11 Picturesque Towns in Massachusetts for a Weekend Retreat
Massachusetts might be one of the smallest states in the United States, but it sure knows how to make up for its size through scenic pint-sized towns! Megalopolises like Boston and Lowell win the numbers game, but the state’s tiny enclaves are where it truly shines and shows its beauty.
With the serene seaside burgs of Nantucket and Rockport, the historical center of Concord, the hiking trails of Westford, and Salem’s witchy past, there is a long list of things to do and see in this New England region. Practice your camera skills because you will be capturing lots of scenery from these small and picturesque towns in Massachusetts!
Rockport
Few coastal towns look as postcard-worthy as Rockport. In fact, not only is it a thriving fishing harbor, but it also became known as an artist colony for its beauty, attracting many painters, photographers, and art lovers over the years. So while you should make feasting on lobster rolls from Roy Moore Lobster Company a priority, do not skip out on witnessing the “most often-painted building in America”, the iconic and photogenic fishing shack Motif Number 1.
See more of what makes Rockport an art hub through its numerous galleries, like the Rockport Art Association and Museum, the Art Nook Gallery, or the art piece of The Paper House—a home made entirely of paper! Spots full of natural marvels are also aplenty, as shown by camping at Halibut Point State Park and lounging at Back Beach’s quarter-mile sandy shore. Cannot get enough of Rockport’s ocean-tastic charms? Reserve a room at the Bearskin Neck Motor Lodge to get premier waterfront views from its terrace.
Lenox
Hailing from the Berkshires in Western Massachusetts, Lenox is as beautiful as it is culturally and artistically rich—in more ways than one. What once were luxurious mansions during the Gilded Age are now history, music, art, and garden spaces for locals and tourists to enjoy. Besides the writing lectures and art exhibits at The Mount—writer Edith Wharton’s lavish abode, Shakespeare & Company and Tanglewood (Boston Symphony Orchestra’s summer home) will enrich your theater and orchestra-loving heart.
For a peek at the opulent lives of past Lenox residents, the Ventfort Hall Gilded Age Mansion & Museum offers a mansion tour and even a ghost-themed one for the not-so-easily rattled. If all these mansions made you want a taste of the deluxe lifestyle, book a night or two at The Playhouse, where icons like President McKinley and Nikola Tesla once stayed, or try the soon-to-reopen Blantyre. Then, reserve a table at Alta Restaurant for fine Mediterranean-inspired cuisine. Now that is a fancy, albeit educational, Massachusetts vacay!
Nantucket
A quick ferry ride off the coast of Cape Cod will take you to the adorable island escapade of Nantucket. Do not let its tiny size fool you, as it is jam-packed with stunning views and activities from its beaches, multiple lighthouses, museums, and festivals. No wonder National Geographic included it in their top 10 islands list!
Upon arrival, the jewel of Nantucket—Brant Point Lighthouse—will immediately welcome you, as are other harbor-centric spots like the Whaling Museum, the historic theater of Dreamland Film, and the galleries of East End, Pierce, and Pete's Fresh Fish Prints. Eager to dip your toes in the water? Try the gentle surf of Jetties Beach, or challenge yourself with the expert-level waves of Surfside. But if you would rather stay dry and just meander around, do a staycation at the luxe 4-star-hotel of White Elephant Nantucket or the quaint B&B of Brass Lantern Inn. There are plenty of boutique shops and eateries nearby to fill your time, like Lola 41’s seafood spread and Antiques Depot—one of the oldest antique emporiums on the island.
Concord
While Concord has no shortage of natural wonders, such as the inspiring Walden Pond that has struck the hearts of American authors Ralph Waldo Emerson and Henry David Thoreau, Concord’s true beauty lies in its historic legacy. As the site of the first battle during the Revolutionary War, history buffs should add the Minute Man National Historical Park to their itineraries. Its hiking trail will lead you to the North Bridge and its Minute Man statue overlooking the Concord River.
Continue your history crawl with a visit to the Concord Museum, the town’s cache of war artifacts, Thoreau’s works, and other bits and bobs related to American history. Other important historical sites in Concord include The Old Manse, author Emerson’s Georgian mansion; the 19th-century-era Robbins House; and the site of Captain David Brown’s house. To go with your history-themed vacation, stay at Concord’s Colonial Inn, a 300-year-old lodging with a colorful past—from being an arms storehouse during the Revolutionary War to housing Thoreau during his Harvard years.
Salem
Salem is best known for its witch hunts and trials back in 1692, and if your trip is focused on that, then you should not pass on visiting the Witch History Museum or doing the Bewitched Historical Tours. However, there is more to this coastal city than its spooky side, and you can get a good look at its bewitching natural panorama through sailing tours on vintage schooner yachts or hiking through Salem Woods (we promise it is not scary).
For downtown explorers, a Salem Trolley ride would do you good, as you will see the town’s cobblestone streets and eclectic shops (Harbor Sweets’ handmade chocolates and Emporium 32’s curiosities, anyone?). Staying in the heart of the town with The Merchant Hotel will let you be near all the action, but a weekend at Salem’s oldest inn—The Daniels House—might make for an immersive vacation.
Sandwich
There is something hauntingly beautiful about old things, which Sandwich has a wellspring of due to being the oldest town on the peninsula. Explore its well-preserved remnants from bygone times, like the Hoxie House Museum, a 1675 home considered to be the oldest saltbox house in the area. For a historical structure that truly encapsulates the meaning of picturesque, tour the lovely mid-17th century mill of Dexter Grist Mill. It still mills fresh bags of corn meal, which you can buy at its store.
Do not leave Sandwich without visiting the Heritage Museums and Gardens, where art, history, and nature merge in its exhibits. From vintage automobiles and pre-colonization huts to New England paintings and an old-timey carousel, you will need at least a full day to properly enjoy what this museum has to offer. After your trip down Sandwich’s memory lane, pamper yourself at the Dan’l Webster Inn and Spa. Your feet will definitely need a massage!
Oak Bluffs
Thought of as the most idyllic town in Martha’s Vineyard, Oak Bluffs will impress you with its row of adorable gingerbread cottage houses, a vintage carousel, and cinema-worthy beaches. The dollhouse-like abodes are not just eye candy—you can rent them via the Martha’s Vineyard Camp Meeting Association and even tour the Cottage Museum to learn about their 1800s origins.
As pretty as the houses are, Oak Bluffs’ beaches rival it in the scenic department. The nearby Joseph Sylvia State Beach is a two-mile stretch of sandy shores and sparkly water that got its time in the spotlight in the movie Jaws. Meanwhile, Oak Bluffs Town Beach, otherwise known as Inkwell Beach, is preferred by families and beginner swimmers for its calm waters. After a splash and a swim, relive your childhood at the country’s oldest platform merry-go-round—the Flying Horses Carousel. Other nearby places of interest are the galleries of Michael Blanchard and Alison Shaw, the antique store of Second Treasures MV, and the alpaca farm of Island Alpaca Company.
Provincetown
Located at the very tip of Cape Cod, this tiny shoreside town of around 3,000 people is one of the most popular summer hangouts in the region. Not only does it rake in as many as 60,000 tourists at the height of vacation season for its gorgeous beaches, but its progressiveness is also an attractive point for the LGBTQ+ community.
Provincetown is home to the oldest gay bar, the A-House, and has been the beating heart of the town’s nightlife for its dance club, jukebox sessions, and exciting Macho Bar. Stay in the Provincetown Historic District to be near the party and its history. The Pilgrim Monument and Provincetown Museum which honors the Mayflower pilgrims, Provincetown Town Hall’s live performance venue, Gabriel’s pet-friendly hotel, and the seafood eats of JD’s Woodfire Grill, are a stone’s throw away from each other. Beach-wise, Race Point Beach has unique activities other than swimming, such as whale watching and touring its old lighthouse.
Northampton
Go on a road trip to the artsy, funky, and free haven of Northampton. A hub for artists, academics, and activists, most of its attractions and activities come from Smith College, with Smith College Museum of Art and The Botanic Garden of Smith College as its top two tourist spectacles.
Downtown Northampton is a picture-perfect gem itself, with lots of excellent architecture and local businesses to admire. The bookstore nook of Thornes Marketplace, the Academy of Music’s grand concert hall, the 1927 Hotel Northampton, and the Historic Northampton Museum are just some of the must-see interesting places worthy of mention. Outside of town, spend some time with Mother Nature at Norwottuck Rail Trail to make your Northampton vacation more holistic.
Williamstown
Williamstown is undeniably one of the prettiest small towns in Massachusetts thanks to its 18th and 19th-century architecture, as seen by Williams College’s blend of Georgian Revival, Gothic Revival, and Collegiate Gothic styles. Some areas on the campus are open for visitors, such as the Williams College Museum of Art showcasing its American modernist collection, and the somber Gothic church of Thompson Memorial Chapel.
For a mix of man-made and Mother Nature-made art, stop by the Clark Art Institute and its 19th-century American and European paintings. The exhibit house is set in acres of lush forest, so you can go outside for a refreshing stroll after your gallery tour. Although it is a little ways off town, it is along a few Williamstown vacation spots, like the Tim Duncan Pottery (adult evening classes available), trek-worthy Fitch Trail in Fitch Memorial Woodlands, and the milking barn-turned-lodging of the 1896 House Inn.
Westford
Not many might know this, but Massachusetts actually hides a beautiful ski wonderland in one of its hills. Hit the slopes at the Nashoba Valley Ski Area, which has been in operation since 1964. Skiing, ski lessons, and tubing are the focus during winter, while off-season in the summer turns the place into the Tiki Trail 5K marathon venue. The Residence Inn and the Westford Regency Inn are great accommodation options for their modern amenities and proximity to the ski place, so you can get right back into ski action.
Outside winter, you can still enjoy Westford’s panoramic landscapes and sights through its year-round outdoorsy enticements. Love hiking? Tom Paul Trail, one of the longest trails in town, and the Stone Arch Trail, both end at the Stone Arch Bridge—an old 1872 bridge built along the nearby railroad. Into biking? The Bruce Freeman Rail Trail route that spans multiple Middlesex County towns might be a worthy challenge for you. Want to see the tiny flying charms of the outdoors indoors? The Butterfly Place has hundreds of butterflies in its indoor garden!
Final Thoughts
As seen from this list, Massachusetts is small but mighty. It might not have the landmass of its neighbors New York and Vermont, but it can pack a wallop when it comes to vacation destinations of the pretty kind!
More importantly, its beauty is not just superficial. Concord and Salem both show its historical relevance, Northampton has the allure of education, and Provincetown proves that an inclusive heart is a beaut in and of itself. Will you open your heart to these picturesque towns in Massachusetts on your next travel?
