Newburyport, MA, US. Editorial credit: Heidi Besen / Shutterstock.com

12 Serene Massachusetts Towns For A Weekend Retreat

The United States is known for a plethora of tranquil, serene towns, like Cannon Beach, Oregon, and Bar Harbor, Maine. Yet the state of Massachusetts has its own share of peaceful, charming towns. From the town of Great Barrington and the Housatonic River Walk to Rockport and Halibut Pointe State Park, there are a vast score of places in Massachusetts that provide the beauty and charm of nature. From Williamstown in Berkshire County to the town of Ipswich in Essex County, here are a dozen of the most serene, peaceful towns in Massachusetts that are ideal for a weekend retreat with family or friends.

Great Barrington

Great Barrington is Both a summer resort and home to Ski Butternut
Great Barrington is Both a summer resort and home to Ski Butternut. Editorial credit: Albert Pego / Shutterstock.com

Great Barrington, situated in southwestern Massachusetts, has several awesome natural attractions. Monument Mountain, with its 500-meter-high Peeskawso Peak, provides serene, panoramic vistas of the Housatonic River Valley. Housatonic River Walk, located in town, offers tranquil strolls along the Housatonic River. There are even guides available (on paper) for both the upper and lower sections of this fabulous walk.

Another serene natural attraction in Great Barrington is Fountain Pond State Park. This state park provides the option to walk around Fountain Pond, picnic with the family, or even hike through the forest along one of the various hiking trails. If you are staying in town for the weekend, Great Barrington is home to Wainwright Inn, which offers all the amenities expected in an excellent bed & breakfast inn.

Wellfleet

Uncle Tim's Bridge in Wellfleet, Massachusetts
Uncle Tim's Bridge in Wellfleet, Massachusetts

At the opposite end of the state, the quaint town of Wellfleet is an outdoor enthusiast’s dream come true. From Marconi Beach, which is a part of the Cape Cod National Seashore to the Mass Audubon Wildlife Sanctuary, situated off Wellfleet Bay, charming views of the rugged Atlantic Ocean can be enjoyed in the town of Wellfleet.

This New England coastal town is home to another natural attraction that provides serenity to those who experience it. Uncle Tim’s Bridge, which leads across Duck Creek to Hamblen Park, is only a short distance from downtown, yet it presents its own taste of tranquility. Relatively close to Hamblen Park, the Copper Swan B&B offers comfy, cozy rooms, great service, and a tasty breakfast the next morning.

Ipswich

Historic commercial buildings on Main Street in the historic town center of Ipswich, Massachusetts, USA
Historic commercial buildings on Main Street in the historic town center of Ipswich, Massachusetts, USA. Editorial credit: Wangkun Jia / Shutterstock.com

From Sandy Point Reservation on Plum Island to Crane Wildlife Refuge, the town of Ipswich has a plethora of serene locations, allowing for a calm atmosphere. Sandy Point has 77 acres of hiking landscape, with an awesome coastal beach that is ideal for catching some waves. Crane Wildlife Refuge, located on Crane Estate, features more than 200 species of migratory birds.

The town of Ipswich has many other great natural amenities that rate it as one of the ideal spots perfect for that weekend retreat. One of the best, Wolf Hollow, allows for guests to interact safely with the grey wolf. Plus, if you are planning on staying for an entire weekend, Kaede Bed & Breakfast offers an intimate, romantic setting, for those who might be thinking of planning a 1st, or even 2nd, honeymoon.

Concord

Concord, Massachusetts
Concord, Massachusetts. Image: Wangkun Jia / Shutterstock.

The town of Concord, home to Louisa May Alcott’s Orchard House and Minute Man National Historical Park, has a serenity that cannot be felt without experiencing it firsthand. The Orchard House, which was built in the 1600s, became the home and setting for “Little Women,” best-selling novel by Louisa May Alcott, in the 1800s. The Minute Man Park is the site of the first battle of the American Revolutionary War in 1775.

Some other serene attractions in the town of Concord include Walden Pond State Reservation and the Wayside Inn. Walden Pond Reservation provides opportunities for some great snapshots of the charming and quaint Walden Pond, known through Henry David Thoreau, acclaimed writer who lived there from 1845 to 1847. The Wayside Inn, while known for its hundred-plus acres of beautiful landscape and award-winning meals, is also known as America’s oldest continually-run inn.

Lenox

The Mount - the home of the American author Edith Wharton in Lenox, Massachusetts
The Mount - the home of the American author Edith Wharton in Lenox, Massachusetts. Editorial credit: LEE SNIDER PHOTO IMAGES / Shutterstock.com

Home of the Pleasant Valley Wildlife Sanctuary, which is over a thousand acres of wilderness, has several picturesque hiking trails, including Pike’s Pond Trail and the Overbrook Loop, the town of Lenox is perhaps one of the most scenic, serene places in the state. Kennedy Park also calls Lenox home. With it being only a short hike from downtown Lenox, most visitors choose to stop by every time they are in town.

There are also several art galleries in the town of Lenox, in case you consider art as an incorporeal way to experience the serene and the calming, The Wit Gallery and An American Craftsman Gallery are both close by to add that sense of warmth and cozy eloquence. If you plan on staying overnight, Gateways Inn is one of the best B&Bs in Lenox.

Brewster

The iconic Brewster Store. Brewster, Massachusetts.
The iconic Brewster Store. Brewster, Massachusetts. Image credit Arthur Villator via Shutterstock

Another coastal town on Cape Cod, the quaint town of Brewster is home to the Nickerson State Park and Paine’s Creek Beach, making this small town an outdoor enthusiast’s dream come true. Paine’s Creek Beach is best known as one of the most iconic beaches to view the sunset on the Atlantic Ocean. Nickerson State Park, 2,000 acres of beauty and tranquility, is also a full-service campground.

Brewster is also home to Crosby Mansion, known as Tawasentha when it was first constructed in 1888, and Stony Brook Grist Mill, which is a serene step back into the past of the 17th century through its existence within Factory Village. And, if you are planning on taking the family for the entire weekend, there are several awesome inns in and around town, including the Candleberry Inn Bed & Breakfast.

Rockport

The adorable downtown area of Rockport, Massachusetts.
The adorable downtown area of Rockport, Massachusetts.

Home of Halibut Pointe State Park, which features a scenic hike along the Halibut Pointe Trail, as well as opportunities for fishing, bird-watching, and picnicking with family or friends, the picturesque town of Rockport has tranquility covered. There are even several great lodging choices in Rockport, for those who wish to stay the weekend. Captain’s Bounty on the Beach offers comfy rooms and great service.

Some other awesome attractions around Rockport include Twin Lights on Thatcher Island, with the options for whale watching, and Front Beach, which is located quite close to downtown and promises some phenomenal sights of the Atlantic. Plus, the town of Rockport is famous for the Paper House, which was built in 1922 with approximately 100,000 varnished newspapers.

Oak Bluffs

The tourist information center in Oak Bluffs, Massachusetts
The tourist information center in Oak Bluffs, Massachusetts. Image credit Rolf_52 via Shutterstock

A part of Martha’s Vineyard, the town of Oak Bluffs has just over 5,000 residents. Yet this picturesque town has more than its share of serene, charming attractions, including Ocean Park and Joseph Silvia State Beach. While Joseph Silvia promises two miles of sparkling sands, with panoramic views of the Atlantic Ocean, Ocean Park is a 7-acre piece of land, providing everything from vistas of the sea, several iconic Victorian homes, and a grassy space perfect for picnicking.

Some other great attractions in Oak Bluffs, both the Cottage Museum on Trinity Park and the more than three hundred Gingerbread Cottages at the Oak Bluffs Campground are well worth the walk. Plus, if camping is what you are looking for, Oak Bluffs offers camping at the Martha’s Vineyard Campground, only three miles away from downtown.

Williamstown

Spring St. in Williamstown, Massachusetts
Spring St. in Williamstown, Massachusetts. Editorial credit: Adam Gladstone / Shutterstock.com.

On the opposite end of the state, Williamstown is best known for being home to the Taconic Trail State Park, which has several phenomenal hiking trails, like the Petersburg Pass Loop, Birch Hill Loop, and the Mills Hollow Trail Loop. Taconic Trail is also famous for its serene picnicking area, its fishing, and its close proximity to a plethora of great places to stay overnight. And, the 1896 House Inn is located between Williamstown and the park.

Williamstown is also home to several great art museums and theaters, for those who prefer serenity in art. The Clark Art Institute has some of the most serene grounds and a reflective pool that is amazing. The Williams College Museum of Art features outdoor sculptures. There is also Hopkin’s Memorial Forest just outside of Williamstown. It has a four mile loop that is breathtaking.

Provincetown

Commercial Street in Provincetown, Massachusetts
Commercial Street in Provincetown, Massachusetts. Editorial credit: Mystic Stock Photography / Shutterstock.com

Another awesome town along the inside tip of Cape Cod, the town of Provincetown has a plethora of phenomenal beaches from Race Point to Herring Cove. Each of these great beaches offer suntanning, swimming, fishing, boating, kayaking, and/or bird-watching. Plus, in town, Provincetown is famous for Commercial Street, which supplies its own form of serenity in the quaint shops and eateries, like Tin Pan Alley.

Home to Provincetown Causeway and Macmillan Pier as well, this quaint coastal town of around 3,000 people is home to several great amenities. Plus, if there is too much in this town to enjoy in one day, there are several bed & breakfast inns within town. The Sandcastle Resort & Club offers a wide selection of studios and suites that are comfortable, and it is conveniently located on Commercial Street.

Deerfield

Historic Deerfield Museum Gift Shop and Bookstore in Deerfield, Massachusetts
Historic Deerfield Museum Gift Shop and Bookstore in Deerfield, Massachusetts. Image credit Alizada Studios via Shutterstock.com

The small town of Deerfield, approximately 16 miles north of the city of Amherst, is home to several tranquil yet historic attributes. The New England Museum of History & Culture, otherwise known as Historic Deerfield, has exhibits featuring over a century of history between the 1730s and the 1840s. And the Old Deerfield Country Store, another great walk back into the annals of time, is reminiscent of what general stores used to be like.

A couple of other great choices in comfort and tranquility, the town of Deerfield is home to several awesome restaurants and bed & breakfast inns, for those who prefer to take more than a day exploring the area. The Deerfield Inn, first opened in 1884, provides comfortable rooms, while Champney’s Restaurant, a part of the inn, offers a beautiful ambiance as well as tasty cuisine.

Newburyport

Downtown street in Newburyport, Massachusetts
Downtown street in Newburyport, Massachusetts. Image credit Heidi Besen via Shutterstock

Along the coast of the Atlantic, with the Merrimack River flowing through town, the town of Newburyport is home to several tranquil attractions that will provide a sense of peace, as well as the fun of being away from home. Parker River National Wildlife Refuge features Plum Island Lighthouse and the Hellcat Dike Observation Tower, among others, while Maudslay State Park offers 19th century gardens that will leave you breathless.

Downtown Newburyport is also filled with a plethora of attributes that provide tranquility and serenity. Waterfront Park, located on the edge of downtown, allows for visitors and guests of the town of Newburyport to enjoy watching the boats enter and leave the harbor. Plus, in close proximity to the park, Compass Rose Inn offers great rooms and an even better breakfast the next morning.

From the town of Great Barrington in Berkshire County and Monument Mountain to the town of Newburyport in Essex County and the Merrimack River, the great state of Massachusetts is loaded with a plethora of awesome towns with great attractions. Whether you are visiting Massachusetts for the tranquil, peaceful parks and natural wonders, or whether you prefer a fine-dining restaurant and a picturesque inn providing elegant food and ambiance. Massachusetts is the place for you.

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