Aerial view of fall colors in Chester, Vermont.

6 Underappreciated Towns to Visit in New England

You may think you know New England, but think again. There is a lot of ground to cover in the six states of Maine, Vermont, Massachusetts, Rhode Island, Connecticut, and New Hampshire, making it easy to overlook the region’s hidden gems. Have you ever hiked a mountain in the middle of a lake, visited a UFO monument, or gone on a moose safari? Get away from the crowds and off the beaten track to experience these undiscovered delights and more. New England is full of hidden treasures…if you know where to look.

Barkhamsted, Connecticut

Saville Dam with colorful trees covering hills in the background, Barkhamsted, Connecticut.
Saville Dam with colorful trees covering hills in the background, Barkhamsted, Connecticut.

In the green rolling hills of Litchfield County, on the shores of Farmington River, you’ll find the pretty hamlet of Barkhamsted. This quaint country town is a favorite with hikers and outdoor adventurers thanks to its picturesque location near the Enders State Forest and the Barkhamsted Reservoir. The former is a 1,500-acre woodland with several scenic trails that meander through the forest and by the park’s stunning waterfalls. The Reservoir offers more breathtaking views.

This is where you’ll find the Saville Dam, a local landmark that looks more like a medieval outpost than a pump station. The stone turret overlooks the grassy banks and glassy calm waters of the dam, making it the perfect picnic spot on a sunny day. The reservoir is fed by nearby Lake McDonagh, a gorgeous public recreation area with fishing, boating, swimming, and hiking facilities. After all that action, unwind in the evening at the Pleasant Valley Drive-In Theater, a blast from the past where you can watch movies under the stars.

Greenville, Maine

Close-up of a seaplane on Moosehead Lake, Greenville, Maine.
Close-up of a seaplane on Moosehead Lake, Greenville, Maine.

Known as the gateway to Maine’s north country, Greenville is a scenic town at the lower end of Moosehead Lake, the state’s largest body of freshwater. Lily Bay State Park is a great starting point for exploring the lake, with beautiful waterfront trails and quiet swimming spots. For a truly unique experience, take a boat out to Mount Kineo, an unusual geological formation in the middle of the lake boasting 800 ft cliffs. A viewing platform at the top gives stunning 360-degree views of the lake.

As you’d guess from the name, the Moosehead Lake area is one of the best places to spot a moose. Take a moose safari for a guaranteed sighting, or take your chances yourself by hiking one of many trails in the Maine Highlands. Back in town, explore Greenville’s rich history at the Moosehead Cultural Heritage Center, a historic building downtown that houses an aviation museum and a ‘Moosehead Memories’ exhibit.

Sheffield, Massachusetts

Sheffield, Massachusetts: A village in Berkshire County situated in the Berkshires hills.
Sheffield, Massachusetts. Editorial credit: Richard Cavalleri /

Pastoral and idyllic, Sheffield is where to come when you want to get away from it all. This charming rural town is located in the Housatonic River Valley and was founded in 1724. Notable historic sites in town include Ashley House, the residence of Elizabeth Freeman, who successfully sued its owner, Colonel John Ashley, for her freedom in 1781. If you’re in the mood for a scenic stroll or nature hike, head to Bartholomew’s Cobbles Reservation just outside of town. The cobbles in question are rocky knolls that form a 1,000 ft high bedrock with sweeping views over the river valley below.

The site was designated a National Natural Landmark designation in 1971. Don’t leave Sheffield without visiting its most unique attraction, the Thom Reed UFO Monument Park. The site of the first UFO encounter in the US, the park featured on the popular TV show ‘Ancient Aliens & Unsolved Mysteries’ and has attracted thousands of curious visitors eager to explore the covered bridge where Thom Reed and his family reportedly spotted a hovering ‘white orb.’

Sugar Hill, New Hampshire

Sugar Hill Saint Matthew Chapel during fall.
Sugar Hill Saint Matthew Chapel during fall.

Gateway to the stunning White Mountains of New Hampshire, Sugar Hill is a quintessential New England town that takes its name from the colorful sugar maple trees found around town. A premier ski resort in the winter, a leaf-peeping destination in fall, and a scenic retreat in spring/summer, Sugar Hill has it all. Sugar Hill Historical Museum provides insights into the mountain town's history from 1780 to the present day. Eat like a local at Polly’s Pancake Parlor, a town landmark for over 80 years.

Housed in an 1830 building on a scenic, historic farm, this breakfast hotspot offers sweeping views over the fields to the mountains beyond. Speaking of mountains, strap on your hiking boots and walk off your pancakes at nearby Artist’s Bluff Trail, a short but stunning route that shows off the best of the rugged mountains and forest canopy.

Wickford Village, Rhode Island

Entrance of Wickford Harbor in Narragansett Bay, Rhode Island.
Entrance of Wickford Harbor in Narragansett Bay, Rhode Island.

Forget Providence; the real gem of Rhode Island is Wickford Village, a tiny town that began in 1709 as a fishing village. Today, the village is home to historic churches, colonial houses, tempting eateries, and quirky boutiques. See Main Street in style with a horse-drawn carriage tour past the historic sites or make your own tour, stopping at the Old Narragansett Church, founded in 1706, and Smith’s Castle on the western shore of Narragansett Bay.

Listed on the National Register of Historic Places, Smith’s Castle is America’s oldest surviving plantation house, built in 1678. Wickford is also a popular destination for wine lovers, with two local wineries nearby, the Langworth Farm Inn and Winery and Gooseneck Vineyards. Both offer tastings of their extensive collections.

Chester, Vermont

Aerial view of fall colors in Chester, Vermont.
Aerial view of fall colors in Chester, Vermont.

Chester is a must-see for both history lovers and outdoor enthusiasts. In the scenic Green Mountains and near the Okemo State Forest, the town is the perfect spot for hiking, biking, skiing, and hunting. It’s also home to two well-maintained historic districts — the Stone Village Historic District and Chester Village Historic District. The Stone Village is named for its collection of 19th-century stone buildings constructed by Scottish masons.

Visit the Stone House Antique Centre to browse the wares of over 90 vendors and take home some unique memorabilia. Downtown, you’ll find more examples of fascinating pre-Civil War architecture amid shops and eateries. Call in at the Historical Society Museum to grab a free guide to the town’s self-guided historical walking tour.

Off the Beaten Track in New England

New England’s small towns are the ideal destination year-round, providing breathtaking scenery and a warm welcome in every season. From Connecticut in the south to the northernmost tip of Maine, there’s so much to explore you’ll find yourself returning year after year. Discover the real New England in these often-overlooked towns suitable for every traveler, whether you’re searching for a tranquil retreat, an unforgettable adventure, or simply a break from the daily grind.

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