9 Towns in Massachusetts that Are Ideal for Seniors

Ranked the best state in the country for quality of life, the Bay State should feature in the retirement plans of every senior citizen. And for those who take the quality of medical care seriously, something every retiree should, the state where the Pilgrims first landed provides a top-notch experience. According to The Commonwealth Fund, for instance, Massachusetts boasts the best overall healthcare system in the United States. Besides, seniors retiring here will be delighted to learn that Massachusetts exempts Social Security retirement benefits and income from public pension funds from taxation. Needless to add, the state’s breathtaking coastline and gorgeous islands could just beat any anti-aging product for their life-giving flair. Discover nine towns in Massachusetts that are ideal for seniors.

Chatham

No adjectives can possibly describe the experience of retiring in a maritime haven that comprises pristine sandy beaches, tidal shoals, several miles of saltwater inlets, and that provides access to gorgeous barrier islands. Incorporated in 1712, Chatham is older than the United States by several decades. A walkable downtown. Quiet neighborhoods. Beachfront mansions. Seafood-serving restaurants (Check out The Chatham Squire). Several medical facilities in the Cape Cod area. These — and more – are what Chatham offers. The town has a median age of 67, meaning retirees will be part of a relatable community of peers and associates. For outdoor adventure, Monomoy National Wildlife Refuge is a birdwatcher’s paradise.

Lexington

For retirees who have the barest interest in American history, Lexington provides an experience few other towns can match. Here is where Paul Revere, best known for his midnight ride to warn the colonial militia about the approach of British forces, played a role in scenes that eventually marked the first armed conflict of the American Revolution. Retirement life can consist of exploring historic sites such as Lexington Green (where the first battle between the Minutemen and the Redcoats took place), Buckman Tavern (where Sam Adams was almost captured when the British reached Lexington), and Hancock-Clarke House (where Paul Revere stopped on his celebrated midnight ride). Seniors will love the fact that Lexington is just about 20 miles from Boston and its cultural attractions, is reassuringly safe, and features a social demographic where about 1 in 3 is a senior.

Williamstown

As a retiree, the last thing you will want is some obscure town with no intellectual culture. As medical experts have always advised, reading through one’s lifetime improves brain functioning and can help delay certain neurodegenerative disorders, including Alzheimer's disease. Fortunately Williamstown — because it hosts Williams College — one of the oldest colleges in the country, is a college town that prides itself in its high intellectual culture. But here is the exciting part: Local residents, under certain conditions, can audit courses completely free of charge. Besides, every afternoon, you will want to enjoy golfing at the Taconic Golf Club, probably with a college professor you have befriended, while discussing Shakespeare’s Hamlet, Much Ado About Nothing, or Julius Caesar. If you still crave some mental diet, the Clark Art Institute will leave you blown away.

Northampton

Northampton is a suburb of Springfield (only about 21 miles separate the two towns) and hence, is known to provide convenient access to terrific shopping malls such as Five Town Plaza, excellent medical facilities such as Mercy Medical Center, and other senior-friendly amenities. Nestled in the picture-perfect foothills of the Berkshire Mountains, in a region that is part of the famed Five Colleges Community, Northampton, just like Williamstown, will see one’s mind consistently engaged and active. Seniors, those aged 55 years and above, make up about 31% of the town’s population. This means empty-nesters will get to arrange fireside chats with similarly-aged hometown buddies. At the Smith College Botanic Garden, colorful flower shows are known to enliven the experience of residents while Norwottuck Rail Trail is a great outdoor environment for walkers and bikers of all ages, including seniors.

Dennis Port

For starters, Dennis Public Library, one of the best in the region, comes with a genealogy room where residents can access ancestry, family search databases, and many more. For those who love water-themed adventures, something that humans are known to be fond of right from childhood, Denis Port is on the South coast of Cape Cod and hence, provides access to several Nantucket Sound beaches. Sea Street Beach, for instance,  segmented by short, cute little jetties, is enticingly tranquil in the off-peak seasons — while sea shells-laden West Dennis Beach — is often a beautiful place to catch a sunset. But here is what could be the most exciting part: Seniors make up about an impressive 50% of the population in Denisport. This means every second person in Denis Port is an empty nester with whom you can have intimate conversations. Finally, the Pelham House Resort will come in handy if seeking a venue for a romantic wedding anniversary.

Wayland

Both Stacker and Niche have ranked Wayland among the 100 Best Small Towns to Raise a Family in the U.S. But that is not enough. This Massachusetts secret has also been recognized as among the most desirable to live in the United States. When it comes to safety, Wayland particularly scores big. Safewise, for instance, ranked it as the safest city in Massachusetts in 2023. For perspective, Wayland reported zero violent crimes and an equal number of property crimes in the reporting year. Located just 20 miles from Boston, Wayland is minutes away from a town that digital healthcare company Medbelle has previously named as having the best hospitals in the United States and second-best in the world.

Brewster

Nickerson State Park, which spans a massive 1,900 acres, is a Brewster staple that seniors will take a liking to, especially those who want to play with the air, hike the scenic trails (to keep their muscles from loosening up), or pitch a tent in the woods — amid the twinkling of the stars and the luminescence of the moon. Plus, the Cape Cod Rail Trail, a paved rail trail that runs through six Cape Cod towns, passes through Brewster — and can make for an awesome pastime. Boasting a median age of 62.8, retiring in Brewster involves associating with people in the same age bracket, implying meaningful social support and networks. Expect a sparse, suburban environment here, where a whopping 84% of the residents are homeowners. The icing here is that seniors make up about 53% of Brewster's population.

Manchester-by-the-Sea

Forget about the movie of the same name — and one of the best-written movies of 2016.  Manchester-by-the-Sea is in the rocks-laden peninsula of Cape Ann, a beautiful expanse named for Queen Anne, the wife of the British King James I. Quaint old fishing villages, including those that make up Machester-by-the-Sea, are among this area’s best-known features. According to Niche, 76% of Manchester-by-the-Sea residents are homeowners, a factor that lends credence to the town’s retirement appeal, while a heartening 39% (approximately) are fellow seniors aged 55 years and above. Moreover, those with a master’s degree or higher make up 34% of the town’s population, meaning the regular guy down the street may know one or two about Leo Tolstoy, The First Amendment, or Vincent van Gogh. Often ranked among the wealthiest towns in the state, expect a bucolic, upscale environment, where finesse and elegance float in the very air. Finally, retiring here means one will be approximately 30 miles from Boston.

Sandwich

About 2,800 residents call this Massachusetts treasure, one of the first that welcomes visitors to Cape Cod, home. Sandwich is reputed to be the oldest town on the Cape and is best known for the glassware produced in the area in the 19th century — a story best relived at the Sandwich Glass Museum. Named for its seaport counterpart in Kent, England, Sandwich boasts fairy-tale beaches, including Town Neck Beach, a pretty beach with a fantastic boardwalk that provides tasty views of the vast grasslands right by the seashore. Then again, besides being an excellent camping site, the Shawme-Crowell State Forest offers wonderful outdoor opportunities — and can make for a perfect second home. 90% of Sandwich’s residents are homeowners, implying virtually everyone here is keen on making this gem his or her permanent abode. Finally, seniors comprise an impressive 44% of the town’s population, implying the chance to vibe with a similarly-aged crowd.

The Takeaway

If seeking a retirement spot, there are several factors that qualify Massachusetts for consideration. And it is not just about the heart-melting beauty of the state’s shoreline, quaint fishing villages, colonial settlements, or beautiful islands. The Bay State boasts the best overall healthcare system in the United States and is also ranked the best in the country for quality of life. When it comes to retirement towns, seniors will be spoilt for choice. Still, Chatham, Lexington, and Williamstown are often chart-toppers. Hot on their heels are other underappreciated retirement havens, including Northampton, Denis Port, and Wayland.