Retro sign in downtown of small town Newburyport, Massachussetts.

Massachusetts's Best Small Towns for a Weekend Escape

Massachusetts is a New England state in the northeastern U.S. with some of the best small towns to please weekend travelers needing an escape. With an abundance of things to see and do around commercial locales and natural or historical landmarks, there is no shortage of fun and enjoyment to be had while exploring and taking in new sights and communities. These towns may entice any weekender to stick around in the Commonwealth and never return home!

Oak Bluffs

Carpenter Gothic Cottages with Victorian style, gingerbread trim on Lake Avenue, Oak Bluffs on Martha's Vineyard, via Wangkun Jia /
CLake Avenue, Oak Bluffs on Martha's Vineyard, via Wangkun Jia /

Oak Bluffs is a small town on Martha's Vineyard with 5,284 residents who love indoor and outdoor attractions. At Martha's Vineyard Camp Meeting Association, weekend visitors can expect to find history and culture within an 1830s religious estate that remains a popular tourist site for its cottage paper umbrellas and community lantern events. Joseph Sylvia State Beach has two miles of sandy wave thrills and scenic beach vibes; it was also used as a key filming landmark for "Jaws"! At East Chop Lighthouse, weekenders can also check out some spectacular harborside views and enjoy sunsets around Vineyard Sound.

Park lovers may find a lot of excitement at Ocean Park, a downtown Victorian-era landmark with cute shopping goods and a fairytale ambiance. Pirate Adventures is also a wonderful option for anyone who loves treasure hunting along the historic shoreline! Tourists looking for quick bites while in town for the weekend can check out Back Door Donuts for delicious fritters and donut cravings or Offshore Ale Company for the finest rustic brew scenery. For lodging options, Oak Bluffs Inn is one of the best in town when it comes to memorable front porch vibrance and downtown amenities.


Newburyport at the mouth of the Merrimack River in Massachusetts.
Newburyport at the mouth of the Merrimack River in Massachusetts.

A coastal town of 19,020 inhabitants, Newburyport is great for weekend travelers who like being around notable landmarks. The Maudslay State Park is a 19th-century hotspot for nature lovers who want to see rolling meadows, lush gardens, and the largest mountain laurels in the state. The Joppa Flats Education Center is another option for anyone who wants to witness wildlife habitats up close at nature sanctuaries for the weekend, with rich birding history and "touch tanks" for a true bonding experience with marine life!

At the Custom House Maritime Museum, weekenders may love cultural heritage knowledge and local port history about the Merrimack River and the Industrial Revolution. Boardwalk fans may enjoy Waterfront Promenade Park, where grassy hills and riverside musical events are ideal for weekend amusement. Shoppers in town can check out Tannery Marketplace for friendly locals and lovely Thai dining options, while others can visit Oldies Vintage Marketplace for the coolest nostalgic trinkets! Anyone booking a stay in Newburyport can lodge at Clark Currier Inn for a charming New England fall beauty or Essex Street Inn & Suites for cozy fireplaces and quiet dining amenities.


Horse carriage at Sturbridge Village, MA,
Horse carriage at Sturbridge Village, MA.

A rural town of 2,232 locals, Sturbridge has everything a weekend needs for a few days out of town. The Old Sturbridge Village is a major stopping point with its living history knowledge and 17th-century artifacts; it is also one of the largest museum landmarks in the region! Wells State Park offers 12 miles of distinct hiking and horseback trails meant to take in the amazing woodlands and oak forestry. Westville Recreation Area is also around for any weekend visitor who likes downtown hikes and summer foliage near the Quinebaug River.

At Hyland Orchard, it is not hard to find friendly apple pickers, family barn tours with tractor riding, and fun animal petting. St. Anne Shrine Gift Shop is a great option for tourists who want to take home unique religious jewelry and statues. Seafood lovers may want to pay a visit to Sturbridge Seafood for the best meat dishes and lobster meals. For lodging, one can choose Publick House Historic Inn for modern charm and green beauty or Commonwealth Cottage for welcoming vibes and herb gardens.


A street in Northampton, Massachusetts. Editorial credit: EQRoy /
A street in Northampton, Massachusetts. Editorial credit: EQRoy /

Northampton, a cultural destination with 31,354 residents, is a top contender for weekend tourism and historical landmarks. The Smith College Museum of Art may appeal to anyone who loves artistic talent and historical Greek vases. Historic Northampton is another viable option for history lovers, with its 2.5-acre downtown estate containing rich 16th-century indigenous relics and lots of workshops related to the era of slavery. The Calvin Coolidge Presidential Library is a dedicated museum for former U.S. president Calvin Coolidge, with a large collection of political artifacts and writings related to his career!

Weekenders may grab a coffee at downtown Pulaski Park, a cozy and petite space where music and food vendors love showcasing their talents and cuisines. Norwottuck Rail Trail provides scenic rail walkways and shady areas to view happy cyclists and pet walkers. As for anyone needing a cocktail over the weekend, the Tunnel Bar delivers the finest drinks within an 1890s vintage train tunnel atmosphere! For anyone lodging in town, the Hotel Northampton remains a top choice for historical and cultural comfort. At the same time, the Sugar Maple Trailside Inn has more family-friendly amenities for laidback or leisurely enjoyment.


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

Sandwich is a small seaside town with 2,968 locals who cherish its history and beauty. The Heritage Museums & Gardens is the most prominent in town for weekend visitors who want a casual day filled with Cape Cod's history and artistic exhibits of the natural world. The Sandwich Glass Museum may also appeal to visitors with its Victorian sculptures and 18th-century glass-blowing demonstrations! For more history, tourists can even visit Hoxie House for a taste of 17th-century living and upbringing within one of the oldest estates across the Cape.

For a unique boardwalk experience, weekend travelers may like Sandwich Boardwalk, a frequented tourist zone for scenic marsh views, large dunes, and rocky beach photography. Hikers sticking around for a few days may enjoy Scorton Creek for pleasant wetland paddling and river exploration near East Sandwich Beach. Literature lovers may admire Titcomb's Bookshop for heartwarming books and toys for all ages, while hungry visitors can try award-winning croissants and Portuguese dishes at Cafe Chew. Those lodging in Sandwich for the weekend may want to check in at Sandwich Inn & Suites or Earl of Sandwich Motel for charming furniture and scenic canopy views.


Storefronts in historic Concord, Massachusetts. Image credit Joseph Sohm via Shutterstock
Storefronts in historic Concord, Massachusetts. Image credit Joseph Sohm via Shutterstock

A pretty town with 17,566 residents, Concord is known for its significant locales and landmarks. Weekenders may find that Louisa May Alcott's Orchard House is the best historic stop in town, with its famous farmhouse architecture and Alcott family household items dating back to the 18th century. History lovers can also visit Concord Museum for the weekend to learn about artifacts once belonging to famous authors Ralph Waldo Emerson and Hendry David Thoreau!

Sleepy Hollow Cemetery is another amazing weekend getaway idea for anyone who wants to witness a historic burial site related to famous settlers and authors from older periods. Hartwell Tavern creates a reminiscent era for visitors interested in American Revolutionary War history. Walden Pond offers clear waters and hiking trails near an open lakeside resort with plenty of interesting finds, like Thoreau's 18th-century cabin, and tranquility around Walden Woods. One can check in at Great Wolf Lodge for weekends full of family-friendly amenities and the best buffets and desserts!


Historic commercial buildings on Main Street in downtown Gloucester, Massachusetts
Historic commercial buildings on Main Street in downtown Gloucester. Image credit Wangkun Jia via Shutterstock.

A famous coastal town with 29,932 inhabitants, Gloucester is a wonderful weekend destination for travelers. The Hammond Castle Museum is full of breathtaking 19th-century architecture and pioneering history related to European influence and the New England shoreline. The Cape Ann Museum is another option for artistic collections and maritime history, with charming fishing exhibits and modern paintings that may appeal to anyone who loves marine ecosystems. For sunshine, one can visit Good Harbor Beach and Wingaersheek Beach, two of the best weekend vacation options for dog-friendly beachside activities and memorable oceanside beauty.

An interesting landmark worth checking out is the Gloucester Fishmern's Wives Memorial, a historic stop that honors the women of the town who represent the well-being of fishing communities. Weekenders who love pubs or bar-hopping may enjoy Stones Pub & Eatery, where welcoming locals and comfort soups are the best motivators for a return trip! For anyone lodging in town, the Ocean House Hotel at Bass Rocks is amazing for charming rooftop decks and hot tubs, while the Beauport Hotel offers cozy harbor views.


Beautiful seaside homes in Nantucket, Massachusetts.
Beautiful seaside homes in Nantucket, Massachusetts.

An isolated Cape Cod town with 10,039 residents, Nantucket is quite weekend-friendly and a guaranteed lighthouse paradise for tourists. The Brant Point Lighthouse is a major stop with its distinct sunsets and historic 17th-century island viewing pleasures. Great Point Lighthouse is a viable alternative for stone architecture and northernmost coastal lights that would stand out to anyone staying in town for a few days. For wildlife enthusiasts, Coskata-Coatue Wildlife Refuge creates a haven for weekend visitors and woodland species to interact with each other.

Madaket Beach is a great outdoor spot for laidback comfort, soft sands, and the most beautiful stopping point for sunsets if any weekender wants a quality evening! Loines Observatory is a unique research observatory with night sky telescope viewing events and astronomy history for anyone with a science-fiction itinerary. Nantucket Looms has downtown trinkets and artisanal goods for casual shoppers to satisfy easygoing locals and tourists. Aunt Leah's Fudge has the best chocolate treats and wrapped pretzel gifts around! For lodging, The Nantucket Hotel & Resort offers spacious rooms and complimentary cookies, while Cliff Lodge and Nantucket Inn have more laidback estate views and are easily convenient to town cores.


The Custom House at the Maritime National Historic Site in Salem, Massachusetts, USA.
The Custom House at the Maritime National Historic Site in Salem, Massachusetts, USA.

Salem, with a population of 44,970 residents, is a famous getaway destination worth exploring. The House of the Seven Gables is a colonial 16th-century mansion that has welcoming tours and American architectural history related to four centuries of architects and philanthropists. Weekenders can also visit the Witch House for fascinating witch-hunting trial history and the upbringing of colonial heritage from a once infamous era. For spooky pleasures and horror enthusiasm, weekend visitors may love Count Orlok's Nightmare Gallery, where overlooked fantasy creatures and life-sized creepy statues will scare anyone!

For a historical and cultural entertainment experience, visitors can walk through Gallows Hill, where live-action effects and ghostly projections make for a fun and thrilling trip. Nature lovers can enjoy Salem Common, a 17th-century park with calming stroll paths and clam chowder vendors! Winter Island Park also has great campsites and waterfront-oriented activities for weekend itineraries, with only a few days to take in the sun. Salem offers nice lodging amenities at the Hawthorne Hotel and The Merchant, known for its historic charm and boutique bars.

Great Barrington

Railroad Street lined with Traditional Brick Buildings and Colourful Shops and Restaurants. Great Barrington. Editorial credit: Albert Pego /
Railroad Street is lined with colorful shops and restaurants in Great Barrington. Image credit: Albert Pego via Shutterstock.

Seen as the central part of Southern Berkshire County, Great Barrington is home to 1,636 inhabitants and is worth any weekend itinerary. Windy Hill Farm is a natural getaway with its historical beauty and nursery stockings around pleasant apple orchards and blueberry fields. Hikers can also take in nature at Monument Mountain Reservation, a landmark full of steep loops and amazing clifftop perches to satisfy summit climbers. Those seeking more calming hikes can take on Housatonic Flats Reserve, where easy trekking routes and friendly bird-watching activities are always present.

AsiaBarong Gallery is one of the coolest locales to visit in town for anyone with a taste for South Asian or East Asian culture, offering traditional art styles and unique showing rooms that may surprise weekenders! Bernay Fine Art also has an art appreciation and admiration for downtown sculpturing and ceramics, including special welcoming events for tourists. Cyclists who need a new bike can check out Berkshire Bike and Board Great Barrington for new equipment; it also has fun weekend group-riding sessions! Resorts like The Barrington or Monument Mountain Motel may be worthwhile for artful decor and shopping and dining convenience.


Overlooking Marblehead, Massachusetts.
Overlooking Marblehead, Massachusetts.

Another coastal New England town with 20,256 locals, Marblehead is a North Shore destination worth any weekend out of town. The Jeremiah Lee Mansion has Georgian architecture and wealthy colonial relics belonging to the older colonial days. The Old Burial Hill Cemetery is another historical colonial site with some of the prettiest natural views beyond residential life that may astonish newcomers! Art lovers may revel in famous paintings and iconic brick architecture at Abbot Hall, a notable stop for Romanesque history and fascinating exhibits.

For a truly natural exposure, one can check out Crowninshield Island, an intimate coastal island with wooded hilltops and sandy beaches worth any return trip. Castle Rock Park is a nature stop for hikers who prefer rocky sightings and solitude around small beach areas. The Landing Restaurant is perfect for weekenders who crave blackened salmon and grilled swordfish. Crocker Park is a nice alternative for tourists who may want to see Marblehead Harbor up close with added emphasis on gazebo comfort. Those who book a few nights in town can stay at Harbor Light Inn or A Lady Winette Cottage for easygoing jacuzzi nights and hidden gems like backdoor cottage scenery.

These small towns in Massachusetts are the best for any weekend getaway plan. With all of the locales and landmarks around to please visitors from all wakes of life, there is so much to explore and remember for a lifetime over any given weekend. The "Bay State" is an easy destination to consider for tourists with its amazing natural views and historical significance, so anyone looking to book their next trip to the New England region may find this list handy!

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