A Charming Connecticut Town Full Of Historic Architecture Is One Of The Best Places To Retire

WorldAtlas named Canterbury as one of Connecticut's best places to retire, praising the town for its delightful downtown architecture from yesteryear. This includes Prudence Crandall Museum, located in the building where the first school for African American girls existed in the area. Opened in 1833 amid controversy, the structure now serves as a National Historic Landmark for its cultural significance, and as a State Archaeological Preserve. Another site of interest in Canterbury is the Haul of Fame Trucking Museum, which is filled with vintage vehicles that could trigger fond memories. Nearly one in five Connecticut residents are aged 65 and up, making the state a retirement haven for nearly one million people. More specifically, in Canterbury, nearly 27% of residents are 65 and older.

Canterbury also contains multiple residential communities specifically for older adults. Costs to live in a senior housing unit in Canterbury average $5,628 in 2025 according to statistics provided by A Place for Mom, which totals $67,536 annually. Meanwhile, statistics from CareScout and Genworth show that the average national cost for assisted living was $5,900 ($70,800 annually) in 2024. If you'd prefer to buy a house in retirement, rather than live in a senior community, WorldAtlas also names Canterbury in its 2024 list of the most affordable retirement towns in Connecticut — thanks to the town's median home cost of just $384,500 — compared to the national average of $420,000.

Although weighing costs of living can serve as a crucial factor in choosing a place to retire, ambiance also matters. Reasons why older adults might choose Canterbury include the town's peaceful atmosphere. With approximately 5,000 residents, it's no wonder that Canterbury is located in what Connecticut refers to as its "Quiet Corner." However, quiet does not mean dull. A group called Canterbury Senior Citizens holds plenty of social events for people aged 50 and up, and the Canterbury Historical Society offers free public events to help preserve the town's heritage. 

Meanwhile, older adults can enjoy the walking trails in Robert Manship Park and Kinne Preserve as well as Connecticut's beautiful scenery. Residents can observe this across all four seasons — something that Florida snowbirds don't get to enjoy. The town also celebrates the Fourth of July in style with a parade with the parks serving as enticing post-parade picnic spots. Plus, friends and family can visit via National Scenic Byway SR 169, and the Bradley International Airport is just 54 miles away, making it easy to travel in and out of the quaint town of Canterbury.

When looking for city activities to enjoy, Canterbury is just 35 miles from Providence, Rhode Island. There, older adults can enjoy a range of dining and shopping venues and even go on narrated river boat rides. Providence is also chock full of museums to tour and enjoy: the elegant John Brown House Museum, the Museum of Natural History and Planetarium, and the Governor Henry Lippett House Museum.

To enjoy your optimal retirement, and all that Canterbury has to offer, it's important to continue monitoring the best investment opportunities for retirees in order to make the most of your saved money. Plus, there are plenty of ways to keep earning money post-retirement that don't involve the workforce. With that said, you can always supplement your income by working. According to the CNBC Your Money Retirement survey in August 2024, 17% of retirees are working by choice — meaning, not because they financially need to keep working. Another 11% keep working because they could use the extra income. 

Although working retirees may remain in the fields that brought them income pre-retirement, others choose different encore careers in which they select employment opportunities that bring them fulfillment. When considering whether to work after retirement, it's important to consider what kinds of income won't have an effect on Social Security benefits. If you began collecting Social Security benefits before reaching full retirement (which is now 67, but used to be earlier), the maximum allowable amount you can earn in 2025 without penalties before reaching full retirement age is $23,400.