Connecticut might not be the top choice on your list of places to retire. Perhaps options like Florida or North Carolina caught your eye first. Even so, there are some amazing places to retire in Connecticut. The state does have some advantages too and, yes, some disadvantages.
Maybe some of you are already aware that retiring to Connecticut has its drawbacks, chiefly the taxes. Yes, the taxes in Connecticut are high. And unless you are former military, they tax your retirement income. However, Connecticut’s sales tax is only 6.35%, and there is no local tax. Plus, they do not have a tax on groceries.
The reality is Connecticut is expensive. Even so, there are many positive things about Connecticut that still make it an appealing place to retire. Active retirees will enjoy how walkable many of the cities and towns are, plus they will love the tons of outdoor activities this state has to offer.
And, many retirees will love how accessible New York, Long Island, and Boston are from many of the border cities—allowing you to take advantage of urban life without having to deal with the day-to-day hustle and bustle. If that isn’t enough, the long beaches and oceanfront are another benefit of retiring to Connecticut.
Connecticut also has a rich and vibrant history that is celebrated in numerous museums and historical sites. The abundance of live entertainment venues throughout the state will not let you down either. Some of the must-see spots of Connecticut are:
- Wadsworth Atheneum Museum of Art
- Yale University Art Gallery
- Mark Twain House and Museum and Harriet Beecher Stowe Center
- Opera Theater of Connecticut
- Goodspeed Opera House
- Infinity Hall Hartford
- Toyota Oakdale Theatre
Connecticut’s weather varies depending on where you live within the state. The northern parts tend to get colder than cities south and east, and the summers are best described as humid-continental, common to states that have all four seasons. And the fall colors of Connecticut are unmatched and attract tourists from all over to take in the season’s beauty.
Transportation in Connecticut is focused on making residents’ lives easier. There are several bus lines, both local and express, and passenger rails, such as the one in New Haven that connects to Grand Central in NYC. Plus, the cities throughout Connecticut are often very pedestrian-friendly, making it easy to get around without a car.
The medical care facilities are nothing to scoff at either since the list includes notable hospitals like:
- Yale New Haven Hospital
- Hartford Hospital
- St. Francis Hospital and Medical Center
We’ve researched various towns and cities and come up with our top five best cities to retire in Connecticut. We’ve been sure to include urban areas, smaller cities, and places with an abundance of activities, so you will never get bored.
Places to Retire
- New Haven
- New Milford
- Percent of Senior Population: 13.6%
- Overall Population: 130,250
Those looking to downsize to a vibrant urban area will love all that New Haven has to offer. This city has every urban convenience any retiree could imagine. It is the third-largest city in Connecticut and is home to numerous restaurants of every cuisine, plus the best pizza around.
Retirees looking for a lively city full of culture and art will find New Haven much to their liking, with options like:
- Yale Repertory Theater
- Long Warf Theater
- Shubert Theater
- Yale Center for British Art
- Yale Peabody Museum of Natural History
- Knights of Columbus Museum
New Haven is an excellent city for those looking to ditch their car and get around on foot or use public transportation. There are tons of stores, restaurants, and event venues all within walking distance from one of the many lofts or condos. Plus, if you are seeking a place with a fun nightlife, you can thank the University for the abundance of options such as bars, restaurants, and dancing.
When you are ready to get away New Haven it is as easy as getting on one of the many trains available:
- Amtrak which goes all the way to Boston and Vermont
- New Haven line that goes to NYC
- Connecting Bristol line for when you need to get to the airport
And New Haven is home to the Yale New Haven Hospital, which is the top hospital in Connecticut, according to the US News. Plus, there are numerous other medical facilities like:
- New Haven Medical Center
- Cornell Scott Hill Health Center – multiple locations
- Yale Medical Center
If you are looking to live near New Haven but prefer suburb living to city living, several nearby neighborhoods will more than meet your needs.
- Percent of Senior Population: 13.6%
- Overall Population: 84,694
Danbury, a smaller city, located in western Connecticut near the New York border, is home to one of the top municipal golf courses in the country. Retiree residents will enjoy the discounted rates that are less than half the price for non-residents. Plus, Danbury is near enough to Bloomfield so that golfers can change up their game at another premium course.
And you don’t have to be a golfer to love living in Danbury. Those looking to live on the lake will enjoy this city as it sits on Candlewood Lake, the largest lake in Connecticut. This lake provides the residents of Danbury with endless entertainment and activity options, including fishing, boating, and water sports, like canoeing and kayaking.
Because the lake is a major attraction to both residents and non-residents, the area is full of delicious restaurants, fun shops, and numerous parks around on the lake.
Though there is much to love about Danbury, when you are ready to hit the city, New York City is just over an hour away, where you can enjoy the bright lights, theater, and more.
Another aspect of Danbury retirees will love is that the temperatures are mild, only dropping to the 20s in the winter and 70s in the peak of summer. Plus, Danbury has a low crime rate of almost 50% of the national average.
Though the one drawback to Danbury is that it hosts only one major hospital, but it is home to several medical centers, including a cardiac specialty center, neurosurgical center, and neck and back specialty clinic.
- Percent of Senior Population: 15.3%
- Overall Population: 26,805
New Milford sits on the north end of Candlewood Lake and is ideal for retirees looking for quieter country living. And Candlewood Lake isn’t the only waterfront found in New Milford, as the Housatonic River also runs right through town. The Housatonic River starts in Massachusetts and is perfect for fishing, kayaking, canoeing, and rafting.
Nestled in the hills and on two waterways, New Milford draws its share of summer tourists, but the rest of the year, residents enjoy the peacefulness of the town. New Milford is the perfect location for those who enjoy the outdoors but also want easy access to the big cities, including New Haven, NYC, and Bridgeport, the largest city in Connecticut.
But you don’t need to leave New Milford to find fun things to do; New Milford is home to:
- Lovers Leap State Park, which is great for hiking and bird watching
- Bad Dream Brewing
- New Milford Historical Society and Museum
- Candlewood Valley Country Club – A premium golf course
- Harrybrooke Park
- TheatreWorks New Milford
New Milford also has its own full-service hospital. The New Milford Hospital which offers a variety of care service such as:
- Orthopedic and spine care
- Digestive diseases
- Emergency and urgent care
- Cancer Center
- Heart and vascular Center
- Primary Care
And if all of that isn’t appealing enough for you, maybe their lower crime rate will convince you that New Milford is a perfect town to retire.
- Percent of Senior Population: 24.2%
- Overall Population: 18,559
Stonington often described as a charming seaside village. Formerly a fishing community, Stonington’s economy is now driven mainly by tourism. However, the history of this fishing village is not lost. The town’s history influences all aspects of the city from the architecture to the local restaurants.
And though your first thought Stonington is likely not to be wine, there are two wineries in town. Visitors and residents shouldn’t pass up the Saltwater Farm Vineyard, where guests can take in the picturesque grounds and 15 acres of grapes. Saltwater Farm Vineyard isn’t just a tasting room either; this vineyard also hosts outdoor seating, live music, and food trucks.
If wine isn’t your thing, beer enthusiasts will enjoy the many breweries in and around the Stonington area. However, many enjoy stopping in at Beer’d Brewing Company just outside of the downtown area, for a craft pint, where they can take part in:
- Beer and cheese pairing events
- Cribbage night
- Various popup eateries
Plus, Stonington has a couple of museums, a weekly farmers market, and art studios, including the very unique The Velvet Underground Studio. The Velvet Underground Studio is not just a place to enjoy art, but also live music and drinks.
Though not in Stonington, the Foxwoods casino is just a short drive north, where you can try your luck at the tables or see one of the many live shows. And just a short drive north, residents can head to Rhode Island for a change of scenery.
Unfortunately, there are no full-service hospitals within the city limits of Stonington, but the Westerly Hospital is just a 13-minute drive from town. And for those needing greater specialty care, the Yale hospital is only an hour’s drive.
- Percent of Senior Population: 24.0%
- Overall Population: 18,030
Madison, located on Connecticut’s Long Island Sound, is one of twenty-four shoreline towns and is the perfect retirement spot for those who love the outdoors. The Hammonasset Beach State Park with 936 acres calls Madison home. The state park has both beachfront and seaside hiking any outdoor enthusiast would love. Plus, Madison also has:
- Meigs Point Nature Center
- Bauer Park
- Shoreline Greenway Trail
The small downtown area is full of fun entertainment venues, restaurants, galleries, and boutiques catering to residents and tourists alike. Because Madison is on the smaller side, it is easy to get around on foot. But for the times you are looking for the luxuries only found in the big city, Madison has an Amtrak station downtown giving residents access to NYC through the New Haven station.
Some of the other local attractions Madison has to offer, include:
- RJ Julia Booksellers – One of the largest independent bookstores in the country
- Madison Art Cinema
- The Sculpture Mile at Madison
And with New Haven just a short 20-minute drive from Madison, residents have not only the convenience of city life but also have access to numerous top-notch medical facilities.
And retirees will love the Madison Senior Center that offers a variety of programs and events such as:
- Exercise classes
- Discussion groups
- Bus tours
- Day trips
- Schiller Shoreline Institute for Lifelong Learning