6 Great Places to Retire in New England

Middletown, Conn.

• City population: 46,747
• Share of population 65+: 14.4%
• Cost of living for retirees: 19.2% above the national average*
• Average income for population 65+: n/a
• Community score: 59.8*
• State's tax rating for retirees: Least Tax Friendly (opens in new tab)

Like much of the Northeast, Connecticut is known to be a high-cost area, and Middletown is no exception. But the Hartford metro area, of which Middletown is a part, is at least more affordable than other major metro areas in the state, including Stamford and New Haven, according to the Council for Community and Economic Research. And local residents tend to pull in high enough incomes to make it work. The city's average income for all households is $90,977 a year, and it's even better for the older population with incomes for residents age 60 and up averaging $92,851 a year.

Plus, being home to Wesleyan University, Middletown offers all the benefits of retiring to a college town, including numerous restaurants, shops and cultural attractions. You can also take advantage of the Wesleyan Institute for Lifelong Learning, which offers no-credit courses, lectures and other educational opportunities at minimal cost and is open to the entire community. And while the nearby city of Hartford has an alarmingly high crime rate—with 1,093.8 violent crimes per 100,000 residents reported, compared with the national rate of 473.2 for cities of similar size—Middletown is far safer with a mere 49 violent crimes total reported for the year.

*Data for the Hartford metropolitan statistical area, which includes Middletown.

Portland, Maine

• City population: 66,715
• Share of population 65+: 13.7%
• Cost of living for retirees: 17.1% above the national average
• Average income for population 65+: $44,769
• Community score: 65.8
• State's tax rating for retirees: Mixed (opens in new tab)

The largest city in Maine, Portland offers a lively downtown and plenty of urban-esque amenities amidst the great outdoors of the Pine Tree State. You can enjoy museums, theaters and an array of eclectic dining. The flagship L.L. Bean store in nearby Freeport is a must-see for many visitors, but resident shoppers also flock to Portland’s unique boutiques and outlets.

All the while, you’re never too far from the area's many beaches. That means ample opportunity to lounge on the shore or dive into water-based activities including fishing, kayaking, sailing and even surfing. And of course, hiking and biking trails abound—perfect in the (much) colder months, too, for cross-country skiing and snowshoeing.

Pittsfield, Mass.

• City population: 43,289
• Share of population 65+: 19.0%
• Cost of living for retirees: 7.9% above the national average
• Average income for population 65+: $58,231
• Community score: n/a
• State's tax rating for retirees: Not Tax Friendly (opens in new tab)

New England is notoriously expensive, but Pittsfield, located in the western part of Massachusetts, offers a small pocket of relative affordability—more reasonably priced than Boston and Cambridge, where living costs are, respectively, 48.1% and 38.1% above the U.S. average. Housing is notably affordable: The median home value in the city is $173,200, compared with $407,400 for all of Massachusetts and $592,300 for Boston proper, according to Zillow.

Leaf peeping in the fall may be enough to draw you to the Berkshires. But you have plenty to enjoy all year round, including excellent sites for camping, fishing, hiking and skiing. Nearby, enjoy musical performances at the Tanglewood Music Center, the summer home of the Boston Symphony Orchestra. There’s also world-class art at the Clark Art Institute in Williamstown and the Massachusetts Museum of Contemporary Art (MASS MoCa, for short) in North Adams.

Laconia, N.H.

• City population: 16,237
• Share of population 65+: 20.5%
• Cost of living for retirees: n/a
• Average income for population 65+: n/a
• Community score: n/a
• State's tax rating for retirees: Most Tax Friendly (opens in new tab)

Tiny Laconia offers a big bargain for your retirement destination. The overall cost of living is 1.2% below the national average, according to Sperling's BestPlaces, making it much more affordable than Manchester—about 50 miles south—where living costs are 13.2% above average. But local average incomes are still high, averaging $71,605 for residents across all ages. That adds up to favorable odds for a balanced budget. And the Granite State's tax situation for retirees is solid, too.

Tucked between Lake Winnipesaukee and Winnisquam Lake, Laconia has been dubbed "The City on the Lake," home city to New Hampshire's Lakes Region. That means plenty of beaches and water-related activities for you in the warmer months. Other outdoor recreation abounds nearby, too. Gunstock Mountain Resort in neighboring Gilford, for example, offers camping, ziplining and snow sports, as well as fairs, events and dining options. Local crime may be worth noting: While the state sports a low rate of 1.99 violent crimes per 1,000 residents, Laconia's rate is 4.68, even slightly higher than the national median of 4 violent crimes per 1,000 residents, according to NeighborhoodScout.com. On the bright side, between 2009 and 2018, there have been only two murders in town, according to the community's police department. The site lists Parade Road-Old North Main Street and Weirs Beach-Lakeport as the safest neighborhoods in Laconia.

Providence, R.I.

• City population: 179,509
• Share of population 65+: 9.6%
• Cost of living for retirees: 21.9% above the national average
• Average income for population 65+: $64,657
• Community score: 59.3
• State's tax rating for retirees: Not Tax Friendly (opens in new tab)

Home to Ivy League Brown University and the world-renowned Rhode Island School of Design, as well as a handful of other colleges, Providence can be a great fit for retired intellectuals and artists. They'll have no shortage of things to do, with the schools offering gallery nights, performing arts events, educational opportunities and more. And the schools' presence has helped draw a variety of restaurants and businesses to the area, too.

Unfortunately, living costs and an unfriendly tax environment can be prohibitive throughout the tiny state, and Providence is no exception.

Burlington, Vt.

• City population: 42,453
• Share of population 65+: 10.7%
• Cost of living for retirees: 16.4% above the national average
• Average income for population 65+: n/a
• Community score: 64.2
• State's tax rating for retirees: Least Tax Friendly (opens in new tab)

This small mountain city on the shores of Lake Champlain is a picturesque setting for tree-hugging retirees. Outdoor recreation is plentiful with miles of hiking and biking paths, nearby beaches where you can swim, kayak or paddleboard in the warmer months, and numerous skiing options in the area. An eco-friendly vibe permeates the town, from the businesses bolstering the city's economy, such as household-products maker Seventh Generation, to the local food movement feeding the neighborhood.

But being green isn't easy on your wallet. Taxes and living costs are high. While the median home value is a low $206,000 in the Green Mountain State, compared with the median $229,000 for the U.S., it climbs to $326,500 in Burlington. A private room in a metro area nursing home costs a median $11,498 a month, compared with $8,365 a month for the U.S. At least you can save money on academic pursuits. The University of Vermont will cover tuition costs for state residents age 65 and older who wish to take a class, even if it's for credit.

How We Picked the 50 Best Places to Retire

To pinpoint one great retirement destination in each state, we weighed a number of factors:

• Cost of living for retirees for major metropolitan and micropolitan statistical areas, with data provided by the Council for Community and Economic Research, includes overall costs, housing, food and groceries, transportation, utilities, health care and miscellaneous expenses.
• Household incomes, poverty rates and number of health care facilities are from the U.S. Census Bureau.
• Community well-being and physical well-being scores are provided by digital health company Sharecare, in collaboration with Gallup. These are two of the five elements of well-being that make up the overall Gallup-Sharecare Well-Being Index. (The other three elements are purpose, social and financial well-being.) The index is calculated on a scale of 0 to 100 and based on more than 2.5 million nationally representative surveys. Community well-being is defined as "liking where you live, feeling safe and having pride in your community." Physical well-being is "having good health and enough energy to get things done daily." We display the community score for each place we chose.
• Population data, including the percentage of the population that is age 65 and older, is also provided by the Census Bureau. The figures are highlighted in these rankings for the benefit of readers, but were not factors in our methodology for ranking the best places to retire.
• Taxes on retirees, based on Kiplinger's Retiree Tax Map (opens in new tab), which divides states into five categories: Most Tax Friendly, Tax Friendly, Mixed, Not Tax Friendly and Least Tax Friendly. This information is provided for the benefit of readers but was not factored into our selections within each state.