An idyllic day on the lake in the Berkshire Mountains near Pittsfield, Massachusetts.

9 Best Small Towns In New England For Retirees

Small-town living has a great appeal, driven by tranquility, a slower pace of life, and tight-knit communities. Comprising ConnecticutRhode IslandMassachusettsVermontNew Hampshire, and MaineNew England is home to some of the best small towns in the United States. Each city is filled with natural beauty and unique amenities and provides a relaxed, community-oriented lifestyle. From the community meet-ups at the Barrington Stage Company Theater in Pittsfield, Massachusetts, to the peaceful Ralph Myhre Golf Course near Middlebury, Vermont, or the relaxing boat trips with a picnic on Lake Winnipesaukee near Wolfeboro, New Hampshire, these towns hold the key to a fulfilling and peaceful retirement and grant a beautiful setting to accompany seniors during their sunset years.

Lenox, Massachusetts

The Mount. Edith Wharton's home from 1902 - 1911
The Mount. Edith Wharton's home from 1902 - 1911. Image credit Adam Gladstone via Shutterstock.

The town of Lenox is a reprieve from urban hustle and bustle. With around 5,000 residents always up for a quick chat or outing, you will find a close community ready to share their easy-going culture. For art lovers, feel free to spend relaxing evenings in the Tanglewood Theatre and Shakespeare & Company, two excellent theatres that regularly host shows. Those with a knack for reading can sit at the Lenox Library. The place has been peaceful since 1815 and provides plenty of books, from old ones to new magazines, for an endless reading session. Strolling down the silent streets of Lenox, the New England architecture and historic structures create a timeless environment. With over 37% of Lenox's population in their senior years, this town allows you to meet many like-minded individuals and join a friendly neighborhood.

Auburn, Maine

Great Falls in the Maine cities of Lewiston and Auburn on a fall day.
Great Falls in the Maine cities of Lewiston and Auburn on a fall day.

If you are looking for a friendly place to keep yourself entertained throughout retirement, Auburn might be the place. Watching a play at the Community Little Theatre is a great way to socialize and give a new spin to the evening if you ever feel bored. The Norway Savings Bank Hockey Arena is another place always filled with good energy where you can cheer for your favorite team or enjoy the events. To keep fit and healthy throughout retirement, Auburn has some appealing outdoor locations, such as the Auburn Riverwalk, which features scenic surroundings and serene waves to accompany you during your walks. With the nearby Auburn-Lewiston Municipal Airport, the vicinity of its sister town, and one of the lowest crime rates in the region, Auburn is a safe bet for anyone looking to settle down.

Middlebury, Vermont

Middlebury Falls, in Middlebury, Vermont
Middlebury Falls, in Middlebury, Vermont.

Middlebury, Vermont, provides many attractions and amenities in the heart of the Green Mountains. The remarkable landscape, with the Adirondack Mountains to the west and the Green Mountains to the east, grants a breathtaking backdrop for outdoor enthusiasts. The vast Middlebury Trail Network includes the Trail Around Middlebury and the Robert Frost Interpretive Trail, both easy to tackle and beautiful. Golfers will appreciate the Ralph Myhre Golf Course, known for its stunning green hills that surround it. The Porter Medical Center is a renowned healthcare institution in the region and is an excellent option to rely upon for its many services. 

Pittsfield, Massachusetts

An idyllic day on the lake in the Berkshire Mountains
An idyllic day on the lake in the Berkshire Mountains.

Pittsfield possesses a unique urban charm. With its red-bricked buildings lining the streets and encompassing outdoor scenery, Pittsfield is a magnificent retreat and the county seat of Berkshire County. The cost of living in Pittsfield is 11% below the national average, and the average home price is $264,000, 30% below the national median, making this town a perfect option to retire in. Senior history buffs can explore the Berkshire Museum and its zoology exhibits and the ones on ancient civilizations and engineering. Community meet-ups and regular events occur weekly in the Barrington Stage Company Theater, where musicals, drama, and comedy spectacles shake up the nights in Pittsfield. Thanks to its proficient local bus system, traveling around town is easy and safe. 

Wolfeboro, New Hampshire

Aerial view of Wolfeboro historic town center at Lake Winnipesaukee
Aerial view of Wolfeboro's historic town center. 

Wolfeboro enjoys a unique setting between the small Lake Wentworth and the much larger Lake Winnipesaukee and is immersed in a sea of trees. Wolfeboro's status as a lakeside village of choice means that amenities, from dining places to healthcare facilities like the downtown Huggins Hospital complex, are as close as needed. The town has at least two designated retirement care options in the Wolfeboro Bay Center and the Taylor Sugar Hill community, providing high-quality opportunities for spending your sunset years. To relax and unwind, a short trip to the lake is a standard option, whether by private boat or commercial ferry option; a picnic on the lake is a great way to invite some friends and have some fun in the warm seasons.

Waterville, Maine

Waterville downtown landscape with path leading to lush park
Waterville downtown landscape. Image credit Feng Cheng via Shutterstock.

While it may have fewer senior citizens, the town of Waterville is ideal for people who love to indulge in the arts. The booming arts scene around here is evident everywhere you go. A visit to the stunning Colby College Museum of Art is enough to keep most people busy for days while admiring the over 7000 art pieces, including paintings, sculptures, prints, and more. Around 15,900 people also choose to experience art in a different form at the Waterville Opera House, where seniors can meet their peers while enjoying one of the performances. Taking a break from the town streets, one can also opt for quiet walks along the Quarry Road Trails, which provide scenic views of the Messalonskee Stream. Whether it's arts or nature, Waterville is a fantastic place to experience an enjoyable retirement time. 

Exeter, New Hampshire

Historic town center of Exeter, New Hampshire
The historic town center of Exeter, New Hampshire. Image credit Wangkun Jia via Shutterstock.

Exeter attracts new citizens on the older side thanks to its wide range of history and convenience. The town mixes leisure amenities, like the Exeter Country Club and its well-maintained gold course, with natural attractions, such as the pleasant views of the Squamscott River. Retirement homes like Langdon Place and the three-neighborhood RiverWoods Exeter give the discerning retiree ample choices to spend quality time with peers. Exeter Historical Society and the American Independence Museum attract culture mavens looking to relive the past through a clear new lens. Moreover, Exeter's township government maintains a lively culture and events schedule, which serves citizens and guests of any age with a social environment to keep the community close.  

Montpelier, Vermont

Montpelier, Vermont, USA town skyline.
Montpelier, Vermont, USA town skyline.

Despite being Vermont's capital city, Montpelier is still a small town with about 8,000 people. It provides a tranquil retirement destination surrounded by lush parks, forests, and the meandering Winooski River. The Central Vermont Medical Center and The University of Vermont Health Network give access to exceptional healthcare and quality services. Thanks to the Montpelier Senior Activity Center, Montpelier boasts various events that enrich the retirement experience in the area. The Savoy Arts Cinema and its recognition as one of the top 100 small arts towns in the U.S. also adds to Montpelier's appeal and provides a comfortable meeting spot for all citizens looking to experience some films together. If one wants to stretch the legs, natural attractions such as Hubbard Park and North Branch Nature Center provide many maintained walking trails to explore. Golfers might even be spoilt for choice since there are eight golf courses.

Stonington, Maine

Picturesque New England fishing village waterfront and harbor. Location: Stonington, Maine
Picturesque New England fishing village of Stonington. 

Stonington is the more secluded choice on this list, providing a picture-perfect fishing town away from big urban environments. You can sit back and enjoy the fresh air throughout your retirement. With less than 1,000 citizens, Stonington's community is very tight-knit. Stonington is jam-packed with an endless array of attractions. For example, feel free to spend your evening at the Stonington Opera House to watch a beautiful play or concert with the company of friendly neighbors. The nearby Barred Island is covered with forest and grants many trails to stretch your legs and stay fit. In between the pastel-colored houses lining the streets, you will find the famous Stonington Ice Cream Company offering 16 ice cream flavors to treat yourself after or before burning some calories. Stonington has a median age of 56, making it a good spot for retirees looking to find some like-minded peers. 

Offering everything from lavish entertainment to essential amenities, these towns in New England are some of the best retirement hubs in the region. Retirees can enjoy the benefits at a fraction of the cost, as most small towns boast affordable housing rates. Whether seeking a quiet walk along the Quarry Road Trails in Waterville, Maine, wanting to spend relaxing evenings in the Tanglewood Theatre in Lenox, Massachusetts, or just craving an ice cream from the famous Stonington Ice Cream Company in Stonington, Maine, it is clear the New England has everything it takes to spend a happy retirement. Putting it all together, it is evident why New England and its appealing states are an excellent choice for settling down. 

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