Aerial view of Newburyport, Massachusetts.

10 Serene Towns In Massachusetts For A Weekend Retreat

The Commonwealth of Massachusetts, one of the six states in the American Northeast’s New England region, is renowned for its natural splendor as well as its rich history and culture that predates and aptly encapsulates the experiences of the nation as a whole. Travelers who wish to vacay in this picturesque state bounded by the mighty Atlantic in the east and southeast mostly prefer to tour the crowded urban centers like Cambridge, Springfield, Worcester, and the state capital, Boston, rather than the innumerable serene communities scattered all over the state. Nevertheless, these tiny towns are worth exploring and are excellent locales for a rejuvenating weekend in the Bay State.


Aerial view of the Main Street in the town of Concord, Massachusetts
Aerial view of the Main Street in the town of Concord, Massachusetts.

An enchanting Middlesex County town, Concord is located in Eastern Massachusetts, close to where the Assabet and Sudbury rivers confluence to form the Concord River, approx. 20 miles northwest of Boston. Currently a prosperous Boston suburb and notable tourist destination, the town’s peaceful surroundings and interesting landmarks aptly reflect its significance as the location of the Battles of Lexington and Concord that ultimately led to the start of the American Revolutionary War. The Minute Man National Historical Park, Old North Bridge, Louisa May Alcott’s Orchard House, Wheeler-Minot Farmhouse, Old Manse, Sleepy Hollow Cemetery, Concord Museum, and the Walden Pond State Reservation appeal to both heritage and literature buffs. Outdoor enthusiasts must survey the several miles of wooded hiking trails in the Great Meadows National Wildlife Refuge, peruse the different specialty shops and eateries in the walkable downtown, and rest for the night at either Concord’s Colonial Inn or North Bridge Inn.


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

Newburyport is a charming coastal community in Essex County in the state's northeastern corner, roughly 35 miles northeast of Boston, near the Merrimack River’s mouth. Initially settled in 1635 as part of Newbury, the town draws vacationers with spellbinding views of the Atlantic and a plethora of recreations all year round. Newburyport’s downtown shopping district, with uncountable locally-owned businesses and restaurants around Market Square, caters to visitors of every taste. Many Federal-style properties stand as a stark reminder of the settlement’s nautical heritage, aside from other tourist attractions such as the Cushing House Museum & Garden, Newburyport Chain Bridge, Maudslay State Park, Custom House Maritime Museum, Old South Presbyterian Church, and the adjoining Parker River National Wildlife Refuge. Enjoy your stay at the Essex Street Inn & Suites and find time to attend any of the town’s annual events like Yankee Homecoming, Newburyport Chamber Music Festival, Newburyport Literary Festival, and Waterfront Concert Series.


The beautiful seaside town of Provincetown, Massachusetts
The beautiful seaside town of Provincetown, Massachusetts.

Often called “P-town,” this teeny seaside resort is located on Cape Cod’s outermost edge in Eastern Massachusetts’s Barnstable County. Abutted by the Cape Cod National Seashore, Provincetown captivates holidayers with its impressive soft sand beaches, trendy tourist atmosphere, engaging maritime history, and exhilarating nightlife. Additionally, the town has earned the distinction of being America’s oldest continuous art colony, where for eons, artists from all over the globe have been flocking to the Cape Cod School of Art founded by Charles Hawthorne. The lively Commercial Street is chock-a-full of antique stores, cool boutiques, souvenir shops, museums, unrivaled restaurants, and hotels like the Pilgrim House, the Harbor Hotel, and the Red Inn. Also, do not forget to tour the Pilgrim Monument - Provincetown’s most prominent landmark, and partake in the town’s yearly celebrations such as First Light Provincetown, Provincetown Jazz Festival, Provincetown PRIDE, Provincetown Portuguese Festival, and Provincetown International Film Festival.


Lenox, Massachusetts
The Mount, the country home of the writer Edith Wharton, in Lenox, Massachusetts. Editorial credit: Heidi Besen /

Lenox, a popular summer tourist retreat, forms a part of the Pittsfield Metropolitan Statistical Area amidst the Berkshire Mountains in Western Massachusetts’s Berkshire County. Initially called ‘Yokuntown’ and inhabited by native Mahicans, the area was first settled by Jonathan and Sarah Hinsdale from Hartford, Connecticut. When visiting the town, do stop by the Berkshire Scenic Railway Museum, The Mount - residence of the eminent American author Edith Wharton, the Pleasant Valley Wildlife Sanctuary, the National Register-listed Ventfort Hall Mansion & Gilded Age Mansion, Church on the Hill, Shakespeare & Company, Tanglewood Music Center- the Boston Symphony Orchestra’s summer home, and the Kennedy Park - perfect for picnics, hiking, and cross-country skiing. For a premier dining experience, visit the Alta Restaurant & Wine Bar, where you can taste Mediterranean cuisine mixed with wines. Unwind after a hectic day at the modern luxurious rooms of the Birchwood Inn Bed & Breakfast.


A country estate near Stockbridge, Massachusetts.
A country estate near Stockbridge, Massachusetts. Editorial credit: Bob Pool /

Dubbed after its namesake English town, this Berkshire County town is located along the Housatonic River in the Berkshire Mountains, approximately 12 miles south of Pittsfield. Primarily settled in 1734 by British missionaries as a praying town for the indigenous Stockbridge Indians, this picture-perfect town is a famed ‘art colony’ and hometown of the well-known sculptor Daniel Chester French and distinguished American painter Norman Perceval Rockwell. Stroll down Stockbridge’s vibrant Main Street and take note of the myriad Gilded Age structures, art galleries, specialty shops, boutiques, diners, and cozy hotels like The Red Lion Inn and Stockbridge Country Inn. The Norman Rockwell Museum, Lake Mahkeenac (Stockbridge Bowl), Berkshire Botanical Garden, National Shrine of The Divine Mercy, Naumkeag Mansion & Gardens, Chesterwood - residence & studio of Daniel Chester Wood, Merwin House, Mission House, and Lenox Station Museum are Stockbridge’s noteworthy attractions. Revelers can traverse the three recreational trails, the Mary V. Flynn Trail, Ice Glen Trail, and Laura’s Tower Trail, or watch a performance by the Berkshire Theatre Group.


Coast Guard Station at Chatham, Cape Cod
Aerial view of the lighthouse and Coast Guard Station at Chatham, Cape Cod.

Occupying the “elbow” of Cape Cod in Barnstable County, Chatham, bounded by the Nantucket Sound to the south and Atlantic Ocean to the east, is situated about 85 miles southeast of Boston and 35 miles south of Provincetown. A fishing, whaling, and shipping hub at the beginning, Chatham developed gradually over the years into a favored summer resort destination mesmerizing tourists with its immaculate beaches, white steeple churches, tidal shoals, fleeting sandbars, miles of saline channels, coves, and barrier islands. The town’s spirited Main Street is full of fashionable boutiques, art galleries, bookstores, gift shops, award-winning restaurants, and accommodations like Chatham Wayside Inn. The Commercial Fishing Pier, Chatham Orpheum Theater, Atwood House Museum, Chatham Lighthouse, Shark Center, Monomoy Natural Wildlife Refuge, Chatham Railroad Museum, Chatham Marconi Maritime Center, and Stage Harbor Light are some must-visit points of interest.


Harbor at Rockport, Massachusetts
Harbor at Rockport, Massachusetts.

Rockport is a small seaside community situated at approximately Cape Ann Peninsula’s northernmost extremity in Essex County, approximately 40 miles east of Boston and 20 miles east-northeast of Salem. Boasting undisturbed walking trails through coastal forests, miles of soft sand beaches, quaint fishing shacks, and ancient lighthouses, Rockport is an ideal locale to unwind. A state-designated Cultural District, the town’s Main Street is jam-packed with clothing boutiques, candy stores, gift shops, art galleries, eateries, and hotels like Sally Webster Inn Bed & Breakfast and Addison Choate. Vacationers must not miss the town’s leading attractions, including the Halibut Point State Park & Halibut Point Reservation, Front Beach, Bearskin Neck, Rockport Art Association & Museum, Motif No. 1 building, Shalin Liu Performance Center, Paper House Museum, and the neighboring Thacher Island.


The quaint town of Sandwich, Massachusetts
The quaint town of Sandwich, Massachusetts.

Sandwich, called after its same-named seaport in southeast England, is Cape Cod’s oldest settlement situated in Barnstable County immediately east of Bourne along Cape Cod Bay. Inhabited by the native Wampanoag tribe before colonization by a team of settlers from Saugus, this historic community is well-liked for its carefully maintained colonial structures and six spotless beaches. The Heritage Museum & Gardens, Hoxie House, Dexter Grist Mill, Sandwich Friends (Quaker) Meetinghouse, Sandwich Glass Museum, Wing Fort House, Green Briar Nature Center & Jam Kitchen, and Cape Cod Canal Visitor Center are some interesting sites. Furthermore, outdoor lovers must discover the Shawme-Crowell State Forest and Scusset Beach State Reserve, head to the Sandwich boardwalk for summer seaside fun, and enjoy their stay at comfortable accommodations like Sandwich Inn & Suites and Earl of Sandwich Motel.

Oak Bluffs

Gingerbread cottages in Oak Bluffs, Massachusetts
Gingerbread cottages in Oak Bluffs, Massachusetts.

A prime mecca of African-American culture since the 18th century, this blissful town located on Martha’s Vineyard Island in the state’s Dukes County is lauded for its remarkable ‘gingerbread cottages’ and other painstakingly maintained mid-to-late 19th century properties. Being one of the main arrival points for summer holidayers, beachgoers visiting Oak Bluffs can access the four public beaches: Joseph Sylvia State Beach, Oak Bluffs Town Beach (The Inkwell), Eastville Beach, and Hart Haven Beach, while the Oak Bluffs’ harbor lure recreational boaters throughout the year. Browse the scores of small businesses lining Oak Bluffs’ Main Street, tour East Chop Lighthouse, spend time outdoors at Ocean Park, watch a movie at Strand Theatre, take a fun ride on the Flying Horses Carousel, play a round of golf at Farm Neck Golf Cub, and relax at Pequot Hotel and The Dockside Inn.


Thompson Memorial Chapel in Williamstown, Massachusetts
Aerial view of the Thompson Memorial Chapel in Williamstown, Massachusetts.

Massachusetts’s northwesternmost town, this college town in Berkshire County, shares a boundary with New York in the west and Vermont in the north. Apart from being home to the principal campus of Williams College, Williamstown is a classic retreat for cultural enthusiasts. When in town, inspect the extensive art collections housed in the Sterling & Francine Clark Art Institute and the Williams College Museum of Art. Also, stop by the 316-acre Field Farm and the 1753 House, besides checking out the permanent exhibits displayed at the Williamstown Historical Museum, providing exclusive insights into the town’s past. Savor mouthwatering locally sourced American cuisines and craft cocktails at the Mezze Bistro & Bar, and de-stress after an eventful day at The Williams Inn.

From the charming alpine town of Stockbridge to the Cape Cod towns of Provincetown and Chatham, the small towns in the nation’s 6th smallest and 16th most populous state enthrall holidayers with their distinctive allure. Having extraordinary scenic beauty, historical attractions, colorful celebrations, multiple recreations, and restaurants serving lip-smacking cuisines, these pretty towns in the Pilgrim State are perfect to soothe one’s soul away from the dizzying distractions of busy city life.

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