Top 10 Most Beautiful Small Towns in Massachusetts, USA

Best towns in Massachusetts

Like any other major city, Boston is considered the best place to visit in Massachusetts. But if your trip allows, there are many other small towns throughout the state, each offering something a little different.

If you like beaches and ocean views, stop in towns like Newburyport and Marblehead. Or take the ferry to Provincetown at the tip of Cape Cod or Martha’s Vineyard or Nantucket Islands for a day trip. On a beautiful fall day, head west to the Berkshires to photograph the foliage or hike one of the many trails.

The list of small towns to visit in Massachusetts could go on and on, but for now you may find a few favorites to explore.

Edgartown, Martha’s Vineyard.

The islands of Nantucket and Martha’s Vineyard are popular destinations in Massachusetts because they are easily accessible by ferry from Cape Cod. Among them are several small towns that are particularly pleasant to visit – one of them is Edgartown on Martha’s Vineyard. It was a famous whaling port back in the 1800s and still retains its period charm. The charming downtown is filled with boutiques, art galleries and restaurants, including Seafood Shanty, Alchemy and Vineyard Scoops (a must for ice cream). Regardless of which part of the island you’re staying in, make sure you have a bike on hand, as it can be a good and convenient way to get to the local beaches and town. Also, be sure to check out Oak Bluffs and Vineyard Haven if you find yourself in Martha’s Vineyard.


Address Marblehead, Massachusetts, USA Route online Visit website

Marblehead is a picturesque, quaint coastal town just 16 miles north of Boston that offers mostly bed and breakfast options. If you want a boutique hotel atmosphere, choose the Marblehead Hotel, which still preserves the city’s history and offers modern amenities in a 14-room hotel. Of course, when visiting a place like Marblehead, you’ll want to visit one of the local beaches – in this case, Devereux and Preston beaches are ideal options. If you want to dine out, check out 5 Corners Kitchen, Casa Mia, Little Harbour Lobster Company or Three Cod Tavern.


In northern Massachusetts, near the southern border of New Hampshire, is another coastal town, Newburyport. This historic town dates back to 1635, though today it’s mostly visited for its waterfront restaurants and quaint downtown filled with local boutiques and other stores. If you’re in the area in warm weather, drive to Plum Island and spend a day at the beach or take a walk on the Sandy Point State Reservation.

Provincetown, Cape Cod

Address Provincetown, Massachusetts, USA Route online Visit website

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You can’t go wrong with any of the small towns that make up Cape Cod, but if you head all the way to the tip of the peninsula, you’ll end up in Provincetown, known among locals as “P-Town. ” The town is known for its gay culture and art galleries, as well as great restaurants, stores, beautiful beaches and lighthouses along the Cape Cod National Seashore. Their annual Pride festival is called the Provincetown Carnival and attracts many crowds and festivities.

It’s also worth noting that Provincetown is quite dog-friendly: resorts like the Surfside Inn allow four-legged friends to stay overnight. P-Town is accessible by car, of course, but can also be reached by ferry from Boston.


Salem is known as the site of the Salem Witch Trials and is a great place to visit during the Halloween season, as this is the time of year when the annual Salem Hauntings take place, with plenty to do for the whole family. More recently, Salem has also introduced the Holiday Happenings festival from late November through the beginning of the New Year. But no matter what time of year it is, you can go on a variety of spooky tours or explore on your own and learn all about the history of this city. And when you’re choosing where to stay, check out the historic Hawthorne Hotel or the Salem Hotel, owned by Lark Hotels.


Address Scituate, Massachusetts, USA Route online Visit the website

If you’re looking for a small beach town less than an hour from the city (give or take taking into account traffic, depending on the time of year!), Head to Scituate, located on the south shore of Massachusetts. Here you’ll find beautiful beaches – Humarock, Maynott and Peggotty, among others – as well as several coastal restaurants, including Riva Restaurant & Bar, Oro and Lucky Finn Café.

There aren’t many places to stay in Scituate, but that may be part of its beauty as it doesn’t have a touristy atmosphere. If renting a house isn’t for you, try The Inn at Scituate Harbour or visit Cohasset Harbour Resort or Red Lion Inn. During the summer months, all types of accommodations will be booked in advance, so plan accordingly, especially if you’re in town for an event on a particular weekend.

If you want a taste of the South Shore by staying a little closer to town, another option is Hingham.


Address Stockbridge, Massachusetts, USA Get directions

Stockbridge is one of the many towns to visit in the Massachusetts Berkshires just west of Boston. From music festivals and art galleries to historic homes and trains, you’ll find all kinds of activities here, perfect for hiking, biking, snowshoeing, and more.

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The area is beautiful any time of year, but especially during the fall foliage season, when the leaves change color and create perfect scenes wherever you look. Stockbridge is home to the Norman Rockwell Museum, which houses his work, and another special place to visit is the Berkshire Botanical Gardens.

There are plenty of hotels and bed and breakfasts to stay in, as well as more luxurious options such as Cranwell Resort or Canyon Ranch Lenox, the latter of which is actually not far from Stockbridge, about a 10-minute drive away.

The 10 most charming towns in Massachusetts

The 10 most charming towns in Massachusetts

The 10 most charming towns in Massachusetts

Video: USA_40 Boston, Massachusetts. Harvard University 2022, Sept.

Often overshadowed by its larger neighbor New York, Massachusetts is a true American gem. While it is full of vivid memories of American history, they are balanced by a trendy, modern flattery of contemporary culture that embraces originality by focusing on communities. Traveling through this small state offers plenty to do, including strolling the chic streets, hiking mountain trails and sailing in the beautiful Atlantic Ocean.



Sometimes called “America’s hometown,” Plymouth is a city steeped in history, from its conception when the Pilgrims landed on its shores in 1620 to establish one of its first colonies. It then expanded into rope making, shipbuilding and fishing, but its most popular industry now is tourism. It has many sites that attract visitors from all walks of life, especially in commemoration of America’s first Thanksgiving. The monument at Plymouth Rock marks a place that holds a special place in the collective memory of the United States, as does a replica of the Mayflower, the ship in which the Pilgrims were landed. Plimoth Plantation is one of the most popular sites because it is a living museum, dotted with the wooden huts of the original colonial settlement.

Plimoth Plantation, Plymouth, MA 02360



The quintessential Massachusetts town is a peaceful gem lined with brick facades, old Victorian houses, and small cobblestone streets. Harvard Square, the soul of this town, is almost always bustling, mostly with students, as people hop between bookstores and small cafes. You can often find musicians peddling or artists selling their work on the streets. As scenic as Harvard University, with its stretched lawns and old-fashioned buildings, this is not the only site worth visiting in this city. The Massachusetts Institute of Technology is also in Cambridge, as is nearby Central Square, which has a street full of unorthodox restaurants and stores that reflect the non-conformist atmosphere of this city.

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Harvard Square, Cambridge, MA 02138



Wellesley is the archetypal town of Massachusetts. With a population of nearly 30,000, it is famous for its education, visible in the number of students it has because of the several colleges in the area. It has cute streets lined with small houses and stores, as well as inviting natural settings. Wellesley College is a sight to behold in its own right, as its sprawling campus mixes with old and modern buildings and is very green, full of trees and other vegetation. Babson College is also attractive. Wellesley, in fact, has a lot to offer if you like being outside, as there are more than 25 miles of trails that twist through town and neighboring woods, passing hills and through several reservations in the area. There are greenhouses, an arboretum and the home of the Massachusetts Horticultural Society. But it’s also a proud town that, like many in Massachusetts, has its own unique series of stores, including Wasik’s Cheese Shop, Wellesley’s Books and Blue Ginger Restaurant, all cherished by locals and visitors.

Massachusetts Horticultural Society, Wellesley, MA 02482

Forest Hole

Located on southern Cape Cod, this tiny town, technically part of larger Falmouth, makes for a very rewarding visit. It expands in the summertime as residents with vacation homes wave off the previous cold months to swim in the beautiful water. In fact, the Atlantic coast is the most stunning part of this town, the beaches are long and golden and the water is a stunning blue. Because of its proximity and good ocean conditions, Woods Hole has many centers and aquariums dedicated to marine biology and oceanography, making it the perfect place to experience different types of marine life. When you’re not swimming, visitors should check out the quaint stores and activities in town, including folk dance nights at the hostel. Or, if you’re looking for more, take the stunning bike path along the coast leading to Falmouth, which has a larger selection of unique stores and places, and a ferry that brings people to the popular Martha’s Vineyard Island.

Martha’s Vineyard, Duke County, Mass.



With three colleges, including the Greater Massachusetts University, Amherst is home to more than 80 percent of the student body. This concentration of students makes for an interesting dynamic in the city. The area is known for its political activism and leftist leanings, and downtown Amherst is full of students and fun places, from organic restaurants to bakeries to liberal bookstores. The town also has a rich literary history, as Robert Frost taught in the area, and Emily Dickinson, one of the most famous poets in the United States, lived in Amherst all her life. Her home has become a museum open to the public and is well worth a visit. You should also take a look at UMass Amherst’s WEB Du Bois Library, the tallest university library in the world because of its collection and its enormous size. Just outside of town, you can experience rural Massachusetts, with its lush green surroundings.

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Emily Dickinson Museum, Amherst, MA 01002



The people of this Bay Area have an enduring history of left-wing politics and acceptance that is showcased in the interactive and fascinating Freedom Trail, which leads visitors and residents throughout the city to see all of its sights and attractions. Boston’s role as one of the first urban areas in the U.S. on the water is evident in its multiculturalism; don’t miss checking out the vibrant North End, home to many Italian immigrants, or Chinatown, both of which have delightful bakeries and ethnic restaurants. Those looking for a more alternative atmosphere should visit Jamaica Plane, a more bohemian and diverse neighborhood, or SoWa in Boston’s south end, famous for its markets, stores and art galleries. Boston Bay is also a necessary stop, as is Prudentis, Boston’s tallest building and shopping center. Stroll down Newbury Street, the trendiest street lined with picturesque brick buildings, and see old-fashioned mansions on the water.

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Concord is a Massachusetts town with a national reputation for its important place in American history. The battles of Lexington and Concord were fought here, sparks for the American Revolution, which were later heavily romanticized by propaganda and patriotic myth. Concord has an even greater literary history. It was a hotbed of transcendentalist thought and literature in the nineteenth century; Ralph Waldo Emerson was at the center of a prominent group of authors, including Louise May Olcott, Henry Thoreau, and Nathaniel Hawthorne. Their work can be found today in the rustic and cozy wooden library, which boasts a small transcendentalist wing. Visitors should also take a trip to Walden Pond, where Thoreau coolly lived in a cabin for two years to write his book Walden. It’s a relaxing walk along the townhouses and New England nature, including the river that runs through the area.

Concord Free Public Library, Concord, MA 01742



Provincetown, known by many as the “P-town,” is a hot tourist destination that nonetheless retains its unique identity after decades of building itself as a cultural nucleus in the area. It’s no surprise that visitors at the very top of Cape Cod visit the seductive beaches, whether it’s a cold walk in the winter or a crowded sunbathing session in the summer. What makes this town unique is its strong artistic flair, with a variety of art galleries and craft stores, as well as centers that promote fine art and writing, and the Provincetown International Film Festival, served by independent films. Provincetown is also well known for its large LGBTQ community, especially in the summertime. You shouldn’t miss visiting The Atlantic House, the world’s oldest gay bar since 1950, and discreetly partying even longer, which has a history of catering to intellectuals and other literati.

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Salem, seen by many as a haunted house in the United States, is a medium-sized town on the North Shore of Massachusetts, its strategic location on the coast making it one of America’s most important seaports. Its fame is largely due to the Salem Witch Trials, which consisted of trials and executions of accused witches in the late 1600s because of widespread paranoia in the area. Salem took advantage of this fame to generate revenue from tourist sites such as the Witch House, which tells the story of the trials and their context. Because of this reputation, Salem is also very busy around Halloween, and fall in general, as crowds graze to take advantage of the festival spirit and action while admiring the beautiful colors of the season. Salem is also an attractive place throughout the rest of the year. Its wooden colonial houses provide a picturesque backdrop, and the Peabody Essex Museum, one of the oldest in the country, is also recognized as one of the best for its large and growing collection of art and libraries.

Witch House, Salem, MA 01970


Greater Barrington

The Smithsonian listed this town of less than 10,000 as the best small town in America. It is located in the Berkshires, a privileged vacation area in far western Massachusetts. Residents take pride in its beauty, especially the Taconic Mountains, which are a spectacular part of the Appalachian Mountains. It has recently become an Appalachian Trail community, making it an ideal stop for nature lovers who can relax by walking down quaint Main Street, especially in the spring when it is lined with flowering trees. Greater Barrington also offers visitors the opportunity to see one of the “castles” of the United States, Searles Castle. This beautiful and towering structure sits in the middle of the woods and was intended as a home modeled after the romantic French castle style. This town was also the original home of the famous American intellectual WEB Du Bois, to whom the National Historic Landmark is thus dedicated in its childhood home.

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