9 Best Small Towns to Retire in Connecticut in 2024

Let’s start with the bad news. Connecticut is not the most tax-friendly. Its sales tax, for instance, is among the highest in the country. But here is the truth: Tax-friendliness is just one factor a retiree should consider. Connecticut scores big on quality of life, healthcare access, safety of neighborhoods, education, and retirement-age population. Besides, its stunning coastline is dotted with numerous quaint towns such as Mystic—and can be perfect for those who want to retire right on the water. If you are considering retiring in the Constitution State, discover below the nine best small towns to retire in Connecticut.

Old Saybrook

Forget about its “old” tag; this Connecticut treasure is a small town of just about 2,000 residents that looks anything but old. Considering its size, this town particularly scores big on amenities, including shops and restaurants. Plus, Old Saybrook boasts one of Connecticut's most walkable main streets. Old Saybrook should be on your radar if you are a fan of concerts, movies, and theaters because it hosts the one-of-a-kind Katharine Hepburn Cultural Arts Center. Since this town is right on the water, the winters here are not as brutal. Hammonasset Beach State Park, Connecticut’s largest shoreline park, is just 14 miles down the road. And New London, which offers a rich menu of cultural amenities, is just within smelling distance. You may love the fact that Lawrence and Memorial Hospital in New London has been recognized for the Outpatient Joint Replacement Excellence Award. With a median age of 57, a retiree here will feel part of a big, supportive family.

Glastonbury

One of the best parts of retiring in Glastonbury, other than the fact it is just about 9 miles from downtown Hartford, is the presence of the river-fronting Gay City State Park as well as the Shenipsit Trail. These spots are awesome and can make for an exciting early-morning routine. Besides, you will be close to the state capital and the fourth-largest city in the Constitution State. Therefore, expect an impressive array of amenities, including excellent hospitals and shopping venues. With a median age that grazes the 50-year mark, you will find peers in the same age bracket who can recognize the tunes of Bob Dylan, The Beatles, and Marvin Gaye. Finally, Glastonbury is known to be safe, friendly, and walkable — features that most retirees prioritize.

Mystic

While Sift Bake’s pastries and deserts draw hordes from across the region—and is a facility residents and visitors often rave about—Mystic is home to much more. The Velvet Mill, which is less than 5 minutes away in Stonington, is an awesome shopping venue that will meet nearly all your retail needs. The downtown is adorable and chockful of attractions, including the Mystic drawbridge, the oldest drawbridge of its type still in the nation. The town’s median age stands at 54 years. According to niche.com, seniors aged 55 and above comprise 51% of the town’s population. This means you will enjoy the company of folks in the same age bracket. Plus, New London is just 9 miles away via Interstate 95—while Westerly, Rhode Island, home to the award-winning Westerly Hospital, is even closer. That said, homes in Mystic fetch a median price of $697,000.

Orange

One of Orange’s retirement appeals lies in the fact it is just about 6 miles to West Haven and, hence, scores big on access to amenities. Yale New Haven Hospital, for instance, is among the 250 best hospitals in the United States. Phipps Plaza in New Haven is a nice shopping venue. It hosts unique niche stores such as Slither & Swim, which is known for its great selection of fish and plants. There is also a train ride to both New York and Boston, two cities that score high on cultural attractions. Also, Orange boasts a median age of 44—meaning you will not find yourself lonely or friendless. That said, the housing market here is increasingly becoming quite competitive. Homes in Orange, whose median price is $543,000, sell after only 35 days on the market. In the previous year, homes here were being sold after 81 days on the market. One may want to put this to the fact Orange is safe, mostly middle-class, and enticingly quiet.

Southbury

Southbury is a small but vibrant town of about 20,000 residents that any retiree will find irresistible. Some of Southbury's most exciting features are lots of fresh, local produce, excellent schools— which is crucial if you have school-going children—and safe neighborhoods. Homes here fetch a median price of about $399,000, which, considering the area, is not a bad price point. Heritage Village, which is encircled by scenic trails and natural ponds, is a well-known adult community any retiree may want to check out. New Milford, Danbury, Waterbury, and Derby—are all just 20 minutes away or less. Plus, Griffin Hospital in Derby is the Outstanding Patient Experience Award recipient and is a go-to venue for medical services in the area.

Essex

Well-maintained storybook houses dot the hilly neighborhoods of this Connecticut charmer, earning it a spot among the best towns to retire in the state. The Griswold Inn, located right on Main Street, could be the oldest continuously operating Inn in Connecticut and all of America. Known to be safe and family-friendly, Essex is small but incredibly charming. The town plays host to just about 6,700 residents. While you cannot miss to find essentials here, Essex is conveniently close to several towns where one can access even more amenities. For instance, Middletown, which hosts the reputable Middlesex Hospital, is a 20-minute drive. The same is true of New London, where the award-winning Lawrence and Memorial Hospital is located. With a median age of 54 years, you will easily find fellow seniors with whom you can curate an active social support network.

West Simsbury

West Simsbury should tickle your fancy if you do not fancy a dense, suburban feel but a laid-back, rural one. Home to just about 3,000 residents, West Simsbury hosts the Tulmeadow Farm, an old ice cream haunt that spans more than 260 acres besides offering at least 20 farm-made flavors. Expect plenty of restaurants and parks, relative peace and tranquility, wonderful bike trails, and proximity to amenities. Hartford is a short drive away; hence, one's medical and shopping needs will be easily met and fulfilled. With a median age of 54, retirees here will feel like they are in familiar territory. The most exciting part about retiring here, however, is the fact homes fetch a median price of just $190,000!

Avon

While it is not the most walkable, Avon features breathtaking views of hills and mountains and boasts plenty of outdoor activities, including hiking, kayaking, and skiing. The Farmington Canal Heritage Trail, which is over two centuries old, can be an awesome venue for early-morning strolls or biking. A retiree will need to burn his legs once in a while and fill his lungs with some fresh, crisp air. And if you want to tee off your evenings away, the 18-hole Blue Fox Run Golf Course will be at hand. Residents above 45 years make up an impressive 50% of Avon’s population. This means you can easily link up with similarly-aged friends and reminisce about the good old days. With Hartford just 9 miles down the road, a retiree here will enjoy excellent access to healthcare. Hartford Hospital, for instance, is in the top 250 hospitals in the nation.

Sherman

Candlewood Lake. That is one reason you will want to pitch your tent here. Not only is Candlewood Lake a great spot for fishing for smallmouth bass but it is also just beautiful and imbues the area with a delicious, rustic look. Expect a rural feel here and noticeably peaceful, safe, and laid-back settings. Boasting a median age of 58.2, a retiree here will be interacting with fellow empty nesters and sharing relevant experiences. While you can find essentials in town, Sherman is conveniently close to New Milford, Danbury, and Carmel. One can access New Milford Hospital, a recipient of America’s 100 Best Hospitals for Gastrointestinal Surgery Award, in a jiffy. That said, Sherman is relatively affluent. Homes here fetch a median price of $615,500.

Home to one of the most prestigious universities in the world, Connecticut is the nation's third-most educated state. Retirement here will come with mingling with well-informed folks, whether in restaurants, hiking trails, or neighborhood get-togethers. Plus, the Constitution States boasts top-notch amenities and is known for its close ties to New York. From Old Saybrook to Sherman, this Southern New England state is star-studded with quaint and charming small towns, most of which can be awesome retirement spots. Other than these two towns, the best small towns to retire in Connecticut include Glastonbury, Mystic, and Orange.