States – Connecticut


Connecticut is an attractive place to live because of its scenery and central location. It has gently rolling hills, grasslands with farmhouses, and woodlands that turn into spectacular reds and yellows in the fall. It’s also just a few hours drive or train ride to New York and Boston from most anywhere in the Constitution State.

But the high cost of living and taxes are a big drawback. Connecticut had the third highest tax rates in the U.S. in 2009. The income tax rate is as high as 6.7%, and Social Security benefits and pensions are taxable depending on income. The proximity to New York also means that many highly paid professionals live in the state, which drives up costs. In some places the median home price exceeds $1 million, and the overall cost of living in the state is three times the national average.

In Bridgeport, for example, renters age 60 or over in 2013 paid an average of $854 per month in rent, while retired homeowners paid $2,440 in monthly mortgage. The high costs led USNews to rank Bridgeport among the 10 worst places to retire in the U.S.

There are places where you can enjoy the benefits without the high cost. Here are a few worth a look.


Once the third most populous city in the state, Litchfield is now a town of around 10,000 with lots of appeal. Although it’s a small town, Litchfield and its neighboring towns have plenty to offer. It has stately, Nineteenth Century mansions lining the streets, and a picturesque Congregational Church with a white steeple in the center of town. There are also various shops, restaurants, and pubs in the town center.

Those interested in exploring the area’s history can take a self guided walking tour, which includes the Plymouth Burying Ground, with gravestones dating to 1749, several historic buildings dating to the Revolutionary War, and a house that was a stop on the Underground Railroad. There’s also the nearby American Indian Museum, which tells the story of indigenous peoples of the northeast.

Those interested in art can follow the Connecticut Art Trail, which covers 15 major museums and exhibit sites including historic sites, rustic farms, art studios and artists’ houses, as well as grand and modern art museums. Residents can also explore the wineries, orchards, and farm stands covered on the seven different routes of the Connecticut Barn Trail.

Nearby in Torrington, a 10-minute drive away, is the Warner Theater, which has a full slate of modern and classic movies and is also an Art Deco exhibit in itself, with chandeliers and murals.

The town offers many outdoor adventures as well. Without leaving town, you can climb to the top of Mount Tom, sail on Bantam Lake, the largest natural lake in the state, cross-country ski through Topsmead State Forest or hike for miles through White’s Woods, part of the 4,000-acre White Memorial Foundation. In the summer you can also take a 2.5-mile tube ride down the Farmington River, crossing three sets of rapids in the process.


With Wesleyan University in the center of town, Middletown is a college town with a nice view of the Connecticut River and very affordable housing. There are many condos in town, with a median price of $150,000. In 2015 a two-bedroom, two-bath condo was selling for $139,000, while a 1,600 square foot home was selling for $260,000.

Residents will find many activities in town. On and around the university campus are bookstores, shops and restaurants, and a museum, galleries, theater, lectures, and sports events. There are also many parks and nature trails including the Middletown Nature Gardens, Wadsworth Falls State Park and Smith Park, and the 100 acre-Guida Farm Conservation Area.

Harbor Park is a 2.6-acre recreation area on the Connecticut River, featuring a boardwalk, restaurant/nightclub, fishing, seasonal boat excursions. The Fourth of July celebration and the Head of the Connecticut Regatta event in October are held at Harbor Park. Golfers can take on the 54 holes at the Lyman Orchards Golf Club, or one of the public golf courses nearby.

The Goodspeed Opera House in town, built in 1876, is considered the birthplace of musical theater and still hosts regular performances. Visiting grandchildren can indulge their imaginations at the Kid City Museum. Those who are adventurous can learn swimming, scuba diving, or kayaking at the Brownstone Explore & Discover Park, or skiing and mountain biking at Powder Ridge Mountain Park & Resort.

Shoppers will like the 70 retailers at Clinton Crossing Outlets, 25 miles away. Middletown has good health care available through Middlesex Hospital, a major employer in Middletown and throughout Middlesex County, which is spending $31 million to build a new emergency department. Middletown is just 16 miles from Hartford, and a half-hour from the Atlantic coast.

East Lyme

If you want to live closer to the coast, and enjoy a mild climate, East Lyme might be the place. In January the high and low temperatures are 38 and 24 degrees, and in October, they’re 63 and 48. In addition, it snows on average about 50 inches inland and only 30 inches in East Lyme.

In the summer and fall, strolls along the town’s mile-long boardwalk or the beach at Rocky Neck State Park are local pastimes.  The maritime village of Niantic is within easy walking distance of town and the waterfront, and offers shopping and dining. A new development of 150 one- and two-bedroom apartments and townhouses recently opened there as well. A cancer center opened recently in Waterford, 10 minutes away, and Yale-New Haven Hospital is less than an hour’s drive.

New Milford

New Milford offers quiet country living in the hills, valleys, and green pastures of New England. There’s lakefront property on Candlewood Lake (Connecticut’s largest), and many properties along the rural back roads of the countryside. The Housatonic River runs for miles right down the middle of the town, offering kayaking and boating.

New Milford offers a variety of housing choices and sizes for retirees including many condos, and homes in three senior communities. The town has a busy senior center, and many volunteer opportunities. There’s an 18-hole public golf course at The Candlewood Valley Country Club and three more private golf courses are in neighboring communities. Hikers and bikers can explore the Appalachian Trail as well as numerous other trails and public parks, while boaters and swimmers can enjoy Candlewood Lake.

For more information about retirement in Connecticut:

State overview in facts and figures

State taxes

State services for senior residents

Profiles of major cities

Retirement communities

Best regions for retirement