Senior Resources » Best Small Towns in Connecticut

Best Small Towns in Connecticut

While it may be the third smallest state, Connecticut brims with history and charm. It’s home to Yale University, Kent Falls State Park, and the Mystic Seaport Museum. Mark Twain wrote two of his most famous works “The Adventures of Tom Sawyer” and “Huckleberry Finn” while living in Connecticut.


There are many reasons why older adults might choose to retire in Connecticut. First, the state is experiencing its lowest crime rate in decades. It also has the fifth-highest life expectancy in the United States and gives seniors access to a tuition-free education! On top of these perks, this charming New England state also boasts many attractive options for retirement living. Read on to learn more about the best places in Connecticut for retirement!



Located approximately fifteen miles from Hartford, this college town is home to Wesleyan University. The Davidson Art Center, open to visitors from September to May, proudly displays themed exhibitions featuring works by Albrecht Dürer, Rembrandt, and more. Wadsworth Falls State Park is endowed with all the waterfalls, forests, and streams that would appeal to any nature lover.



Dubbed the “Bedding Plant Capital of Connecticut”, this small town of approximately 29,000 is loaded with New England Charm. The farming community flaunts many gardens, parks, and orchids. Cheshire Hollow Farm sells pumpkins and Christmas trees during the holiday season and offers prescheduled tours year-round. Meanwhile, the annual Strawberry Festival and Craft Fair features vendors, live music, and plenty of strawberry desserts!


From boat excursions across the Connecticut River to walking tours of the historic homes on Main Street, Essex boasts an array of recreational opportunities. This is a prime location for trying out some of Connecticut’s most unique eateries. Scotch Plains Tavern offers authentic tavern-style dining with a slice of entertainment. Meanwhile, Truffle Shots serves decadent chocolate in shot glasses.

Historic lighthouse in New Haven, CT.


This picturesque town showcases rolling green hills and 18th century architecture reminiscent of Colonial times. Tapping Reeve House and Litchfield Law School, the very first law school in America, resides in Litchfield. Tour the various exhibits to learn firsthand what life was like for a 19th century law student. In the winter, nearby Mohawk Mountain boasts over 112 acres and 26 skiing trails.


Founded in 1670, Simsbury is rich in history, culture and the heritage of New England. The vibrant shopping district exhibits restaurants, antique stores, and quaint boutiques. Simsbury houses the state-of-the-art International Skating Center of Connecticut, where Olympic gold medalist Oksana Baiul once trained. The scenic and historic Old Drake Hill Flower Bridge, with 72 flower boxes and 32 hanging baskets, stretches over the Farmington River.


South Windsor

Ranked number twelve on Money’s “Best Places to Live” list in 2020, South Windsor is a great choice for any current or would-be retiree. Its top-rated school districts, low crime rate, and beautiful housing market enhance the quality of life. Around autumn, Foster Family Farm offers fun activities for the whole family, from corn mazes to hay rides. Flanked by specialty shops, upscale restaurants, and exclusive boutiques, The Promenade Shops at Evergreen Walks offers fine shopping in one convenient location.


With just under 15,000 residents, this small community is home to several tech companies. While Tolland may headquarter CNC Software’s main office, the town has not lost its historic charm. The well-preserved historic district houses over 50 buildings and residences from the 18th and 19th centuries. are what draw people’s attention to the town of Tolland. In fact, the Tolland Historical Society heads three local museums, including the Daniel Benton Homestead.


Sometimes referred to as the “Black Pearl of Fairfield County”, this idyllic farming community is full of rustic charm. Helen Keller, the famous author and disability rights advocate, spent her twilight years in Easton. Locals and tourists alike flock to Maple Row Farm around the holidays to pick up their Christmas tree and enjoy a cup of homemade cocoa.

New Hartford

New Hartford is known as the “Town for All Seasons”, and it certainly lives up to its promise! This small, close-knit community has recreational opportunities year-round. Ski Sundown, a popular ski resort, has trails for skiers and snowboarders of all skill levels. Award-winning Connecticut Valley Winery offers wine tastings and tours of its pristine vineyards.

Beacon Falls

Beacon Falls is nestled along the banks of the Naugatuck River. As such, it’s chock-full of fishing, kayaking, and canoeing opportunities! Lantern Ridge and Toby’s Pond are popular venues for outdoor recreational activities. The popular Beacon Hose Firemen’s Carnival, an annual festival featuring food and music, draws over 10,000 visitors every October.


55 Plus Communities in Connecticut

Welcome to Sleepy Hollow Hills, an active adult community that’s as enchanting as it sounds. Nestled between wooded hills and the shore village of Niantic, they offer four different home styles ranging in size between 1,600 and 2,200 square feet. Each home, regardless of the model, comes with a master bedroom suite and first floor laundry room. The town of Niantic has culture, art, and music in spades. From performances at the Ivoryton Playhouse to walks at McCook Point Park, there’s no shortage of recreational opportunities.

Originally published September 28, 2022

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