The 15 Best Small Towns In New England You Must Visit!

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The enchanting region of New England is known for its idyllic and charming atmosphere. The best way to experience the charm of this land is to visit the small towns of New England.

Wandering around these small towns is like opening a time capsule. These idyllic places are a far-cry from the bustling cities, filled with quaint streets lined with historic colonial architecture, with smiling, welcoming communities standing on their porches.

New England’s small towns exude a sense of timeless charm and a delightful escape from the ordinary.

But if you’re not sure what are the most charming towns to visit in New England, here are some of our favorites that you cannot miss.

The Best Small Towns In New England

New England is in the northeast of the United States and includes Maine, New Hampshire, Vermont, Massachusetts, Rhode Island, and Connecticut. If in need of a hire car in New England, check rental rates and availability here

The following towns are spread far and wide in the region.

1. Plymouth, Massachusetts

stone wall with wooden doors

Plymouth is considered the birthplace of America’s pilgrim story and offers a glimpse into the country’s early beginnings.

|conic landmarks such as the Mayflower II and Plymouth Rock tell of the towns history, where the pilgrims first set foot on American soil.

Plymouth Rock is not worth it. It’s a rock with “1620” carved into it from when the pilgrims first came to the coast.

What is worth it? Plimouth Plantation where 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.

Delve deeper into the past at the Pilgrim Hall Museum, 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.

2. Burlington, Vermont

A lit up city at night

One of the best New England small towns is Burlington, which isn’t really near any major highway systems like I-95, making it feel more remote and peaceful. It’s a perfect off the beaten track New England road trip destination for that reason.

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 Lake Champlain and 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.

Don’t miss Battery Park, a historic site that served as a defensive position during the War of 1812.

3. Bar Harbor, Maine

water surrounded by mountains

If you really want a full weekend getaway in New England, you have to see the small island of Mount Desert Island in Maine.

The small town on the island is Bar Harbor, which was once known as Eden, that 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.

Animals 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!

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

road lined with trees

If you’re planning a romantic getaway in New England, then you have to include the small town of Merrimack, simply because of all of the breweries (both beer and wine) in the area.

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

A sunset over a body of water

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.

You can also visit Snow Bowl Ski Resort in winter for some excellent skiing.

6. Chatham, Massachusetts

lighthouse on the beach

This cute beach town on the south east 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

lighthouse on rocks in the water

From boating in Long Island Sound and seeing old colonial style homes mixed in with gilded-age mansions, Greenwich has it all.

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.

Located an hour from New York City, it makes for a great place to start a New England getaway.

A famous New England attraction is Great Captain Island, which is a quick ferry ride away.

8. Jamestown, Rhode Island

large deck on historic home looking at ocean

With lighthouses, beaches, and forts, Jamestown, Rhode Island, has it all.

With its rich maritime heritage and picturesque landscapes, Jamestown has so much to do.

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

bridge over water

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, Connecticut

submarine in water

One of the best New England attractions has to be the Navy submarines in Groton.

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 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.

Groton is also close to the town of Mystic, which became famous after it appeared in the Julia Roberts movie, Mystic Pizza.

11. Stockbridge, Massachusetts

Deserted Alley Lined with Traditional Gift Shops Decorated for Halloween
Credit: Deposit Photos

Nestled in the heart of Massachusetts in the iconic destination known as The Berkshire, 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

fall foliage and church steeple Stowe  View from Sunset Rock

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, explore the scenic hiking and biking trails of Mount Mansfield or take a calming stroll along the stunning Waterbury Reservoir.

With its blend of history and natural beauty, Stowe is the place to be.

13. Essex, Connecticut

Waterside Houses with Boats Moored to Wooden Jetties on a Clera Autumn Day. Connecticut River, Essx, CT.
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

Shingled mansions along East Chop Road in Oaks Bluff, Martha's Vineyard

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! Read our post on things to do in Martha’s Vineyard.

15. Portsmouth, New Hampshire

strawberry banke museumin 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.

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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9 thoughts on “The 15 Best Small Towns In New England You Must Visit!”

  1. Thank you so much for all of the information on the great small towns of New England. My family loves Boston, but have never ventured out to any of the small towns in the area. I’m looking forward to taking a road trip to see the fall colors soon, and now have several cool looking towns to add to our list of activities! My son will especially love Groton and Rutland. Thanks for all of the inspiration!

    1. Hey Christy, glad you found this post about things to do in New England helpful. We loved our trip to Boston too, and the New England area in general.

  2. Wow, trip down memory lane! When I was a university student here in The Netherlands I did an internship with a company in Lexington, MA and lived in Cambridge, MA for 6 months. I absolutely loved the area! Boston is a fantastic city, but I also went for lots of weekend trips up north to New Hampshire for hiking. I’m sure lots has changed since then, but it’s great to see so many familiar names on this list 🙂

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