
Massachusetts may not be the sunniest or the cheapest place to retire; however, this underappreciated treasure has a lot to offer retirees. There are also many places to retire in Massachusetts, so you can choose the location that suits you best.
Of course, there are a few less favorable aspects of Massachusetts too, which often come to the forefront of our minds when considering retirement in the Bay State.
First, the average cost of housing is close to twice as much as the national average, with Cape Cod being one of the most expensive areas in the U.S. However, parts of western Massachusetts are far more affordable.
Second, the taxes here are higher than in other areas in the country; however, they are in line with other states on the east coast. Social Security and public pensions are not taxed, but all other retirement income is subject to being taxed.
Additionally, sales tax is 6.25%, but there is no local or county sales tax. And there are some tax exemptions on essentials such as prescriptions, clothing under $175, and groceries.
For retirees who qualify, there is a real estate tax called the circuit breaker credit, which is available to residents who are 65+ and meet the other outlined criteria around their income and value of their home.
Finally, retirees not used to the snow and cold may find Massachusetts’ winters challenging. However, retirees who enjoy winter activities such as skiing and snowshoeing will be right at home in the Bay State.
Now for the many benefits of retiring in Massachusetts, most notably, the state’s vibrant art and history culture. A significant contributor to the state’s art culture comes from its diverse population and many colleges.
Massachusetts is home to several festivals that celebrate the arts, like Williamstown Theatre Festival, Jacob’s Pillow Dance Festival, and the Tanglewood Music Festival. Plus, there are numerous galleries, theaters, and museums throughout the state, especially in Boston.
The colleges and universities found in Massachusetts are world-renowned. Retirees looking to continue their education will love the many opportunities available like the Five College Learning in Retirement program or Harvard’s Institute for Learning in Retirement, which is open to all seniors.
Another major draw for seniors is the top-rated healthcare facilities. Massachusetts has some of the world’s best medical centers, like Massachusetts General and Tufts Medical Center.
Of course, outdoor and active retirees will find the mountains, ocean, and many rivers very appealing. There is an abundance of things to do year-round here, such as hiking, camping, fishing, downhill skiing, and more. And many of the smaller towns are walkable (much like Newark in New Jersey), allowing retirees to get around on foot instead of driving everywhere.
And these are just a few of the Bay State’s benefits, read on to learn more about the top retirement cities and see which one is the best option for you.

Where to Retire in Massachusetts
- Boston
- Springfield
- Cambridge
- Northampton
- Rockport
Boston

Percent of Senior Population: 11.5%
Overall Population: 692,600
According to Bankrate, Boston is one of the best cities to live and retire in. Boston has a strong economy, exceptional educational opportunities, and top-notch health care facilities, all of which aid in the city’s appeal.
Boston is known for its abundance of art and culture opportunities and its historical significance in our country’s history. Those looking to live in an urban area full of museums, galleries, and theaters will adore living in Boston.
Some of the top museums and sites history buffs will want to see include:
- Boston Tea Party Ship Museum
- USS Constitution Museum
- John F. Kennedy Presidential Library and Museum
- Boston’s Freedom Trail
- Bunker Hill Monument
Plus, there are many art venues like the Museum of Fine Arts, Boston Theater, Boch Center, Citizens Bank Opera House, The Wilbur, and Symphony Hall.

Boston also draws the attention of active retirees. The city is very walkable, so seniors looking to spend more time on foot than behind the wheel of a car will love the convenience this city has to offer. Moreover, the 2,300 acres of parks in the town are perfect when looking to spend more time in nature.
Besides being within walking distance to most amenities, Boston has an excellent mass transit system, including city buses, subway systems, commuter rail, and the ferry.
Of course, the city has more than its share of medical centers, including world-class hospitals like Massachusetts General Hospital, Harvard Medical School, and the Dana-Farber Cancer Institute.
Springfield

Percent of Senior Population: 12.6%
Overall Population: 153,606
Springfield sits along the shores of the Connecticut River in the southwest region of the state. This is a city of diversity and community, combining urban amenities with small town charm.
Often referred to as the city of firsts, Springfield has many claims to fame such as being:
- The birthplace of Dr. Seuss, which is honored by The Amazing World of Dr. Seuss Museum.
- The city where basketball was invented, which is celebrated at the Basketball Hall of Fame
- The location George Washington chose for the National Armory, which is historically recognized by the Springfield Armory National Historic Site.
Springfield is also home to the Springfield Museum featuring art, history, science, as well as the Titanic Museum.

In addition to the city’s museum scene, Springfield offers various cuisine options, including high-end five-star restaurants to cozy cafes, and everything in between.
Springfield has several parks like North Riverfront Park, Forest Park, and Van Horn Park for retirees looking for outdoor activities. Bicyclists, walkers, and joggers will love taking advantage of The Connecticut River Walk and Bikeway, which stretches 3.7 miles. And if you are looking to get out of town, you can head to the southern Vermont mountains, which are less a two hours away.
Adding to the city’s overall appeal is the average cost of houses in Springfield is cheaper than both the national and state average, coming in around $200,294, according to Zillow.
And Springfield has ample medical care available, including Bay State Medical Center and Mercy Medical Center.
Cambridge

Percent of Senior Population: 11.1%
Overall Population: 118,927
Cambridge has fondly been referred to as the “intellectual capital of the world” because it is home to Harvard University and Massachusetts Institute of Technology (MIT).
The two higher learning institutes have several benefits for the residents of Cambridge. For example, they add a lot to the art and culture scene, including 20 Harvard museums and several MIT museums.
There are several local parks that the residents enjoy visiting. Plus, the local cemetery, Mount Auburn Cemetery, attracts bird watchers and history buffs. The cemetery is a National Landmark full of manicured gardens and is an important bird area since it is also a wildlife sanctuary.

Plus, the Charles River Bike Path extends over 20 miles and starts at the Museum of Science. This asphalt multi-use trail and is enjoyed by walkers, inline skaters, runners, and cyclists.
Like most college towns, Cambridge is very walkable and allows residents easy access to the city’s amenities on foot. The city also has a diverse culinary scene and lively nightlife.
Plus, if you want to head to the big city, downtown Boston is just five minutes away, allowing you access to top entertainment venues like the opera, broadway, and symphony. And though Cambridge is close to Boston, its crime rate is lower than the national average.
The quality of medical care in Cambridge is some of the best you can find in the country, if not the world.
Northampton

Percent of Senior Population: 18%
Overall Population: 28,451
Like many of the Massachusetts cities, Northampton is another intellectual mecca being home to five different colleges. Best of all, retirees can enjoy continued education through the Five College Learning in Retirement program that gives retirees access to workshops and seminars.
Northampton also has a variety of entertainment and cultural venues like:
- Academy of Music
- Calvin Theater
- Sage Hall
- Smith College Museum of Art
- Serious Play Theatre Ensemble
In addition to museums and theaters, Northampton hosts various festivals like The Northampton Independent Film Festival, Biannual Paradise City Arts Festival, and The Paradise City Arts Festival.

Active retirees can enjoy touring the picturesque campuses or one of the several local parks and gardens, including the Botanic Garden of Smith College and Mass Audubon Arcadia Wildlife Sanctuary, which has wonderful walking paths and picnic areas.
And Northampton is a hub on the rail-trail system. And when finished, this rail to trail will be 104 miles long from Northampton to Boston. It is a multi-use trail dotted with small towns full of fun stops like restaurants, breweries, and boutiques.
When residents want to get in some shopping or find a great place to eat, they head over to Thornes Marketplace. The marketplace is full of specialty stores like the Olive Oil Company, Heavenly Chocolate, Booklink, and more. Thornes also hosts a spa and yoga studio.
Plus, retirees will love the low crime rate and high quality easily accessible medical care.
Rockport

Percent of Senior Population: 33.7%
Overall Population: 7,282
Rockport is a small seaside town located on the Cape Ann peninsula’s tip and is very appealing to outdoor enthusiasts, especially those who want to spend time on the water. Being a seaside town, Rockport is perfect for kayaking, sailboating, and fishing.
But water activities aren’t the only way to enjoy the outdoors in Rockport; Halibut Point State Park is just a short drive from downtown and is the ideal spot for hiking and fishing in the summer and cross-country skiing in the winter. Those who enjoy biking can spend time off-roading on their mountain bike or taking in the sites on paved paths. If you don’t own a bicycle, you can always rent one in town.

Rockport is a tourist town with several boutiques, specialty stores, and antique shops to spend an afternoon. And since Rockport is home to several artists, it is not surprising that the town boasts upwards of 30 galleries featuring work from more than 400 unique artists.
The downtown area also features casual dining, breweries, and cafes. Plus, there are several indulgence options like the fudgery and ice cream shop. And if you are dining in Rockport, you better like lobster since Rockport is in the heart of the lobster country.
There are also live performance venues in town like the Shalin Liu Center, which sits on the beach with a backdrop of the ocean. Or retirees can take in a musical at the Shore Music Theater, which has put on several performances every year, including the Music Man, Christmas Carol, and the Little Shop of Horrors.
Unfortunately, this small town does not have a hospital within city limits. The nearest hospital is just shy of a 1/2 hour drive away in Gloucester.
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