New England's Comfiest Retirement Destinations That Will Take Your Social Security Far

By the time President Franklin D. Roosevelt implemented the Social Security Act in the midst of the Great Depression, social welfare programs for the disabled and elderly had already found success in dozens of countries, including Denmark, France, and England. Now, the better part of a century later, Social Security's still intact, although it's regularly under threat and could even see massive cuts in the coming years, according to the Center on Budget and Policy Priorities. Depending on your age, when you retire, and overall earnings over your working life, you're eligible to receive monthly Social Security benefits that average just under $2,000, but can range anywhere from about $50 to upwards of $4,000.

As the cost of living continues to climb, however, and Social Security hasn't necessarily followed suit, it's becoming increasingly difficult to retire on these monthly checks alone. Although New England is often considered to be one of the country's most expensive regions, you'll still be able to find pockets where the cost of living is below the national or state average, where there are senior discounts on things like food and transportation, or where subsidized housing, tax cuts, or free programs for seniors are easily accessible to offset the average costs.

What's more, living in the Northeastern United States means you'll never be more than a short I-95 drive, plane ride, or Amtrak trip away from major cities like Boston and New York. Thanks to long-standing institutions like Yale New Haven Hospital and Tufts Medical Center in Boston, globally-ranked medical care is also within reach. After careful research into everything from grocery prices to scenic views and comfy amenities, we've selected nine New England destinations where your Social Security benefits will go far. 

About 90 miles from Boston and less than 30 miles from Hartford, Connecticut, you'll find Springfield, Massachusetts — a city home to approximately 155,000 people. The state doesn't tax Social Security or pension benefits. You'll also be eligible for Senior Circuit Breaker Tax Credit if you're over 65 — the amount, which can total up to $2,730, is determined by rent or property taxes. Older adults living in Springfield, specifically, have access to fitness classes, health screenings, and more at the Raymond A. Jordan Senior Center, and the city also offers senior discounts for trash pickup services. At the time of writing, the cost of living here was close to 25% below the state average, and nearly 4% lower than the national average.  

If you're planning to move to Springfield, keep in mind that one famous figure is key to the city's legacy: Dr. Seuss, author of children's books like "The Lorax" and "The Cat in the Hat." He was born in Springfield in 1904, and you'll still be able to find traces of him around town, especially at the Dr. Seuss Museum and the outdoor statue garden, which features some of the author's most famous characters carved in stone. Admission is free for residents. Around the holiday season, Springfield locals can look forward to Grinchmas activities, which include jazz performances on the illuminated Quadrangle Green. The city is also home to the Basketball Hall of Fame, a weekly downtown farmers market from June to September, and dozens of restaurant options within walking distance of one another. Springfield is also anchored by two major medical centers: Baystate Health and Mercy Medical Center.

Similar to Springfield, Pittsfield's Massachusetts location means that Social Security isn't taxed, and you'll also be eligible for a Senior Circuit Breaker Tax Credit. The city is in the heart of the Berkshires and known for its buzzing, artsy vibe despite its relatively small size. In the fall, when leaves turn vibrant shades of red, orange, and yellow, visitors drive in from out of state to check out the scenic views. There's a Halloween parade downtown, a tradition that's been going strong since the 1940s, and residents are even encouraged to hand-make the floats. In many ways, with its quaint New England cottages, collection of small businesses, and independent theaters, Pittsfield feels like a step back in time.

Beyond its cozy, small-town charm, one of Pittsfield's main appeals for retirees is its comparative affordability: Overall, the cost of living here is 26% lower than the state average at the time of writing. Capital Square Apartments also offers subsidized housing options to older adults. At Ralph J. Froio Senior Center, right across the street, you'll have access to things like discounted breakfasts and lunches at the Box Office Café, fitness classes, tech workshops, and more. There are revolving exhibits at the Lichtenstein Center for the Arts downtown, free live music on the first Fridays of the month, and new developments on North Street and the Upstreet Cultural District. If you need access to the amenities of a larger city, Albany, New York, is a 40-mile drive away, and Berkshire Medical Center offers both emergency and specialized care.

New Hampshire is often ranked among the best states to retire in the U.S. thanks to its tax advantages. Concord, which is New Hampshire's third-largest city after Manchester and Nashua, is particularly popular for its blend of historic charm and nature. You'll find an old-fashioned, cozy Main Street lined with taverns, small kitchen supply stores, and florists. In some ways, not much has changed here over the last 100 years or so. You can still check out books from the New Hampshire State Library, which was built in 1895, explore the grounds around the state house, where there's a farmers' market on Saturday mornings from May to October, and walk alongside the Merrimack River, once used to water-power textile mills.

"The downtown is like a community living room," says realtor and Concord resident Ryan Hvizda on YouTube while also highlighting the city's more than 80 miles of trails. "Within a mile of walking through the neighborhoods, I'm in wild forest," she added. Other picturesque outdoor spaces include Rollins Park and Terrill Park, popular for picnicking, and the Audubon, which leads bird-watching expeditions, nature talks, and even a book club. Adults 55 or older can qualify for subsidized apartments at Horshoe Pond Place, helping Social Security checks go further. On average, however, the rent for a one-bedroom apartment is under $1,500, which is more than $100 less than the national average, and seniors have access to discounts on meals, local entertainment, and outdoor attractions across the city. 

New Hampshire has several financial advantages that set it apart. Namely, there's no sales tax in the "Granite State," which has resulted in an abundance of outlet stores, a few of which are located just outside Manchester. There's also no tax on Social Security, which has attracted a sizable retirement-aged population. In fact, 20% of New Hampshire residents are 65 or older, making it the state with the second-oldest population after Maine. Over all cost of living in Manchester is still over 11% higher than the national average. However, housing costs in Manchester are still considered relatively affordable when compared to other areas, but you'll want to invest quickly, because it's also a rapidly expanding market. You'll also find comparatively affordable grocery prices in New Hampshire, per World Population Review, which can also help take your Social Security check even further.

When it comes to health needs, institutions like Catholic Medical Center and Elliot Hospital are a short trip away, but there are also world-renowned facilities in Boston, which is a little over 50 miles from the city. Perhaps one of the most attractive things about Manchester is its landscape: The city's downtown sits alongside the Merrimack River, and there are plenty of hiking and recreational trails in the area if you like to stay active. You'll also be able to explore destinations like the Currier Art Museum, which has free admission days, and the Zimmerman House, a Frank Lloyd Wright creation from 1950. In the spring, attend a Fisher Cats game, or escape cold weather on a plane from Manchester's underrated regional airport, which offers cheap flights to dozens of destinations.

In Maine, residents over the age of 65 are eligible to receive property tax relief, and there's no tax on Social Security income here, either. Benefits like these have made the state attractive to retirees. In fact, Maine has the oldest population in the country, according to the State Economist, and more than 23% of its residents are over the age of 65. Houlton, Maine, in particular, is known for its affordability. At the time of writing, the median value for a single-family home was approximately $150,000, just over $200,000 below the national median. Market Square Commons, a downtown apartment complex, rents one- and two-bedroom affordable housing units to residents 55 and up. If you choose to live here, you'll be able to connect with fellow Mainers in the community rooms or the building's library.

Houlton's quiet, Victorian-era downtown right alongside the Canadian border gives it a cozy feeling, almost like you're traveling into a bygone age: The streets are lined with brick buildings, and there aren't many big box stores or chains. The community's also considered relatively walkable; you'll be able to bounce between quaint grocery stores selling locally-sourced products, small-town bakeries like Sadie's on Water Street, and the historic Temple Theatre, a cinema which screens new releases. The public library downtown helps residents set up telehealth appointments, and Houlton Regional Hospital is a nearby option for in-person medical care.

Before choosing to retire in Houlton, keep in mind that you'll be about as far north as you can get before hitting Canada, so expect single-digit temperature lows come winter. You'll also need to drive about an hour north to hop aboard a commercial flight at Presque Isle International Airport.

The cost of living in Lewiston, Maine is 6% higher than the national average but 5% lower than the state average. However, there are also subsidized senior housing options if you're 65 or older. For those looking to buy, the median value of a single-family home here is around $250,000, which is less than the aforementioned national median. Portland, Maine's largest city, is about 40 miles away, but Lewiston has all the amenities you might need. Hospitals like St. Mary's and Central Maine Medical Center anchor the city, and Bates College, where you can attend hockey games, lecture series, or visit the art museum, keeps the community vibrant. 

SeniorsPlus, a local nonprofit, offers free fitness classes, knitting groups, and Medicare advice for older adults. You can also reserve Around Town Café Restaurant Vouchers to receive discounted meals from local restaurants. Outdoor enthusiasts only need to travel 2 miles from the heart of downtown to find Thorncrag Sanctuary. There's picnic space, walking trails (some of which end in scenic views of Mount Washington), and bird-watching areas. One of Lewiston's most famous events is the annual hot air balloon festival in August, which includes live music, an artisan market, and even tethered balloon rides over Simard Payne Park.

Wallingford sometimes fondly referred to as "Wallyworld," has been named one of the best places in New England to retire, per finance publisher Kilpinger, thanks to its relative affordability compared to other areas in Connecticut (though the cost of living is still about 13% higher than the national average) and proximity to major cities like Boston, which is about 125 miles north, and New York, 90 miles south. Plus, there's a brand-new affordable housing complex in the works, which will make that Connecticut zip code even more accessible.

From the center of town, it also doesn't take long to reach Yale New Haven Hospital, Connecticut's top-rated hospital, and there's specialty healthcare available at Gaylord Hospital nearby. Wallingford Senior Center, meanwhile, has a regular list of activities on the docket: You can join the monthly hiking group, practice your swing on the pickleball club, or even take part in overnight bus trips to destinations like Mackinac Island. The senior center's onsite cafe offers discounted meals, and volunteers can help you apply for state or federal benefits as needed. If you don't have access to your own car, make sure you call ahead of time to reserve free transportation services to the grocery store or doctors' appointments. 

There's plenty to do downtown, especially if you're an enjoyer of craft beer or locally-made cider. Make sure to try out New England Cider Company and Center Street Brewing Company, or drive to the outskirts of town to sample a few reds and whites at Paradise Hills Vineyard and Winery, which also hosts live music and book clubs. What's often considered to be one of America's best apple orchards is just outside of Wallingford, too. Explore the corn or sunflower mazes, or stop by to pick peaches and blueberries in the summer.

The cost of living in Hartford is 6% lower than the state average of Connecticut. What's more, according to 2025 data on Homes.com, housing here falls below the national median, too. Seniors in Hartford have access to 10 to 15% discounts on groceries, fast food orders, UPS services, oil changes, and much, much more, which will take your monthly Social Security benefits further. 

Overall, the city has a lot in common with Wallingford, Connecticut, which is just 25 miles away. For starters, it also offers top-rated medical care through Yale, UConn Health, and Hartford Hospital, closer to town, easy access to major cities, and a vibrant, walkable downtown. According to recent census data, the number of older adults in Hartford now exceeds the number of children. Consequently, the area, extending into West Hartford, is hoping to update its infrastructure to support its growing population of retirees, adopting plans for at-home medical care, scheduling tech classes, and offering more social groups for seniors in "third spaces." 

Hartford has multiple senior centers that offer a range of services; at NorthEnd Senior Center, for instance, you can save money with the help of congregate meals, mobile foodshare programs, or onsite health screenings. Monthly fees are only $20. Perhaps Hartford's most attractive quality, however, is its access to transit: The Hartford Line Commuter Rail connects the city to New Haven, and Bradley International Airport is only about 20 miles away from the heart of downtown. If you're a homebody, not to worry: there's plenty to do closer to town, like America's oldest public rose garden, the Mark Twain House Museum, or the Wadsworth Atheneum Museum of Art. 

Although the cost of living is 5% higher than the national average, Montpelier is 2% less expensive than the state average and considered to be one of the most affordable cities in Vermont by AD Mortgage. The capital city will offer all the scenic views and cozy comfort the state is known for. Take a peaceful journey through Vermont's past at Green Mountain Cemetery, where hills turn fiery shades in the fall, stop by the gold-domed capital buildings, nestled into a hillside, or see how maple syrup is made at Bragg Farm. Annual dues are $25 at the Montpelier Senior Activity Center, but you'll be granted access to a variety of events and services. There's tax preparation help, ukulele classes, and a weekly community meal if you're hoping to save money. You can also see if you qualify for rental assistance through the Montpelier Housing Authority. Tenants are expected to pay approximately 30% of their income toward rent and utilities at options like Lane Shop Apartments or Prospect Place.

Montpelier also has a walkable downtown. You can hop between gelato shops, bookstores, and bistros, or shop at the Capital City Farmers Market, which heads inside when the weather gets cold. There's an active live music scene, along with numerous annual events like WinterFest and Mayfest, most of which are free of charge. Nearby healthcare options include the Central Vermont Medical Center, part of the University of Vermont Health Network. Burlington International Airport is 35 miles away and offers direct flights to plenty of warmer destinations in the winter.

Given that the cost of living is continuing to increase in the United States, it's also becoming harder and harder to retire on Social Security alone. That's why we searched for cities where housing costs were below the national average, below the state average, or places where subsidized housing was an option to offset the costs. Also important to consider were local senior discounts, which can mean saving on groceries, entertainment, or even oil changes. Because access to medical care is key to aging safely, we prioritized cities close to major hospitals or healthcare complexes. Since New England is one of the most expensive regions of the United States, some places are technically above the national average for cost of living but meet other criteria, so we decided to include them.

In curating the most comprehensive list possible, we also looked for communities that had active downtowns or senior centers with busy calendars. "Number one [to aging well] is the overwhelming importance of being socially connected and engaged," Dr. John Rowe, a professor of health policy and aging, told the Columbia University Irving Medical Center, adding, "Study after study indicates that this is critically important." Especially if you're new to an area, it's best to have multiple avenues through which you can make new friends. Of the senior centers we featured, multiple offered meal vouchers, foodshare programs, or even wellness screenings to help members save money. 

Featuring firsthand accounts was also important to us, so we consulted Realtor vlogs, Nextdoor comments, and Reddit to gauge whether our data was reflected by public sentiments. If you didn't see a town you were expecting to see on this list, make sure you check out our breakdown of the best New England towns for retirees looking for scenery and simplicity.