10 Tucked-Away Treasures to Retire in Connecticut

Connecticut regularly tops “best places to retire” lists. It’s known for its natural beauty, friendly people, safe communities, and healthy residents. A long coastline, acres of wooded forests, and picturesque mountain ranges offer a little something for every type of nature lover.

More than 100 parks throughout the state help seniors pursue wellness as they enjoy the outdoors. There are plenty of hiking, biking, fishing, and boating opportunities. Arts and cultural offerings abound, and a highly-ranked healthcare system is another benefit to aging residents.

If you’re looking to retire in Connecticut, the ten towns we highlight here offer a slower pace, lower stress, and higher quality of life.

1. Westport

About 50 miles from New York City, Westport, CT, offers small-town coastal charm with big-city amenities only a short ride away. Westport’s population is around 28,000 people.

Westport is located in Fairfield County and sits along the Long Island Sound. When retirees aren’t enjoying sand and surf along one of Westport’s many beaches, they have plenty of other activities from which to choose. Westport is long known for its shopping, dining, and sightseeing options, as well as art galleries, performing arts venues, and numerous parks.

2. Litchfield

If you’re looking to experience a classic New England town for your golden years, look no further than Litchfield, CT. An important town during the Revolutionary War, Litchfield served as the location for George Washington’s meeting with Colonel Tallmadge, who led Washington’s “secret service.”

Seniors will enjoy a quaint, small-town shopping and dining experience in Litchfield. Bantam Lake and the White Memorial Conservation Center offer opportunities for participating in water sports and nature exploration.

Only 1,200 people call Litchfield, CT, home.

3. Simsbury

Promising “heritage, charm, adventure” on a site promoting tourism, Simsbury, CT, lives up to its slogan and then some. The National Trust for Historic Preservation lists Simsbury as one of its “Dozen Distinctive Destinations.” It’s also a federally designated “Preserve America” Community.

Providing a high standard of healthcare, Simsbury is home to renowned medical facilities. Both Hartford Hospital and the University of Connecticut Health Center are located in Simsbury.

Retirees enjoy Simsbury’s historic downtown area. Outdoor activities include biking, hiking, and kayaking. Leaf peepers enjoy stunning displays of colorful foliage each fall. About 24,000 people reside in Simsbury.

4. Glastonbury

Located along nine miles of the Connecticut River, Glastonbury is yet another small town steeped in American history.

If you’re interested in Colonial architecture, you should consider retiring to Glastonbury. With more than 150 houses built before 1800, Glastonbury has the second-most Colonial houses of any town in the country. Four houses in Glastonbury date to the 1600s.

Glastonbury’s oldest house, the John Hollister House, was built around 1675. It’s one of the oldest in the nation and one of the oldest five houses in Connecticut. You can also visit several historic sites and museums, including the Welles-Shipman-Ward House and the Connecticut Audubon Society Center.

Less than a two-hour drive to New York City and Boston, Glastonbury’s population numbers about 35,000 people.

5. Newtown

Famous for the friendliness of its people, Newtown, CT, offers seniors the best of a cozy, suburban feel only about 60 miles from New York City. There’s no shortage of fun events for active seniors in Newtown.

Science centers, parks, and botanical gardens all offer opportunities to engage with nature. Sports enthusiasts will have fun playing golf and tennis, and the artistically inclined will enjoy art galleries, live theater, and craft fairs. Foodies will expand their palettes as they dine at food truck festivals and tour wineries, breweries, and vineyards.

Autumn is an especially festive time when Newtown hosts fall festivals, apple picking, corn mazes, and pumpkin patch tours. Combined with the colorful display of autumnal canopies, these activities are ideal for seniors looking for a charming place to call home.

6. Cornwall

What makes Cornwall, CT, a retirement destination? Aside from its iconic covered bridges, stunning natural beauty, and opportunities for outdoor activities, the town’s traditions appeal to seniors looking for fun ways to become active members of the community.

Cornwall sounds like a town you’d see in a Hallmark movie: full of charm galore and a tight-knit group of neighbors ready to celebrate the latest holiday with old customs. The townspeople sponsor an annual Memorial Day parade, a race among firefighters in full gear to fundraise for charity, and the annual Cornwall Woman’s Society rummage sale each July.

Residents keep tabs on it all through the monthly Cornwall Chronicle, the town’s volunteer-produced, non-profit, and non-partisan newspaper.

Fewer than 1,500 people live in Cornwall, CT.

7. Putnam

If you’d like to live in a quaint community on the river’s edge, then Putnam may be perfect for you. Located along the Quinebaug River, Putnam is a nature lover’s paradise. Retirees here enjoy hiking, biking, and swimming.

Recent downtown renovations offer residents and visitors unique shopping and dining experiences, as well as live entertainment.

Numbering about 9,000 residents, Putnam is like Goldilocks. It’s not too big or too small; it’s just right!

8. Milford

Like so many of its peer locations in Connecticut, Milford ranks high with retirees for its inherent natural beauty. Located on the coast, Milford provides numerous outdoor activities for its residents and visitors. Water sports lovers can always enjoy boating, swimming, or fishing in the waters of Milford.

With a low crime rate and a reputation for being friendly, Milford is a safe and secure community, which is important to seniors.

The population of Milford, CT, is about 50,000 residents.

9. Old Saybrook

Old Saybrook, CT, dates from the early 1600s. It’s a beautiful town of about 10,000 people. Situated on 17 miles of coastline, Old Saybrook is full of historic charm.

Once home to actor Katherine Hepburn, Old Saybrook named its arts center and theater “The Kate” in honor of her. Seniors enjoy live entertainment there as well as historical events sponsored by the historical society.

The Great Cedar Conservation Area, the Clark Community Park, Fort Saybrook, and the McKinney Wildlife Refuge all offer opportunities for nature lovers to sightsee and bird-watch. 

10. Middletown

If you’d like to live in a college town during your golden years, Middletown, CT, may be right for you. Home to Wesleyan University, Middletown has many shopping, dining, and cultural offerings.

The highly-ranked Middlesex Hospital attracts seniors to Middletown, and the small city’s centrality in the state means that amenities in Hartford or New Haven are just a short ride away.

Summary of 10 Tucked-Away Treasures to Retire in Connecticut

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