Historic buildings and shops in Perkins Cove in Ogunquit, Maine. Image credit Wangkun Jia via Shutterstock

9 Most Memorable Small Towns in New England

When it comes to exploring small-town life, New England can offer quite the experience to its visitors. Located in the northeastern part of the United States, New England is home to six states, New Hampshire, Rhode Island, Maine, Connecticut, Vermont, and Massachusetts. Each of these states has charming small towns that take you back in time. With streets echoing the colonial history of the country, and beautiful bays, forests, and mountains covering the landscape, these nine most memorable small towns in New England are a must-visit!

Woodstock, Vermont

Ottauquechee River flowing through Woodstock, Vermont.
Ottauquechee River flowing through Woodstock, Vermont.

Nestled in the heart of Vermont, Woodstock is the quintessential American small town with several charming elements, including preserved Victorian mansions that date back to the 19th century. Besides the mansions, visitors can also look forward to exploring scenic cheese and maple farms as well as beautiful covered bridges. With the Green Mountains as its backdrop, Woodstock is an extremely photogenic town. One of its prime beauties is the Ottauquechee River, which has helped shape various natural wonders of the state, such as the famous Quechee Gorge.

Another must-visit destination in Woodstock is the Marsh-Billings-Rockefeller National Historical Park, the state’s only national park, which boasts a variety of wetlands, glacial features, and tree strands. Animal species that tourists may spot at the park include the white-tailed deer, barred owls, wood ducks, painted turtles, and fishers.

North Conway, New Hampshire

Train station, North Conway, New Hampshire.
Train station, North Conway, New Hampshire. Image credit Keith J Finks via Shutterstock.com

Sitting at the corner of the Mount Washington Valley and White Mountains in the state of New Hampshire, is North Conway. Often referred to as a resort town, North Conway is popular among tourists looking for short weekend getaways. From beautiful ski resorts and breathtaking wilderness areas to fine restaurants and top-notch bed and breakfasts, North Conway offers a complete package deal for a fun and relaxing holiday!

For those who like to explore a town on wheels, driving on the 34-mile-long Kancamagus Scenic Byway is an absolute must. It is known for its gorgeous fall foliage. The byway also passes through the White Mountain National Forest, located between Lincoln and North Conway. Don’t miss seeing the Albany Covered Bridge and waterfalls like Diana’s Baths on your way!

Mystic, Connecticut

Mystic Seaport, an outdoor recreated 19th-century village and educational maritime museum in Mystic, Connecticut.
Mystic Seaport in Mystic, Connecticut. Image credit Faina Gurevich via Shutterstock.com

Mystic, a small town in Connecticut, earned quite a bit of fame from the 1988 rom-com ‘Mystic Pizza,’ starring Julia Roberts. The movie was quite an accurate portrayal of the seaport town and its idyllic spirit, which remains intact to date. Mystic Seaport is known for its huge collection of ancient watercraft. This includes Charles W. Morgan, a 19th-century whaling ship, as well as the nearby USS Nautilus. The latter was the first submarine powered by nuclear energy in the United States. Despite being a small town, Mystic has a plethora of must-see attractions.

Take a day to walk around the historic downtown, lined with quaint, charming shops. Don’t forget to get a few shots of the majestic Mystic River Bascule Bridge, and enjoy a nice meal in the Olde Mistick Village. Tourists can also take guided tours along the beautiful coastline to get a close view of ancient landmarks such as the Mystic Seaport Museum.

Ogunquit, Maine

Fishing boats docked in Perkins Cove, Ogunquit, on coast of Maine south of Portland
Fishing boats docked in Perkins Cove, Ogunquit, Maine.

Ogunquit is a serene seaside town in Maine with blooming wildflowers, making it a picturesque and memorable destination for tourists. The town is known for historic clapboard buildings and beachy cottages. Lobster fans will absolutely love Ogunquit because they can enjoy eating at popular lobster spots such as Lobster Pound, Oarweed, and Barnacle Billy’s. The best part? These eateries remain open till the fall. For outdoor enthusiasts, it would be a shame to miss a biking tour near Ogunquit.

There are several scenic routes, such as the Shore Road (a coastline route), or the Berwicks and Mt. Agamenticus. Ogunquit is also home to stunning beaches like Footbridge Beach and Wells Beach, which are excellent places to relax and enjoy a picnic with friends and family.

Westerly, Rhode Island

Image of the Martin House in Westerly, Rhode Island, USA. Editorial credit: Rachel Rose Boucher / Shutterstock.com
Martin House in Westerly, Rhode Island. Image credit Rachel Rose Boucher via Shutterstock.com

Westerly might be a small town in Rhode Island, but it is known for its thriving downtown, full of amazing restaurants, trendy bars, beautiful beaches and shopping boutiques. Its Watch Hill Beach and Misquamicut Beach are absolutely swoonworthy. Watch Hill is a small beach located behind the old Flying Horse Carousel. It is home to a bathhouse and is especially popular among families.

Misquamicut State Beach, on the other hand, features modern beach facilities, such as outdoor showers, shade gazebos, and a playground. It also has a beachfront that runs for half a mile. When in Westerly, don’t forget to visit the Vesta Bakery for mouthwatering cream puffs and the Tapped Apple Cidery and Winery for amazing white wine!

Stowe, Vermont

Aerial view of the charming town of Stowe, Vermont.
Overlooking the charming town of Stowe, Vermont.

While Vermont has several beautiful towns to visit, Stowe probably gets the maximum influx of tourists during winter. This is primarily because it has slowly become a prime ski destination attracting snowboarders and skiers to the magnificent Mount Mansfield (4,393-foot tall peak). But Stowe has something to offer to its visitors in every season; summer is a great time for outdoor adventure, while spring is all about maple sugaring.

The town hosts several exciting annual events, such as the Winter Rendezvous, Stowe Foliage Arts Festival, and Stowe Farmers Market, among others. Some popular places to eat in Stowe include Tipsy Trout, Alpine Hall, and Matterhorn.

Chilmark, Massachusetts

Menemsha Harbor, Chilmark, Martha's Vineyard, Massachusetts.
Menemsha Harbor, Chilmark, Massachusetts.

Chilmark is one of the three popular up-Island towns in Massachusetts, the other two being West Tisbury and Aquinnah. This quaint, charming town is home to various preserves and sanctuaries that offer a variety of fishing spots and walking trails. One of the recommended hikes is through the Waskosim’s Rock Reservation, which offers breathtaking views from the hilltop. Another beautiful spot for walking is the Peaked Hill Reservation. Both parks are under the management of the Martha’s Vineyard Land Bank.

Martha’s Vineyard is widely known for its sun-kissed waters and stunning coastlines. With a more rural vibe, Chilmark is home to Menemsha, a fishing village (be ready to savor delicious lobster rolls and chowder among other local dishes!).

Bar Harbor, Maine

Aerial view of Bar Harbor, Maine.
Overlooking the stunning Bar Harbor, Maine.

Known to be an entryway to the famous Acadia National Park, Bar Harbor is a small town located on Mount Desert Island. It is home to the Cadillac Mountain, the eastern seaboard’s highest point, where one can possibly witness the first sunrise of the country. The seaside hamlet is particularly busy between May and October because several tourists visit to enjoy whale watching as well as Eden Farmers’ Market. Some of New England and Maine’s best restaurants are in Bar Harbor.

These include the West Street Cafe, CIAO, and the Side Street Cafe. Within Bar Harbor, tourists can find rocky beaches, boreal forests, glacial-formed valleys, and lakes.

Manchester, Vermont

Equinox Pond and Mount Equinox at the Equinox Preservation Trust in Manchester, Vermont.
Equinox Pond and Mount Equinox at the Equinox Preservation Trust in Manchester, Vermont.

Planning a fun family outdoor adventure? Manchester in Vermont could be the perfect destination! The population of the town is less than 5,000, and it is enveloped by the Green and Taconic Mountains. These mountains are ideal for scenic nature excursions from places such as Mount Equinox (3,848 feet tall) and the Lye Brook Falls trail. When visiting in autumn, don’t miss the opportunity to pick up pumpkins at the Equinox Valley Nursery. Also, tourists are encouraged to buy handcrafted souvenirs from Manchester Woodcraft.

New England is essentially responsible for inventing the concept of scenic all-American towns. So, don’t miss a chance to visit one of these nine memorable towns in the state on your next vacation.

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