For the 50+ Traveler
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Quaint fishing villages, gorgeous seaside enclaves, historic towns, and scenic hamlets dot the Massachusetts landscape. From the tip of Cape Cod to the top of the Berkshires, the getaway options are diverse and intriguing.

Here are 11 of the best small towns to visit in the Bay State.

The harbor of Edgartown, Massachusetts.

1. Edgartown

Martha’s Vineyard embodies a maritime atmosphere at every turn. The seaport village of Edgartown charms visitors with its historic homes, pristine beaches, and peaceful oases.

Walk along Main Street and the Water Streets to take in the quaint seaside cottages and turn-of-the-century homes that create a sense of refined, quiet luxury.

Afterward, stroll down to South Beach. Located on the southern side of town, it boasts free parking and great surf. It is a perfect place to relax and soak up the glorious sunshine.

Chappaquiddick is a local favorite and is accessible via a short ferry ride. If you are searching for a quiet spot to kick back and let the day float by, Chappaquiddick is the place to be. Relax on the beach, walk along the shore, or kayak your way to Vineyard zen.

2. Nantucket

Nantucket, Massachusetts’s other vacation island, shares its name with the town of Nantucket. This postcard-perfect town is just the ticket for a relaxing, toes-in-the-sand getaway.

Cisco Brewers is the place to see and be seen on the island. Everyone eventually makes their way to Bartlett Farm Road for a pint or two. It’s a fun spot to sneak a peek at the steady stream of vacationing celebrities and holiday revelers.

Plan on watching the sunset on Madaket Beach. The scene is breathtakingly beautiful and not to be missed. Parking can be tricky, but there are plenty of taxi and rideshare options on the island, making cars virtually unnecessary.

Beach views of Provincetown, Massachusetts.

3. Provincetown

Cape Cod is Massachusetts’s most famous beach playground, and Provincetown should be at the top of your must-visit list. Located at the tip of the Cape, Provincetown is a quick ferry ride from Boston.

Provincetown is home to the oldest continuous art colony in America, and you will encounter fine art galleries throughout the village. A haven for the LGBTQ+ community, Provincetown welcomes all visitors with open arms and good times.

Stroll down Commercial Street for a dizzying array of restaurant options. The Landing Bistro & Bar serves up locally sourced, handcrafted menu items. Stop by the Provincetown Fudge Factory for a vacation dessert to satisfy your sweet tooth.

There is always a party going on in Provincetown. Check the town’s extensive festival calendar before you visit.

4. Chatham

From uber-chic experiences to dive bar fun, Chatham offers visitors shopping, great eats, and a main street made for an afternoon stroll.

Bask in luxury at the Chatham Bars Inn. The inn is a sought-after vacation venue because of its amazing location, classic Cape Cod architecture, and first-class service. Book one of their spa suites or a luxurious cottage along their private beach. Dining options include everything from catered picnics on the beach to private dinner parties and everything in between. Alternatively, you can simply order a glass of prosecco, sip it on the front porch, and people-watch.

In town, stop by The Chatham Squire for lunch. The Squire is a local haunt where the walls are covered in discarded license plates, the food is authentic, and the conversation is engaging.

Parking on Main Street is limited, but there is a large lot with free parking at the Chatham Town Hall.

Autumn in the quaint town of Stockbridge, Massachusetts.

5. Stockbridge

Stockbridge is the quintessential New England woodland town. Located in the Berkshires, it is home to the Norman Rockwell Museum and several estates including Chesterwood and Naumkeag.

Iconic American images from the covers of The Saturday Evening Post come to life at the Norman Rockwell Museum. View Rockwell’s work in addition to other exhibits at this treasured museum.

Stockbridge’s sprawling estates bring history to life as you stroll the grounds and explore the homes. Chesterwood is American sculptor Daniel Chester French’s home. French is best known for crafting the figure of Abraham Lincoln for the Lincoln Memorial. Naumkeag is the summer estate of Joseph Hodges Choate, former ambassador to Great Britain. It offers a variety of events, including tours, yoga, and art classes.

6. Sturbridge

A stop at The Publick House for a pint in the historic taproom, dinner at Ebenezer’s Tavern, or a night at one of four lodging options will help you discover the history and beauty of Sturbridge.

Old Sturbridge Village is a working village representing life in New England in the 1830s. The costumed historians bring the area’s heritage to life. Armed with period tools of the trade and the stories of their ancestors, the staff educate and inspire the young and young at heart.

Antiquing is more than a hobby in the Berkshires -- it’s a way of life. Check out Sturbridge Antique Shops, a collaborative comprising more than 75 different dealers.

The deCordova Sculpture Park in Lincoln, Massachusetts.

7. Lincoln

Lincoln is a small Massachusetts town where art, farming, and history come together harmoniously.

Stroll the deCordova Sculpture Park and Museum to view stunning contemporary art installations on the expansive grounds. The indoor galleries offer unique and exciting modern art exhibits.

At the Drumlin Farm Wildlife Sanctuary, you can take a quiet walk through a working farm, where sheep, goats, cows, pigs, and chickens graze. It’s a wonderful place to spend a few hours, especially if you have youngsters in tow.

The Minute Man National Historical Park visitor center is also located in Lincoln. At this center highlighting the battlefields of the American Revolution, you can learn about Paul Revere’s famous ride and plan your visit to the park. Minute Man National Historical Park is spread over three towns: Lincoln, Concord, and Lexington.

8. Concord

Scenic downtown Concord begs you to linger and enjoy the interesting little shops and cafes. Antique shops grace old wooden storefronts that show years of well-maintained wear.

The Minute Man National Historical Park in Concord covers the Battle Road Trail and the North Bridge, where “the shot heard round the world” began the American Revolution.

The Minute Man statue in Concord marks the spot where the first colonial militia men were killed. The sculptor was Daniel Chester French of Stockbridge.

Henry David Thoreau’s Walden Pond is also located in Concord. The Walden Pond Path is an easy 1.7-mile loop with beautiful views.

Aerial view of Manchester-By-The-Sea, Massachusetts.

9. Manchester-By-The-Sea

Of the many towns on Massachusetts’s gorgeous North Shore, three are standouts. One of these is Manchester-by-the-Sea, the setting of the 2016 movie of the same name starring Casey Affleck. The town is on Cape Ann and boasts gorgeous beaches, spectacular homes, and plenty of Atlantic seaside charm.

Singing Beach is a small public beach best known for its singing sand. It is believed that the singing is caused by the wind blowing through the beach's unique sand. In certain conditions, the singing sound seems to be caused by just walking in the sand.

Manchester-by-the-Sea is only 34 miles from Boston, making it the perfect place for a day trip.

10. Rockport

Also on Cape Ann, Rockport is home to the famous Motif No. 1. Artists flock to the area in an attempt to capture its natural waterfront beauty. For art lovers, this translates to more than 30 art galleries in the small town. The walk along Main Street and Bearskin Neck to the harbor is lined with shops, galleries, and restaurants for your enjoyment.

Parking is limited and expensive in downtown Rockport. You can park in the Blue Gate Lane lot for free and hop onto the shuttle to town for a small fee.

Aerial view of Newburyport, Massachusetts.

11. Newburyport

If you love old brick marketplaces, scenic harbors, and beachy islands, Newburyport is for you.

Newburyport’s Market Square Historic District is lined with brownstone shops where you can search for one-of-a-kind finds.

Plum Island is a small vacation resort and wildlife sanctuary. Rent a cottage for a long weekend or a full week if you can. Plum Island’s relaxed vibe will wash over you like a curling ocean wave.

A required stop for lobster aficionados is Bob Lobster, where you can indulge in lobster poutine or a fried lobster dinner. Dine outside at the picnic tables, enjoying one of the finest lobster feasts around.

Planning a getaway to a picturesque little town in Massachusetts is a must when visiting Boston. Each town’s unique flavor changes with the distinct Massachusetts seasons.

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