Massachusetts's 9 Best Retirement Towns Ranked

Massachusetts is a great choice for retirees seeking a vibrant and picturesque place to spend their golden years. With its rich history, charming small towns, and access to top-notch healthcare, the Bay State offers an ideal blend of cultural engagement and relaxation. From inland gems to coastal retreats, each town on this list has been selected based on its scenic beauty, quality healthcare facilities, reputable retirement communities, and opportunities for recreational and social activities. Whether you’re drawn to natural scenery, historic landmarks, or a close-knit community, these nine Massachusetts towns provide an outstanding quality of life for retirees aiming to enjoy a fulfilling and peaceful retirement.

Chatham

This cozy fishing town of fewer than 7,000 residents is known for its beautiful beaches and vibrant Main Street, lined with shops, restaurants, and buildings dating back to the mid-1800s. When it comes to healthcare, Chatham has got you covered. The Broad Reach Healthcare Campus offers services, including outpatient care, rehabilitation, hospice care, and extended services. Meanwhile, the Cape Cod Health Cardiovascular Center offers an array of cardiovascular treatments, including minimally invasive procedures. Among the varied options for senior living communities are Liberty Commons Nursing & Rehab and Victorian Assisted Living. Visit the Monomoy National Wildlife Refuge for tranquil bird-watching; stop by the Atwood Museum to discover an extensive collection of artifacts portraying life on the Cape since the seventeenth century; or take a tour of the 48-foot-tall Chatham Lighthouse, which was established in 1808.

North Falmouth

North Falmouth is a quaint town with a welcoming community, offering beautiful beaches and outdoor recreational activities. With more than 90 percent of its medical staff Board-certified, Falmouth Hospital includes everything from a cutting-edge cardiovascular procedure lab and women’s health center to a cancer center, ensuring that all your care needs are met. For premier assisted living and memory care, Atria Woodbriar Park is set on a 15-acre campus with all-inclusive amenities and discreet support available 24/7. Want to explore the outdoors? The 10.7-mile Shining Sea Bikeway is the only bikeway on Cape Cod that runs alongside the sea, affording great views across open water, barrier beaches, and salt marshes. Browse the shops and bookstores on Main Street before stopping for picture-perfect views of Martha’s Vineyard and Vineyard Sound from the Nobska Lighthouse. Be sure to check out the white picket fence surrounding Falmouth’s historic Village Green, where Colonial militia members practiced in the 1700s and around which sea captains constructed their homes.

Manchester-by-the-Sea

If stellar coastal views and a rich history lie atop your list of musts, the charming seaside town of Manchester-by-the-Sea merits consideration. Located within 10 miles of the town is Addison Gilbert Hospital. Winner of the 2024 Leapfrog Top Hospital Award for Outstanding Quality and Safety, this 79-bed medical acute care facility offers cancer care, pain management, emergency medicine, and more. Nearby is the Seacoast Nursing and Rehabilitation Center, which delivers both short-term rehabilitation and long-term care in a supportive setting. Brush up on the area’s history at the Manchester-by-the-Sea Museum which, housed in the 1823 Abigail Hooper Trask House, includes interesting exhibits, restored period rooms, and artwork. Masconomo Park features a community bandstand with an annual summer concert series. In addition, live food and music make Festival by the Sea a popular draw in August.

Orleans

Retirees will very much enjoy all that Orleans, a beautiful and safe town situated along Cape Cod, has to offer. Settled in 1693 by Pilgrims from the Plymouth Colony, the town was finally officially incorporated in 1797. It takes its name from Louis Philippe II, Duke of Orléans, who steadfastly supported the colonies during the American Revolution. A key contributor to the town’s growth was Isaac Snow, who fought in the Revolutionary War and later served as an instructor to the Orleans Militia during the War of 1812. Less than a half hour away is Cape Cod Hospital, which has been nationally recognized for exceptional care and is accredited by the American Association of Blood Banks, the Joint Commission, and the College of American Pathologists. The Terraces Orleans, opened in 1969, provides skilled nursing and independent living services. Feeling a little cooped up? Unwind on Nauset Beach, catch a show at the Academy of Performing Arts, or explore fine art at the Addison Art Gallery.

Stockbridge

Incorporated in 1739 and named for Stockbridge, Hampshire, England, this small town that lies along the Housatonic River in the Berkshire Hills essentially remained a Native American settlement until 1785. Experience internationally acclaimed music and dance festivals, historic homes and gardens, and impressive art galleries, all with the Berkshire countryside providing a spectacular backdrop. Back roads and trails abound for hiking, jogging, bird watching, and cycling. A National Historic Landmark, the Mission House is a rare surviving example of a colonial mission house. You can also check out the Federal-style Merwin House, which showcases the Merwin family’s extensive collection of American and European furnishings. Art enthusiasts will enjoy the Norman Rockwell Art Museum, where the painter’s original oil paintings are displayed. And you’ll have peace of mind knowing that Fairview Hospital, recognized as one of America’s Top Rural Hospitals and offering 24-hour emergency care, is nearby. Options for assisted living include Kimball Farms Nursing Care Center and Cameron House in nearby Lenox.

Brewster

Initially settled in 1659, the Town of Brewster is named after William Brewster, a Mayflower passenger in 1620 and the religious leader of Plymouth Colony. Brewster earned the nickname Cape Cod’s Sea Captains’ Town for the 50 or so sea captains who called the town home in the eighteenth and nineteenth centuries. Among the homes gracing the town is Cobb House, a 1799 structure that today houses the Brewster Historical Society and its six interactive exhibit galleries. What’s more, you can catch an enthralling performance at Cape Rep Theatre and browse a broad array of art galleries and antique shops. With recreational activities ranging from biking and hiking to boating and fishing, this place is an outdoor lover’s dream. Be sure to keep an eye out for year-round events hosted by the Cape Cod Museum of Natural History. Ideally situated near Brewster are Cape Cod Hospital and Maplewood at Brewster, which offers assisted living, independent living, respite care, and memory care.

Wellfleet

Up until the end of the American Revolution, Wellfleet was a thriving whaling port known for its abundance of oysters and fish. The Massachusetts Cultural Council designated Wellfleet’s town center and harbor as a Cultural District in 2017 in recognition of the vitality and concentration of its cultural, artistic, and natural resources. Spend some time exploring the town’s galleries, restaurants, and theaters before admiring phenomenal scenery at the 1,183-acre Wellfleet Bay Wildlife Sanctuary. The Wellfleet Health Center offers everything from primary care services like adult medicine and women’s health to behavioral care like psychiatry and psychology. Whether you’re interested in yoga or screenwriting, Wellfleet Preservation Hall offers many programs and activities throughout the year.

Yarmouth Port

With approximately 6,000 residents, Yarmouth Port makes another outstanding choice for retirees looking to escape the hustle and bustle of the city. With its convenient proximity to Cape Cod Hospital, everything from imaging services to gynecological care is just minutes away. Maplewood at Mayflower Place is among several senior living facilities available for short-term rehabilitation or long-term care. The town’s rich history, which you’ll learn about through engaging exhibits at the Historical Society of Old Yarmouth, stretches all the way back to 1639. Stroll along the boardwalk at Gray’s Beach, one of the most scenic spots in all of New England. The Edward Gorey House celebrates the life and legacy of American author and playwright Edward Gorey, preserving his works for future generations. The Captain Bangs Hallet House Museum is open seasonally, which reveals how sea captains' families lived in the Victorian era.

Northampton

Home to approximately 30,000 people, Northampton boasts a vibrant downtown and ample cultural diversity. It’s home to Cooley Dickinson Hospital, which is part of the Mass General Brigham healthcare system and provides comprehensive medical services. CareOne at Northampton is a 119-bed skilled nursing facility offering around-the-clock rehabilitation services and long-term care programs that are personalized to each individual patient. Northampton was known as Nonotuck, meaning “midst of the river,” by its original Pocumtuc inhabitants. Legend states that Northampton was named by John A. King, one of the first white settlers in Northampton, or possibly in King's honor since he was likely born in Northampton, England. In 1786, Daniel Shays and a group of Revolutionary War veterans stopped the civil court from sitting in Northampton in an uprising called Shays' Rebellion. A year later, members of the Northampton community were present at the Constitutional Convention in Philadelphia, where the U.S. Constitution was drawn up and ratified. Learn more about the area’s heritage through illuminating exhibits, projects, events, and programs at Historic Northampton. Among the area’s other great attractions are the Smith College Museum of Art, the Norwottuck Rail Trail, and Thornes Marketplace, home to over 25 independently owned shops and restaurants.

Treat Yourself To Tranquility In These Small Towns

As you can see, there’s a lot more to the Bay State than Boston. Retiring in Massachusetts means embracing a lifestyle that melds relaxation and natural beauty with cultural enrichment and excellent healthcare. Each of these nine towns offers retirees a unique atmosphere, whether it’s the charm of a historic downtown, the tranquility of the coast, or the striking beauty of New England’s countryside. With engaging community events, reputable retirement homes, and access to top medical facilities, these towns ensure that retirees can enjoy their later years with peace of mind and abundant opportunities for leisure and connection. No matter your preferences, Massachusetts has a scenic small town ready to usher you into a fulfilling, enjoyable retirement.