11 Of The Most Captivating Small Towns In New England
New England is a group of states in the northeastern corner of the country consisting of Maine, Vermont, New Hampshire, Connecticut, and Massachusetts. With towns and landscapes ranging from rugged and coastal to opulent and colonial, it can be daunting to narrow it down to just a few destinations worth exploring. Portsmouth offers culinary treats and Newport teases with glimpses of the Gilded Age, while Nantucket, Provincetown, and Block Island sit far removed from it all in a world of their own. These eleven towns have just the right blend of natural splendor, charming community, and comfort, and are a great place to start when planning your next trip to New England.
Kennebunkport, Maine
This coastal charmer offers plenty of opportunities for rest and relaxation. Resort town Kennebunkport and neighboring Kennebunk offer easy access to the water with their many pristine beaches, such as Mother’s Beach, Colony Beach, and Parsons Beach, all of which are gorgeous places to relax and lose yourself to the restful sound of waves. If you want something more rugged, the Kennebunk and Musseum Rivers wind through beautiful hills and offer a more adventurous time. Aquatic attractions abound in and around the area, from sea kayaking and white water rafting to whale watching.
Those wanting to enjoy the vibes of this coastal town without getting their feet wet can find plenty to keep them entertained on dry land. The Waterhouse Center offers iconic ice skating in winter and serves as a hub for the town year-round, hosting farmers' markets and other community events, while The Boathouse offers riverside dining.
Bennington, Vermont
Standing tall along the Appalachian Trail, Bennington, Vermont has a history both unique and interwoven with that of America. The site of one of the earliest victories of the Patriots, Bennington was also the home of Ethan Allen, the charismatic leader of the Green Mountain Boys, a volunteer militia that had a pivotal role in the American Revolution. This nuanced historical period lives on in Bennington, where reenactments of the Battle of Bennington have occurred annually for almost 250 years.
Visitors can explore this rich revolutionary history both at the Bennington Battle Monument and the Bennington Museum. And the historical connections do not end there. The Robert Frost Stone House Museum, where the famous poet lived from 1920 to 1929 and where he wrote many of his most popular poems, such as “Fire and Ice” and "Nothing Gold Can Stay," is situated only a few miles from Frost’s grave. And as a site along the Appalachian Trail, Bennington offers easy access to gorgeous mountain hikes.
Nantucket, Massachusetts
“The Faraway Land” is a perfect name for this charming conservation capital whose beaches have captivated tourists for decades. Sitting on an island just 30 miles off Cape Cod, a large portion of Nantucket is devoted to conservation, with many pleasant beaches. Once such slice of paradise is Stone’s Beach, which not only boasts pristine dunes, a temperate surf, and some nice greenery, but also a free library and plenty of benches to sit and read or simply relax. To the west, Madaket Beach is famous for its gorgeous sunsets and soft sand. Finally, in the north, Steps Beach offers a gentle surf with a sandbar and, in summer, a chance to see bioluminescent sea life. When it's time to head inside, The Nautilus serves fresh seafood and custom cocktails to toast your day's adventure.
Camden, Maine
Some small towns switch between sleepy and stellar as the seasons change, but Camden, Maine, captivates all year round. March’s Maine Restaurant Week, which celebrates the many eateries in the heart of New England, is the perfect opportunity to try a lobster roll at Camden Deli. During the summer, visitors can participate in one of Maine’s oldest events, the Camden Garden Club House & Garden Tour, which has been going for over 70 years.
Autumn in New England is never to be missed, but Camden adds a maritime menagerie to the mix with the Camden Windjammer Festival, where you can stroll the harbor and watch schooners sail into port. And in winter, Camden’s Snowbowl opens for skiing and snowboarding and hosts the annual US National Toboggan Championships every February. And of course, the town of Camden has its own timeless charm, including local shops, dining options, and fun attractions all year long.
Mystic, Connecticut
Magic is in the name with Mystic, Connecticut. Just north of town, Maugle Sierra Vineyards offers tastings and hosts live music on weekends. The Mystic Aquarium offers plenty of fun and excitement, with thousands of marine animals. From virtual painting with beluga whales to checking out northern fur seal pups, the aquarium not only offers a unique experience but also works to ensure the conservation of these animals.
To add a dash of silver-screen magic to your trip, Mystic Pizza, which inspired the 1988 movie by the same name, serves up slices of heaven (or at least pepperoni). If seafood is on the menu, the award-winning Shipwright’s Daughter brings sustainability to the table with a locally-sourced seafood menu and a commitment to investing in their community.
Portsmouth, New Hampshire
Portsmouth, New Hampshire, ranks among the most captivating culinary experiences in New England. Options abound, regardless of whether you want a savory feast or a sweet treat. If you’re jonesing for a cup of joe, or even something a bit stronger, Cup of Joe Café and Bar delivers plenty of both, even at the same time with one of their famous espresso martinis. For a nice lunch or casual dinner, the Portsmouth Gas Light Company offers a multi-floor experience, with a pizza pub, a grill, and a third-floor nightclub for whatever your heart desires.
As for upscale dining, The Library Restaurant is a steakhouse in the historic Rockingham Hotel, which has hosted seven presidents. They offer unique services for special occasions, such as gift baskets and custom floral arrangements. And for sweets or desserts, Fezziwig's Food and Fountain in Pickwick's Mercantile delights with a full espresso bar, soda fountain, and all manner of crepes and pastries.
Bristol, Rhode Island
With seven museums, Bristol offers a deep look at the past and enough to keep even the most ardent history buff engaged. Celebrating its 250th birthday in 2026 and with one of the oldest July 4th celebrations in the US, Bristol puts its history front and center for visitors and residents alike. Originally a summer estate built in the early twentieth century, Blithewold's almost fifty rooms and gardens offer an impeccably preserved example of a country getaway of that era.
Mount Hope Farm also offers garden tours and accommodations on a historic estate, while the Herreshoff Maritime Museum consists of not only the Herreshoff family’s home and offices, but a large marina with more than seventy boats built by the Herreshoff Manufacturing Company. For a different historical perspective, the Bristol Historical and Preservation Society is based out of an abandoned jail built from large granite blocks reportedly used as ballasts for sailing ships. Here, you can browse the library's extensive collection of genealogical materials, ships' diaries, photographs, and public records.
Newport, Rhode Island
If you’re looking to live it up like the well-to-do of the 1920s, storied Newport offers just the thing. Once a playground of the wealthy who flocked to the coast to escape the summer doldrums, many of the mansions in Newport were used as filming locations for HBO’s The Gilded Age. These captivating glimpses into history are more than sets and backdrops, however. Visitors can tour many iconic mansions, such as The Breakers, of Vanderbilt fame, and Rosecliff, yet another shooting location, this time for the film adaptation of The Great Gatsby. You can even enjoy a picnic on the lawns, so bring a blanket, some champagne, and your copy of the classic novel.
If that isn’t enough of the high life, many of the private gardens, such as The Blue Garden, are open to the public and give visitors a stunning retreat, while the International Tennis Hall of Fame is located in the historic Newport Casino. And for those who want to pretend, just for a moment, that they’re back in the Roaring Twenties, Newport’s Jaguar Tours offer visitors a taste. Book the Scandalous Newport Tour to hear all the salacious details from behind the closed doors of Rhode Island's rich and infamous.
Provincetown, Massachusetts
In Provincetown, individualism and artistic expression are key. Perched on the most extreme tip of Cape Cod, more than sixty miles from the mainland, Provincetown is a haven for everyone and is particularly popular with LGBTQ+ visitors. An artists’ colony for over a century, Provincetown has countless galleries where you can take in any medium that inspires you. The East End of town is known as the Gallery District for the many art galleries that fill it. The Bowersock Gallery holds a wide variety of pieces from multiple styles and genres, and is one of many spots along Commercial Street that make up the backbone of the Gallery District.
But Provincetown isn’t just an artist’s paradise; it strives to be inclusive and holds a variety of events all year round, such as Carnival, a weeklong summer festival with parades, costume contests, and live performances. For dining, there are several options, but the Lobster Pot is perhaps the most iconic. The popular spot is as much a landmark as it is an eatery, serving seafood and other local favorites for generations.
Block Island, Rhode Island
No matter where your interests lie, you can find an opportunity to explore and experience the natural world without going more than twelve miles off the coast of Rhode Island. With almost half of it dedicated to conservation, Block Island offers a refuge to species that have vanished from the rest of New England. For birdwatchers, Clay Head Trail and its “maze,” a tangle of unmarked trails that lets you wander as you wish, is an excellent place to see songbirds migrating in the fall.
If you’d rather saddle up with a trusty steed, Rustic Rides Farm offers lessons and tours for beginners and experienced riders alike. For even more of a rush, the DiamondBlue Surf Shop is centrally located and perfectly placed to help you catch a wave, and there’s plenty of pristine beaches to choose from on this coastal island paradise.
While it can be daunting picking just one of the many towns in New England, each and every one has something special and unique to make it worth visiting. Some embrace their history and put it front and center for their visitors to experience for themselves, while others invite you to breathe in the wonders of nature. Everyone’s priorities will differ when they’re building an itinerary to experience the wonders of New England, but with so many splendid small towns to explore, you really can’t go wrong, especially with these eleven jewels as a starting point.
