Best Cities Near Boston and All Around Massachusetts for Retirement

The Commonwealth of Massachusetts, affectionately known as the Bay State, is full of American history! It’s home to Harvard, the Pilgrim settlement of Plymouth, MIT, and more! Cranberries and turkeys can be found by the dozens and Fenway Park hosts the Boston Red Sox.

Compared to the rest of the US, Massachusetts’ cost of living is around 27.2% higher than the national average (according to Best Places). It has a population of nearly 7 million people. And, of that number, over 17% are aged 65 years and older.

Rockport

Just 25 miles outside of Boston, the scenic port town of Rockport is surrounded on three sides by the Atlantic Ocean. Rockport has many beautiful, rocky beaches and ships that go out in search of lobster. One interesting site to see is the Paper House. It’s made entirely of paper, including the home and home furnishings! Rockport is a place for seniors who are into art!

Concord

Nestled just outside of Boston, Concord is known as the hometown of many famous people in American history, such as Louisa May Alcott, Henry David Thoreau, and Ralph Waldo Emerson. Paul Revere performed his midnight ride that began the American Revolution through this city. Concord infrastructure still appears similar to older American history. Historical tours and homes in Concord will keep retired history buffs busy!

Newburyport

Newburyport is about 35 miles outside of Boston and is a beautiful Coastal town. Newburyport’s appeal is mostly in the many water activities like sailing and visits to Plum Islands. There is a Coast Guard station that’ss near by which aids in overseeing any seaport activity. Newburyport has a variety of recreational trails for residents and tourists. This town is vibrant and perfect for active senior adults!

Gloucester

Gloucester is situated on Massachusetts’ North Shore. It’s a nice seaside town, whose appeal is marine activities and lifestyle. Gloucester is famous for its seafood! Visit the Gloucester House for a waterfront dining experience!

Ipswich

If you love seafood and enjoy dining out, then Ispwich is the place for you. Ispwich is famous for its clams! In fact, much of the tourism of this town is related to clams. There’s an annual clam festival that draws scores of crowds.

Marblehead

The town of Marblehead is reachable by Boston transportation, but still has the small town feel that many people want. The town of Marblehead is the host to the Marblehead Neck Wildlife Sanctuary. Seniors and retirees who enjoy nature will love living near a sanctuary that hosts many wild animals that are free to live among the beautiful scenery. Marblehead is also the city that boasts the birth of the United States Navy. Marblehead’s main appeal for seniors may be the yatching. Yatching as well as commercial fishing is one of the best shoreline activities of Marblehead. Marblehead is a great town for seniors who would like to live in a community with sea activities. Marblehead may also be great for senior communities of friends who are interested in spending their retirement leisure time living in a beautiful small town.

Nantucket

The historic island of Nantucket is well worth the day trip to see the historic charm of the old whaling community. The streets are made of cobblestone and the buildings exude 19th century architecture. Majestic homes line the streets and there are literally miles of beach access and bicycle paths. The area is a wonderful place to shop with the family or stroll along the paths that lead to popular historical sites.

Stockbridge

Stockbridge is best known for its Main Street depicted in one of Norman Rockwell’s famous paintings. The community is rich in history and architecture dating back to the19th century. Large mansions sit above the streets featuring stories from the French and Indian Wars. The architecturally sound homes have housed rich farmers, aspiring artists and even some unassuming politicians throughout the years. Stockbridge is as full of history as it is mystery and is a wonderful place to visit in Massachusetts.

Provincetown

Near Cape Cod and along the farthest tip of the Cape’s curl is the exquisite community of Provincetown.The history dates back nearly 400 years and is home to the largest bohemian community in the state. Artists, writers and culture-mongers from all over the country visit Provincetown for its delicious food, retail therapy, and people-watching. One thing is certain in Provincetown– you will never grow bored.

Oak Bluffs

Located near Martha’s Vineyard, Oak Bluffs is one of those towns you don’t want to pass by without visiting. Kids, parents and grandparents find fun and lots of ice cream in this island harbor community. The streets along Circuit Avenue are filled with colorful cottages that lead to Mad Martha’s ice cream parlor and the beautiful carousel. Bike paths, beaches with public access and some of the best nightlife in the Vineyard can all be found in Oak Bluffs.