The charming town of Provincetown, Massachusetts.

7 Most Inviting Towns In Massachusetts

Massachusetts, the Bay State of some seven million residents, is tiny—just over 10,500 square miles—but how scenic! Among the most popular places to visit in New England, it bathes in a seascape of hospitality, bursting with good vibes at the seams and sprinkling charms on all the curious and hungry for nautical vibes.

Its inviting towns, most excited to welcome new visitors, introduce the best sides of the enchanting state with experiences for every taste. Duxbury is all about oystering, Sandwich is the oldest town on Cape Cod, and Stockbridge's very famous native is... well, you can learn about it at the Norman Rockwell Museum of Art, housing the world's largest collection of his paintings and illustrations.


The shoreline of Duxbury, Massachusetts
The shoreline of Duxbury, Massachusetts.

Inviting you with open arms, the sweet town of Duxbury, some 34 miles south of Boston, is a favorite getaway from the city and into its scenic embrace, serene charm, and generous attractions. Home to just over 15,000, the hospitable residents happily share the beauty of everyday life, from the beautiful historic homes to the spectacular Duxbury Beach Park. As pleasant as it sounds, the state park offers immersive natural experiences along varying, perfectly strollable trails, wildlife picnics, and a dreamy beach at low tide in the summer.

All about oystering, Duxbury takes visitors on a delightful journey of discovering its craft for an anytime getaway, from delicious seafood restaurants like the casual Raw Bar or the Winsor House for fine dining, both at Island Creek Oyster Farm to a wonderful boat excursion around the farm with insights into this thriving industry. The King Caesar House, a historical site and museum, as well as the Art Complex Museum, diversify the attraction scene. Savour the escape, and the town will cater to make every experience memorable, including the apt French Memories cafe and bakery or the haunted tavern Island Creek Oyster Bar for fresh oysters over a choice of drinks overlooking Duxbury Bay.


Aerial view of Newburyport, Massachusetts.
Aerial view of Newburyport, Massachusetts.

This town with a name that rolls off the tongue like honey and resonates with a childhood memory really does feel picture book-like. Just 50 miles from Boston, Newburyport's streets are steeped with nostalgia and architecture, dating back to its first founding during the Revolutionary War. An important stop on the Underground Railroad and soon gaining tourist appeal, little has changed since then to experience a coastal escape for every taste. With contemporary and old-fashioned attractions for every taste wrapped up in coastal landscapes, escape the city hustle into the welcoming change and feel the shoulder tension melt as you let go of the worries against the endless deep sea views to the horizon. Bursting with New England charm, from whale watching to traditional hospitality and the loveliest boardwalk on a stroll, the nautical scenery is enchanting.

The riverfront Cashman Park features a nautical-themed playground and a boat launch, and if you squint, the Plum Island Lighthouse will wink back at you. Take the trail from its cute ice cream parlors to the beach or along the picturesque Federal-style houses on the High Street thoroughfare, while State Street is a shopping promenade with unique places for antiques to decorate your home, bring a gift or treat yourself to a brand-name item. Home to some 18,000 people, the town at the crossroads of the Merrimack River and the sea beckons the water babies into the summertime outdoors with beaches and scenic trails through the Parker River National Wildlife Refuge.


Downtown Northampton, Massachusetts.
Downtown Northampton, Massachusetts. Editorial credit: EQRoy /

Northampton, the county seat, invites visitors to get away in style along the beautiful western shores of the Connecticut River. Nestled in Western Massachusetts’s Pioneer Valley, some 19 miles north of Springfield, the atmosphere is charged with intellectual stimulation. Truly a quintessential New England town, it is a bohemian mecca for creatives, dubbed "Paradise City," and with local hospitality, you can experience all the perks. Attracting artists and musicians, Northampton's burgeoning arts scene and colorful streets give off a distinctive Nottingham Hill vibe, particularly the significant historic Elm Street/Round Hill District with its many 19th and 20th century properties from the mid-19th to early 20th. Drenched in nostalgia, put the camera at rest and soak in every inch on a stroll.

Home to Smith College and many academics and authors who balance out the "hippy" side, Northampton is the heart of the Five-College Area, replete with cultural activities, much thanks to the top-ranked private liberal arts women's college. Visitors can browse many inviting bookstores, farmers markets like the Thornes Marketplace downtown, and local talent through the years at the Museum of Art. Enjoy an attractive botanic garden on a relaxing stroll while the students enjoy studying along the lush river banks and recreational parks like Frank Newhall Look Memorial Park and Childs Park. Home to the Northampton Independent Film Festival, LGBT Pride, and an annual Springfest, for the evening, the welcoming local breweries bustle with good vibes, and the Academy of Music is the only municipally owned theatre in the US.


Aerial view of Provincetown, Massachusetts
Aerial view of Provincetown, Massachusetts.

Tipping the peninsula, Provincetown is a nation renowned for its all-inclusive, inviting atmosphere. Unfathomably striking the balance as a family favorite seaside escape and a gay resort with a large LBGTQ population, this pet-friendly town is also highly regarded in historical circles for being the original landing place of the Mayflower, which is, not coincidentally, the state's flower. Charming with genuine hospitality, visitors report feeling at home on a retreat with many attractions for each taste. Overlooking the beach, Race Point Lighthouse, an active 1816 structure, may be open for tours, with lodging in its nearby historic buildings.

Drenched in New England vibes and coastal scenery, Race Point Beach ranks among the region's best with its soft sands and towering dunes that attract photographers and are so much fun to climb, while the popular Dune Shacks Trail, is a beautiful hike to the ocean through a melange of windswept sands, some tree growth, and a stone boardwalk. Whether you're in for lounging beachside or to explore the celebrated architecture and upscale shops along Commercial Street, the town bathes you in New England charms, including historic sites and fine dining. The revered Pilgrim Monument and Museum is a literally unmissable 252-foot granite monument to the Mayflower Pilgrims with dramatic city and harbor views.


Dexter's Grist Mill in Sandwich, Massachusetts.
Dexter's Grist Mill in Sandwich, Massachusetts. Editorial credit: LEE SNIDER PHOTO IMAGES /

The British, who fell in love with the views overlooking Cape Cod Bay, settled in this angelic town, Cape Cod’s oldest, in 1637 in the southeast corner of the present-day state. Imitating Kent's village of Sandwich in England, the historic town embraces an impressive architectural landscape of colonial buildings like Hoxie House, Wing Fort House, and Sandwich Friends (Quaker) Meetinghouse. Immediately east of Bourne along the bay's shore, Sandwich flaunts the most impeccable beaches, like Town Neck Beach, with clear waters lapping pristine sands. Don't miss the Dexter Grist Mill and Green Briar Nature Centre & Jam Kitchen on your outdoor wanderings.

Sandwich is also home to the Cape Cod Canal Visitor Centre, while its Heritage Museums & Gardens, Sandwich Glass Museum, and restaurants along the canal showcase the town's multifaceted talents. The Scusset Beach State Reserve sprawls across the canal with its sweeping bay vistas, while for some quality time in nature with your loved ones, a hike to a picnic spot through the serene Shawme-Crowell State Forest can't be beaten. The inviting 1,350-foot-long Sandwich boardwalk beckons with seaside views and attractions—think carnival food that's easy to munch on the sands between the beautiful marshes and Cape Cod Bay.


The serene town of Stockbridge, Massachusetts
The serene town of Stockbridge, Massachusetts. Image credit: Joe Mabel via Wikimedia Commons.

This Berkshires town of barely 2,000 year-round residents hosts an inviting atmosphere for all tourists seeking cultural enrichment at its one and only Norman Rockwell Museum. Featuring the largest collection of the town native's art in the world, many of his paintings and illustrations depict the idyllic surrounding landscapes and bucolic life in Stockbridge. Tiny and tucked near the New York border, visitors can enjoy easy access from Boston and feel eons away from the city. Before the famous American painter, the town was settled in 1734 by British missionaries on a mission to convert the indigenous Stockbridge Indians, quickly spinning out as an art colony and soon a tourist destination thanks to the rolling Berkshire Hills of Western Massachusetts and the river setting.

Nestled along the lush Housatonic River banks and named after a Hampshire town in England, Stockbridge transports you overseas along its colorful Main Street with countless specialty shops, art galleries, and boutique stores. Also home to the sculptor Daniel Chester French, Chesterwood is his home and studio, while the Berkshire Theatre Group offers plays for the evening. Among the cute eateries and Gilded Age mansions, the standouts include Merwin House and Lenox Station Museum. Visitors can enjoy strolls through Berkshire Botanical Garden and Naumkeag Mansion & Gardens, while Red Lion Inn offers a stay in history. In the summer, join the locals at "Stockbridge Bowl" Lake Mahkeenac, or seek serenity along recreational trails like the Mary V. Flynn Trail, Laura’s Tower Trail, and Ice Glen Trail.


 Williamstown, Massachusetts
Aerial view of the Thompson Memorial Chapel on the campus of Williams College in Williamstown, Massachusetts.Editorial credit: pics721 /

This picturesque mountain town in the beautiful Berkshires of western Massachusetts feels like a cozy hug. Embracing visitors, Williamstown's striking balance of hospitality and natural beauty strikes through the heart, so foreign to city souls, and feels like a getaway in the faraway Alps. From outdoor activities for every level to cultural attractions, there are plenty of experiences under the watchful eye of Mt. Greylock, while MASS MoCA, a celebrated art museum and performance center, is minutes east in the neighboring town. The Housatonic River runs through Williamstown, taking you along its flow in a canoe or floating through lush scenery.

Locals enjoy quick access to nature, not to mention the countless trails, from easy ones like Hoosic Nature Trail and Spruces Park, with two stone lions at the entrance, to summiting the state's tallest peak via aesthetic paths with spectacular vistas. Offering a towering backdrop for a memento during your downtown strolls and browsing through local shops and eateries, don't miss the hit Water Street Grill, while Clark Art Institute attracts visitors from near and far for its admirable collection of European and American art. Nearby, the teaching Williams College Museum of Art College offers free public admission to its large American modernist collection, which pretty much sums up the genuine spirit of this town in the Bay State.

Simply magical, escape the bustle of Boston or even the hustle of New York with easy access to these oceanside gems. From charming seaside villas to the Berkshires steeped in history, every town is spoiled with nature and most flaunt English names, christened after the settlers' hometowns. Provincetown's all-inclusive atmosphere is world-famous, while Northampton gives off distinct Notting Hill vibes, and Newburyport has that picture-book feel with a coastal story you can be the author of.

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