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There is something so quaint about Connecticut towns. Villages right out of a Charles Wysocki painting. One can imagine how he’d capture one of Connecticut's seaside settlements. With the ships in the harbor at full mast, the dock workers and shipbuilders busily toiling away. Perhaps a young boy catching a fish and an old sea captain, looking on as a little trail of smoke escapes his pipe. The backdrop of the town with the charisma of its Colonial architecture. Billowy clouds on the horizon, and the sun shimmering off the choppy Atlantic. Envisage the autumn with the dense trees ablaze with color and the stately homes lining the shore.

Thankfully, one doesn't have to imagine it. These towns exist and are among the perfect spots to spend one's golden years. Towns with rich natural beauty, deep history, culture, and local attractions. Additional criteria considered for the list included factors like walkability, affordability, and access to medical care — all the things one needs to consider as they age.

Mystic

Consistently ranked as one of the top retirement towns in Connecticut, this seaside village is bursting with New England charm. The downtown is walkable, and the village is on the train route, with quick access to Boston and New York. Mystic is about 10 miles southeast of New London, and it's full of landmarks like the Bascule Bridge.

Not only do the natural beauties of the harbor and seascapes abound, but the village has a rich American history. First settled in 1654, it served as a safe harbor port for ships during many storms and was a major ship-building hub and maritime destination for centuries. Today, one can visit the Mystic Seaport Museum to experience that history. There is also a top-tier aquarium. The downtown offers a proud foodie scene. From Mystic Pizza, made famous by Julia Roberts, to Nana’s fresh sourdough doughnuts to Sea Swirl’s fried whole-belly clams, be sure to bring one's hunger!

Simsbury

Located about 10 miles from Hartford, Simsbury is an inland town that lies along the Farmington River. Incorporated in 1670, Simsbury was the 21st town to incorporate in Connecticut. Talcott Mountain State Park has the best views in the area, especially from the 165-foot Heublein Tower. One's eyes will be met with rolling hills, dense forests, and picturesque farmlands. The river provides the opportunity for fly fishing and canoeing. The downtown has fine restaurants, such as Abigail’s Grille and Wine Bar, for all-American eats in a Revolutionary War-era tavern.

Natural beauty, and walking and biking paths make Simsbury a highly desirable location for retirees. Hartford Hospital (located roughly 20 minutes away by car in the city of Hartford) is one of the best hospitals in the state, according to US News and º£½ÇÉçÇø Report's Best Hospitals. Hartford Hospital specializes in cancer, cardiology, and diabetes. Having access to the best medical care is critical to keeping one healthy, active, and making the most of the retirement years. Stretching a fixed income is key, and thankfully, Simsbury’s home prices (between 2017 and 2021) sit at an average median home price of $315,800, according to the US Census Bureau.

Madison

In the center of Connecticut’s Long Island Sound shoreline, Madison is often ranked among the top towns to retire in the state. Located about 20 miles east of New Haven, the town is full of historic homes and amazing waterscapes. Hammonasset Beach is a two-mile stretch of water activities like swimming and scuba and land pleasures like summer camping, picnicking, hiking, and biking. The Meigs Point Nature Center, is another great space to experience the outdoors and see wildlife. The downtown has boutique shops, such as J.R. Julia Booksellers, where one could spend half a day leisurely browsing and reading in this charming brick bookstore or stop for a bite at Café Allegre, located in a lovely white inn with an excellent Italian menu.

New Haven, which is only a short ride away, is home to the top hospital in the state, Yale Hospital, according to US News. The downtown isn’t fully walkable, in that it's too spread out to see all of it on foot and requires transportation, but there are many sidewalks and paths in the town, which make it pedestrian-friendly. 

New Canaan

The town center of New Canaan brings everyone together, as it hosts the main shopping for the area. New Canaan isn’t as expensive as some of the nearby coastal towns, but it’s probably not for those on a tight budget. The median home price between 2017 and 2021 was $947,200, according to the US Census Bureau. New Canaan is known as a peaceful community with good schools. It’s on the train route, and that makes travel easy for those who commute and those who don’t drive. 

Located about 8 miles from Stamford and only an hour from New York City, New Canaan is close to the major metros by train but offers a bit more elbow room. Historical landmarks include The Glass House, which is an architectural trendsetter, and Waveny Park, with its 1912 castle and 300 acres of trails, fields, and ponds. New Canaan is a charming town that makes for a good retirement location for those looking to escape New York and Boston for breathing room and a slower pace.

Litchfield

Columnist C.J. Hughes, in a recent New York Times article, described Litchfield this way, "Being old-fashioned is a point of pride in pastoral Litchfield, where farms sell raw milk, residents traverse their properties on horses, and houses are older than America itself." Litchfield has been home to several notables, including actor Dustin Hoffman, actor and comedian Denis Leary, and the late Marilyn Monroe and her husband (at the time) playwright Arthur Miller.

It’s easy to see why this quintessential 18th-century New England town is so popular. It is known for its rolling hills, tranquil lakes like Bantam Lake, and its historic downtown with its cute shops and restaurants. Peaches N Cream is a delicious ice cream shop that will satisfy one's sweet tooth. Litchfield is about 30 miles from Hartford, which gives one access to the best hospitals and doctors at Hartford Hospital.

Guilford

Located 14 miles east of New Haven is the scenic town of Guilford, which has that old New England feel many are looking for. Settled by the Puritans in 1639, Guilford has a more rural, seaside feel. Known for its Guilford Green, an almost 12-acre park with a Civil War memorial at the center, this park has been frequently voted one of the best in the state. Around the park, one will see traditional buildings from the period and a white-steepled church. There’s a lovely tree-lighting event every year during the Christmas season. 

The historic downtown, with its tree-lined streets, mature homes, shops, and restaurants, is like a scene out of a movie. Bishop’s Orchards Farm Market and Winery has been in operation since 1871 and is as enchanting as a market gets. Many retirees move here from New York for a more relaxed way of life. The town has a par three golf course and other courses in nearby towns.

Chester

Chester is a unique town with eye-catching architecture, shops, art galleries, and first-rate restaurants. Brushmill by the Waterfall is a delightful restaurant by a serene waterfall. Settled in 1692, the town is near the Connecticut River, and the thick forests are a foliage paradise in the autumn. The nearby Cockaponset State Forest has over 17,000 acres to explore, with so much nature and wildlife to see on foot or by bicycle.

On Saturday nights in the spring and summer months, one can enjoy concerts in the garden at Leif Nilsson Spring Street Studio and Gallery. The Goodspeed Opera House is also a great place to enjoy music.

Woodbury

The quiet, quaint, 350-year-old town of Woodbury has everything a retiree might be dreaming of. The downtown has remarkable antique shops, colloquially referred to as the "Antique Capital of Connecticut." Mill House Antiques is one such example, with its remarkable collection of treasures. The waterfall and greenhouse on the property are a nice touch. The 1754 House Inn and Restaurant has a cozy ambiance and a nourishing menu. 

Main Street has gentle greens, tree-lined streets, a community bandstand, and homes from the 17th, 18th, and 19th centuries. There’s a true hometown feel to Woodbury, with friendly residents and a more robust full-time population of just under 10,000 compared to some of the surrounding towns. Experience wildlife at the Highwire Deer and Animal Farm and enjoy nature at Flanders Nature Center.

Retire to Connecticut

Leave the big city behind and find a slower pace in Connecticut. Each of these towns has something special to offer, from seaside villages to the rolling hills of the country. Connecticut really should be on one's list of retirement locations to consider.