One Of Connecticut's Best Places To Retire Is Near Boston And Surrounded By Charming Vineyards

Connecticut retirees don't have to pick between city life and countryside relaxation. Wallingford, named among the state's top retirement communities by WorldAtlas, offers a blend of New England tradition and proximity to Boston. Plus, it has a deeply rooted history, with beginnings in the 1600s.

Local events hosted by Wallingford's Parks & Recreation Department provide retirees with many opportunities to remain active and socially engaged through art classes, fitness programs, and community events. Residents in Wallingford also have plenty of ways to unwind. Whether it's a walk along the Quinnipiac River Linear Trail, an afternoon of wine tasting at a nearby vineyard, or a night out at the Toyota Oakdale Theater, there's always something to enjoy. It's the kind of lifestyle that makes it easy to understand why so many choose to spend their golden years here, despite how much you'd need to have saved to live comfortably in Connecticut. 

Wallingford's enviable spot in Connecticut puts retirees at the crossroads of New England and the greater Northeast. The town is located 14 miles from New Haven and 27 miles from Hartford. It is also just 92 miles from New York City and 125 miles from Boston. Wallingford's proximity to the I-91 corridor allows residents easy highway accessibility for commuting into neighboring cities for daily errands. At the same time, the town is served by an Amtrak station that also connects to regional commuter rail lines, allowing retirees to craft their ideal retirement lifestyle in terms of convenience, travel, routine, socializing, or following hobbies.

This comprehensive network of transportation also places the highest-rated hospitals in easy driving or train ride distances. Yale New Haven Hospital in New Haven and Hartford Hospital in Hartford — both of which are top-rated in 2025 by U.S. News & World Report — are within driving or train distance of Wallingford, providing a sense of security for those placing priority on medical attention. Both of these hospitals also feature complete senior wellness and care programs.

There is a price for Wallingford's charm, but with careful planning, its New England appeal is still accessible for retirees. Based on a March 2025 report by the Economic Research Institute, the town's cost of living was approximately 12% higher than the national average, primarily due to housing, food, and healthcare. But renter households get somewhat of a break -– according to Apartments.com, as of May 2025, the average rent for Wallingford was $1,563 a month, 4% below the national average of $1,625. For retirees thinking of specialized senior living, facility prices might be a deterrent. Assisted living averages $11,396 per month, more than twice the state average and well above what you'd pay nationally, according to SeniorLiving.org.

Connecticut is not among the states that fully exempts Social Security income, although it does have exemptions based on income for retirees. Other types of retirement income, like pensions and withdrawals from an IRA, are taxed, but new provisions are reducing the taxability of IRA income for many. In 2024, Connecticut started implementing a state income tax exemption for traditional IRA withdrawals. Seniors with adjusted gross incomes up to $75,000 for individuals, or $100,000 for married couples, are being granted 75% of these distributions as of 2025, with full exemption by 2026. According to the State of Connecticut's Office of Policy and Management, state law provides property tax credits of up to $1,250 per year for qualifying homeowners aged 65 and older who meet specific income requirements.