stockbridge, Massachusetts12. Stowe, Vermont13. Essex, Connecticut14. Oak Bluffs, Massachusetts15. Portsmouth, New HampshireMore New England Travel TipsTours of New EnglandPin to Save on Pinterest
1. Plymouth, Massachusetts
Plymouth is considered the birthplace of America’s pilgrim story and offers a glimpse into the country’s early beginnings.
|t’s a coastal town protected by Cape Cod Bay, and has many iconic landmarks telling the 17th century story of America’s first settlers, such as the Mayflower II and Plymouth Rock, which is where the pilgrims first set foot on American soil, and the Plimoth Patuxet Museums, which is a recreated village of the original 17th century village.
At this living museum, you can interact with actors dressed as the pilgrims and the Wampanoag tribe. It’s also kid-friendly, and the children will love the immersive experience.
Plymouth Rock is not worth it. It’s a rock with “1620” carved into it from when the pilgrims first came to the coast. A walk along the 3-mile Plymouth Long Beach is worth it though, especially during sunrise as you can watch the sun come up over the glassy waters.
History buffs can delve deeper into the past at the Pilgrim Hall Museum, the oldest public museum in the USA and home to an impressive collection of artifacts and exhibits.
Additionally, don’t miss the Plimoth Grist Mill, a living piece of history that showcases the town’s milling traditions.
If you haven’t figured it out already, Plymouth is all about history, but it’s also quaint and idyllic, with independent shops and art galleries, and restaurants serving local seafood pulled from the coast of Cape Cod that day.
2. Burlington, Vermont
If you want to move away from the coast, the New England small town of Burlington in Northwestern Vermont is one of the best places to visit, especially in the Fall or Winter.
Located on the banks of Lake Champlain, it isn’t really near any major highway systems like I-95, making it feel more remote and peaceful. Its off-the-beaten-track location makes it one of the best towns to visit to escape the crowds on a New England road trip.
Steeped in heritage, Burlington flourished as a bustling lumber and manufacturing center in the 19th century, leaving behind a legacy of industrial grandeur.
The vibrant waterfront was once the third largest lumber port in the country during the mid-1800s, but now, from the waterfront park, you can enjoy the mystique of Lake Champlain (the eighth largest naturally occurring body of fresh water in the USA), which has its own monster folklore similar to Scotland’s Loch Ness, though the Champlain monster is referred to as Champ or Champy.
It is also home to other weird things like the world’s tallest filing cabinet – this small town has tons to enjoy.
Immerse yourself in Burlington’s past at the Pilgrim Hall Museum, which showcases artifacts from the Revolutionary War era, and war history enthusiasts shouldn’t miss a visit to Battery Park, a historic site that served as a defensive position during the War of 1812.
3. Bar Harbor, Maine
If you really want to find the cutest towns in New England, you have to see the small island of Mount Desert Island in Maine, known for its gorgeous beaches, mountain peaks, and and the pristine beauty of Acadia National Park.
The most well-known small town on the island is Bar Harbor, which was once known as Eden, and was transformed into a popular summer resort destination in the early 20th century.
Explore historic sites like the Bar Harbor Historical Society and the iconic Bar Harbor Inn, or take a scenic drive along the picturesque Park Loop Road in Acadia National Park.
Animal lovers will enjoy taking a whale-watching excursion, which offers a chance to see migrating whales off the coastline.
There are carriage rides to enjoy at all times of the year, too, and you can learn things you never knew about the Rockefellers! Yep, Bar Harbor is known for once being a tourist attraction for millionaires and celebrities, and many famous people have homes here.
With its breathtaking natural beauty, Bar Harbor is not to be missed. Don’t miss out on a chance to try the famous seafood of the area, especially lobster rolls.
4. Merrimack, New Hampshire
If you’re planning a romantic getaway, then you have to consider the small town of Merrimack, simply because of all of the breweries (both beer and wine) in the surrounding areas.
Nestled in the heart of Hillsborough County, Merrimack is a hidden gem waiting to be discovered.
Originally inhabited by the Penacook Indians, this town has deep roots in Native American culture.
Go and see the Merrimack Historical Society to learn about the fascinating heritage of the region, or explore the scenic beauty of the Merrimack River, where you can go fishing or boating.
Don’t miss the opportunity to hike along the picturesque trails of Horse Hill Nature Preserve, which provides breathtaking views of the surrounding landscape.
Seeing the Fall foliage change color is truly spectacular along the several trails you can hike here.
5. Camden, Maine
One of the not-so-famous New England vacation spots is Camden Hills State Park.
Nestled in the scenic Mid-Coast region of Maine, Camden is an old and historic town with plenty to offer.
Settled in 1769, this charming New England town derived its name from the first Earl of Camden, Charles Pratt, who played a significant role in American history.
You can learn about the town’s past by visiting the Camden-Rockport Historical Society and exploring exhibits that showcase the everyday life of Maine families in the 18th and 19th centuries.
On top of Mount Battie, you can see Camden and all of Penobscot Bay. The small town also has harbor cruises and whale watching tours during the appropriate times of the year. Don’t miss the opportunity to experience the thrill of sailing aboard a schooner, capturing the spirit of Camden’s maritime heritage.
Skiers and snowboarders will find the Snow Bowl Ski Resort in winter to be the perfect place to carve up some powder.
6. Chatham, Massachusetts
This cute beach town on the southeast corner of Cape Cod can’t be missed during your New England trip.
Dating back to 1606, when Samuel de Champlain first explored the area, Chatham is steeped in Native American heritage and European influence.
Take a stroll along picturesque beaches like Lighthouse Beach or explore the charming streets lined with quaint boutiques and shops.
Don’t miss the opportunity to visit Chatham Lighthouse, offering stunning Atlantic Ocean views.
From pristine beaches to beautiful and historical lighthouses with amazing views, it’s the place to be.
If you’re into railroads, don’t forget to visit the Chatham Railroad Museum.
7. Greenwich, Connecticut
From boating in Long Island Sound and seeing old colonial-style homes mixed in with Gilded Age mansions, Greenwich has it all. And it’s possible to visit on a day trip from New York City.
With its rich historical roots dating back to 1640, this charming town has captivating stories to tell. From its early settlement by Dutch settlers to its role as a border town between New Netherland and New England, Greenwich is steeped in intriguing history.
But it’s not just the past that makes Greenwich a must-visit destination. The town boasts an array of attractions, including the stunning Greenwich Point Park, the captivating Bruce Museum, and the enchanting Putnam Cottage.
A famous New England attraction is Great Captain Island, which is a quick ferry ride away.
8. Jamestown, Rhode Island
With lighthouses, beaches, and forts, Jamestown, Rhode Island is another cute small town with a lot of maritime history and picturesque landscapes.
Visit the Beavertail Lighthouse and Park, Fort Wetherill State Park, and the Jamestown Windmill to learn about the town’s past, or take a stroll along the Claiborne Pell Newport Bridge and soak in the breathtaking views.
Don’t miss Fort Adams State Park, 25 minutes away over the river in Newport, where there’s swimming, sailing, and festivals to enjoy at different times of the year.
Also, visit Castle Hill Lighthouse, which is technically on Newport Island, which is right next to Jamestown. The downtown area in Jamestown is also really pretty and a nice place to wander around.
9. Rutland, Vermont
From hikes to children’s museums to 19th-century castles, what more could you want from the beautiful New England small town of Rutland?
Nestled in the picturesque state of Vermont, Rutland holds a storied past. It was established in 1761 and was once the capital of Vermont and an influential point in the region’s transportation and manufacturing sectors.
Marvel at the architectural beauty of the West Rutland Academy, built in 1810, or discover the remnants of Rutland’s marble industry, which once thrived in the area.
10. Groton and Mystic, Connecticut
One of the best New England attractions has to be the Navy submarines in Groton. It’s also only a 15-minute drive away from Mystic, which is another small town, but the attractions blend with Groton so it’s worth visiting them both in one trip. The town of Mystic became famous after it appeared in the Julia Roberts movie, Mystic Pizza.
All things aquatic are to be seen here, from the Mystic Aquarium to their submarine museum and an old whaling ship that’s now out of commission.
Groton was founded in 1646 as part of New London, and the early European settlers used its position for shipbuilding and submarine production.
The Mystic Seaport Museum on the banks of the Mystic River is a great place where you can explore maritime history, or you can visit the Submarine Force Library and Museum to learn about the legacy of the Navy’s submarines.
11. Stockbridge, Massachusetts
Credit: Deposit Photos
Nestled in the heart of Massachusetts in the iconic destination known as The Berkshires, Stockbridge is a charming town that was originally settled as a Christian mission known as Indian Town.
Take a stroll along Main Street and admire the historic architecture or visit the Mission House, a remnant of early missionary efforts towards the local Mohican tribe.
If you’re a fan of Norman Rockwell, visit his museum while you’re there, too.
12. Stowe, Vermont
Stowe is another town in Vermont that beckons visitors with its rich history, but it also attracts people for another reason.
The iconic Stowe Mountain Resort, famous for its world-class skiing and breathtaking white mountain views, is the place to be if you’re looking for New England towns for the winter.
In the summer and Autumn, explore the scenic hiking and biking trails of Mount Mansfield or take a calming stroll along the stunning Waterbury Reservoir, or bike the sublime Stowe Recreation Path.
With its blend of history and natural beauty, Stowe is the place to be. We particularly love it in Autumn when the foliage comes alive with color. It’s places like Stowe that give New England the reputation for being the best destination in the USA for Fall.
13. Essex, Connecticut
Credit: Deposit Photos
Nestled along the picturesque Connecticut River, Essex, originally named Potapoug Point, was once a thriving port town and hub of shipbuilding, but is now a sleepy and quaint town that beckons you to slow down a pace.
Stroll along the old New England Main Street, lined with historic homes that harken back to Essex’s shipbuilding heyday, or discover the remnants of the Battle of Essex at the British landing site.
14. Oak Bluffs, Massachusetts
Nestled on the enchanting Martha’s Vineyard, Oak Bluffs, originally part of Edgartown and bordering Nantucket Sound, is one of the most exciting towns in New England.
The town is said to be home to no more than 5,341 residents, but it booms in the summer as many people take up summer residence here.
Take a stroll through the picturesque streets lined with historic gingerbread cottages, or visit the Oak Bluffs Historical Commission to delve deeper into the town’s architectural heritage.
Don’t forget to enjoy the stunning beaches and visit the Flying Horse Carousel, the oldest operating platform carousel in the USA!
15. Portsmouth, New Hampshire
Nestled on the scenic seacoast of New Hampshire, Portsmouth is another major shipbuilding center and fishing community that’s worthy of exploration.
See notable sites such as Strawberry Banke, which offer a glimpse into Portsmouth’s colonial heritage, stroll through the picturesque streets lined with historic architecture, or visit the Portsmouth Harbor Lighthouse for stunning views.
16. Newburyport, Maine
Newburyport in Maine is a quintessential New England coastal town with a lively downtown area, where red-brick streets are lined with boutiques, art galleries, and cafés.
The working waterfront offers scenic boardwalks and opportunities for whale-watching cruises, while nearby Plum Island is where to go for walks on sandy beaches, birdwatching at the Parker River National Wildlife Refuge, and a chance to escape into nature.
Like most coastal towns on the East Coast, Newburyport has a maritime history that you can learn about in the Custom House Maritime Museum, which dives into the city’s seafaring past.
17. Provincetown, Massachusetts
Looking across the bay from Plymouth, you just might be able to make out Provincetown, which sits at the very tip of Cape Cod.
This town is a kaleidoscope of color and character, humming with creative energy. It has galleries and studios spilling with art, and a lively main street, Commercial Street, which is full of cozy cafés, quirky shops, and refreshing sea salt air.
Nearby are pristine beaches and the windswept dunes of the Cape Cod National Seashore to Race Point, where whales breach on the horizon.
Provincetown is both historic and bohemian, and totally unique from other towns in New England.
18. Woodstock, Vermont
Ahh Woodstock, you may have heard the name before as Woodstock Live Music Festival, but that’s not the Woodstock in Vermont. That festival takes place in New York State. But Woodstock, VT does have its own arts festival with live music!
The town of Woodstock is one of our favorite towns in Vermont. It’s another quaint small town with an old-world charm. You’ll find many boutique stores, cozy coffee shops, and live music on weekends (and yes, some festivals too).
Another reason to visit Woodstock is to visit the Quechee Gorge, the deepest gorge in Vermont. It’s said the gorge was formed by glaciers over 13,000 years ago and is still deepening thanks to the constant stream of the Ottauquechee River that cuts through 165 feet below.
19. North Conway, New Hampshire
North Conway, nestled in the heart of the White Mountains, is a small village is known for its natural beauty. It’s the gateway to Echo Lake State Park, Cranmore Mountain Resort (which is famous for its skiing in the winter, and hiking in the summer), as well as Diana’s Baths, a refreshing natural swimming pool and waterfall.
It’s also known for its railway history, which began in the 19th century. The railroad boosted the town’s popularity and turned it into a resort area, where people would flock from all over the US to take in the breathtaking scenery. You can see the remains of this railway history at the Conway Scenic Railroad, a historic train depot with vintage trains.
It’s also located at the foot of Mount Washington, the highest peak in the Northeast, and a gateway to the White Mountain National Forest. So if you love hiking, you’re not short of trails to choose from here.
Ready for a nearby adventure? How To Bike the Franconia Notch Recreation Path, NH
20. Bristol, Rhode Island
Bristol is a small town in Rhode Island that sits on the Thames River – it feels as much like England as you can get without actually visiting (after all, the river is named after the same famous one that winds through London).
Although named after a British city, this is very much small-town America at its core. It feels like the whole town is painted in red, white, and blue.
It’s known for hosting the nation’s oldest Fourth of July parade, and the town, although small, wears its history and patriotism proudly, with flag-lined streets and centuries-old homes with flags draping from the windows.
Wander along the waterfront and watch the sailboats drift past, or walk around the manicured Blithewold Mansion and Gardens.
If you like to get active on vacation, take a bike ride along the East Bay Bike Path and around Independence Park.
Map of Small Towns in New England
Best time to visit New England
The best time to visit New England is in the Fall, without a doubt. These seven states come alive this time of year, with the dense foliage awash in colors of red, yellow, and orange.
It’s one of the most famous places to visit for Fall colors in the world, so naturally time your visit for late September and October to see colors.
It’s also a great place to visit in summer months for a bit more peace and quiet. Most people flock to destinations like Florida or California for their summer vacation, which means the New England states, particularly those away from the coast, get less summer traffic.
Summer visitors will find fewer crowds in early June, but they will pick up from July and August.
More New England Travel Tips
Need more inspiration for your trip to New England? Here are some other helpful guides…
Tours of New England
Activities in Boston with Get Your Guide:
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