The Best Small Towns in Massachusetts to Chill Out In 2024
Massachusetts, one of the country's smallest states, is also one of the most accessible, diverse, and fun to explore and chill out in. Salem's larger size matches the attractions and deep history around the infamous witch hunts and trials of the 17th century, set against beautiful architecture and waterfront views. Edgartown is a naturally rich, uncrowded Martha's Vineyard destination, with its own island, a lighthouse, and a beautiful Japanese garden.
Settled by the Mayflower Pilgrims in 1620, Massachusetts has grown to be a popular destination in all four seasons, from renowned foliage to skiing and sunbathing. Rockport, a tiny fishing village, is home to Motif No. 1, a must-see attraction when in New England. The Berkshire Mountains in Western Massachusetts are a picturesque place to relax without crowds, ski, and join the fun during the renowned Tanglewood Music Festival in Lenox.
Edgartown
Tucked on the easternmost part of Martha’s Vineyard just off the Cape Cod coast, Edgartown is one of the largest by area yet smallest in population among the scenic isle's five towns. With a waterscape on three sides and only 600 locals to its name, the sunny town encompasses a dozen attractions, such as the historical Edgartown Lighthouse and the serene Mytoi Japanese Garden, with trails, ponds, traditional Japanese sculptures, and seasonal blooms. South Beach State Park/Katama Beach lures surfers with strong waves and beautiful sunsets from this three-mile barrier beach. To the north, Jaws Bridge is great to relax along its scenic overpass for cars and pedestrians, with diving allowed next to the serene Edgartown Beach.
Often called Martha's most picturesque town, Edgartown inspires a blissful island lifestyle through a charming downtown area and a reputable food scene. Visitors can enjoy local shopping and admire authentic New England homes along historic brick streets with white picket fences and beautiful gardens. In addition, Edgartown's very own Chappaquiddick Island, as large as itself, is a dream for hikers and nature lovers, with coastal trails, grasslands, and marshes through Wasque Point Wildlife Management Area, hooking around Cape Poge Bay. Relax among sandpipers, herons, and butterflies on a hike northward along this truly unspoiled slice of the state, past the Dike Bridge, to the Cape Poge Lighthouse at the tip.
Gloucester
While not as famous as its UK namesake, Gloucester is a historic, vibrant, and uncrowded center for sailing and seafood along the stunning North Shore coastline. Once a major center for the granite industry, its thriving fishing port past is very much alive along the Maritime Gloucester, a waterfront neighborhood, while Cape Ann Museum displays regional history. Offering many scenic places to relax, such as the cozy Good Harbor Beach, with prime swimming conditions, dunes, and marshes to explore, Coffins Beach is a little local secret to the north, with 360° views and vast sandbars amid cerulean waters.
Take a sailboat into the Atlantic, relax on a cruise, or stay dry along the easily scenic Gloucester Harbor Walk. When you come to relax this August at the fun Gloucester Waterfront Festival, the Hotel at Cape Ann Marina offers a family-friendly feel and waterfront views. Built by inventor John Hays Hammond Jr. as his home, laboratory, and museum, the Hammond Castle Museum is a great place to enjoy a photoshoot and a tour with exhibits and life essentials still on display. Don't miss the Fisherman Memorial and painter Winslow Homer's one-time home, the 1890 Eastern Point Lighthouse, with an operating tower, and now you're set to dine at Lobstah Land, a seasonal mainstay.
Lenox
Lenox, a hidden Berkshire Mountains gem in western Massachusetts, is a picturesque town to chill out in every season, including wintertime skiing. Exuding old New England charm, its rich cultural heritage is alive along the historic streets of Lenox Village with stunning architecture, gardens, and parks. Chill among the best musicians and performers from around the world during the infamous Tanglewood Music Festival. This electrifying live music concert takes place in the verdant outdoors, against "peak" scenery. Lenox's several reputable inns and popular restaurants promise an atmosphere for every taste, from comfort to mountain authenticity.
In the summer, chill out with resident beavers through Mass Audubon's Pleasant Valley Wildlife Sanctuary via easy trails and rugged hikes through forests, meadows, and marshes. Attracting artists, musicians, and writers behind all the boutiques and galleries, discover Lenox's artsy side at Shakespeare & Company, a performance venue. The 1893 Ventfort Hall Gilded Age Mansion & Museum, built in Jacobean revival style, is open for tours, while Haven serves an upscale American breakfast and lunch menu in the heart of downtown, with outdoor seating and an on-site bakery scent mixing into the inebriating fresh mountain air.
Manchester-by-the-Sea
Manchester-by-the-Sea, a historically quaint Essex County town, embodies the Old Man and the Sea tale along the coast. Starting with a scenic drive offering stunning ocean views, it provides a relaxing seaside escape for beach lovers, architecture enthusiasts, and sightseers. Home to authentic New England architecture, wandering along the narrow, brick-faced streets with historic landmarks in the sea breeze feels like flipping through the pages of a history book. Enjoy nature at Masconomo Park with its gazebo, relax in the scenic serenity of Lobster Cove Beach, where you can spot the elegant Manchester-by-the-Sea Lighthouse to the west, or make the dry sands sing by shuffling your feet along the Singing Beach.
The charming downtown area offers local shopping and dining for every taste, along with regular events in an artistically and culturally diverse community, like the unique Manchester Music Festival. From solo piano recitals to full orchestral performances, the classical music festival attracts talented musicians from around the world to beautiful venues like Tucks Point and the stunning Manchester-Essex High School auditorium. This all-inclusive festival is enjoyable for all, with workshops and masterclasses for aspiring musicians, making it feel personalized. The popular Manchester-by-the-Sea Film Festival screens everything from heartwarming dramas to thought-provoking documentaries.
Marblehead
Marblehead is not just another North Shore town but an evocative seaside destination with a fairytale vibe along its narrow, winding lanes with historic architecture. Authentic and photogenic from all sides, many come to relax under the sun along the soft sands, splash in the crystal-clear sea, and enjoy beachcombing against stunning ocean vistas. Devereux Beach/Ocean Ave. offers sandy walkways and access to the neighboring Marblehead Neck Wildlife Sanctuary with refreshing trails and wildflowers. Just to the east, the lush Castle Rock Park boasts beautiful ocean views and hiking trails to explore in the pleasant sea breeze, spurring you on until a picnic area or playground tempts a member of your group.
Before sunset, head northwards towards Chandler Hovey Park with grassy areas, picnic tables, and benches to watch the Atlantic put out the last fiery rays at dusk. Home to several museums and historic sites downtown, like Abbot Hall and the town's arts association, don't miss the stately Jeremiah Lee Mansion or the Old Burial Hill Cemetery. Marblehead Museum offers specific town history, while the early 1700s Fort Sewall, built to defend against sea attacks, is free to enter and provides a stunning backdrop against the harbor, with hardly a soul in sight. Looking out into the ocean beyond, the timeless feel encompasses you on a relaxing stroll in the fresh air as sails go by, until it is time for a seafood feast at Barnacle.
Rockport
Rockport, the easternmost town in the Bay State, in a tight embrace with Sandy Bay, invites one and all to relax by the infamous Motif No. 1, with 360-degree views of the coastline. The iconic red fishing shack exudes a unique charm through town, maximizing Rockport's authentic fishing village feel. Painted by many artists over the years, it is "the most painted building in the US." Surrounded by beaches with different vibes and stunning marine vistas, visitors can enjoy swimming and sunbathing, as well as boat tours and kayaking adventures available through rental companies or local tour agencies. For a cool stay, the top-rated Seafarer Inn offers top views of the Straitsmouth Island Light Station on the eponymous island.
Rockport's local culture, scenery, and relaxing atmosphere extend onto the beachfront of Halibut Point State Park, a 440-million-year-old granite formation with spectacular views, wildflowers, and a visitor center. Tiny yet bursting with activities, Bearskin Neck, a street through the heart of town, is a landmark in its own right. Visitors can stroll along a colorful lineup of independent shops, browse galleries, and find handmade art, crafts, artisanal gifts, and unique miscellanea. Stop at the end of the street to relax along the breakwater against the "Captain Hedge Ocean View." You might spot a seal or two swimming in the harbor or simply enjoy the harborfront views from another perspective before dinner at the illustrious neighborhood, which offers a choice of seafood restaurants.
Salem
Home to under 45,000 residents, this larger small town, known worldwide for the infamous witch trials of the late 1600s, attracts paranormal hunters eager to see if the spirits of the hanged "witches" still linger. Quaint and historic, with beautiful architecture and waterfront views, Salem can be a literally "chilling," evocative, or nature-centric escape. Whether you take one of the hundreds of themed tours or a self-guided walk, the legends of both true and exaggerated origins are fun to discover for those interested in a dark history lesson. Notable landmarks include the Witch Trials Memorial and the Salem Witch Museum for an in-depth look into the 1692 trials and deaths of twenty innocent people. The Witch Dungeon Museum offers live reenactment shows of the 1692 Salem witch trials and tours through a dungeon replica.
Beyond the witch-related attractions, Salem is a charming New England getaway, home to Derby Wharf Light Station, art, and seafood. From intricate Chinese art to stunning ship models, the Peabody Essex Museum flaunts an impressive collection of worldwide art and artifacts, as well as New England's maritime history, displayed throughout beautifully curated galleries, providing a unique and accessible glimpse into the fascinating past. Salem Pioneer Village is a recreated 17th-century colonial village along the waterfront, while the restored 1668 House of the Seven Gables, which inspired Hawthorne's novel, offers tours and verdant seaside gardens. Wilderness is right at the doorstep along the tranquil nature trails through Salem Woods Highland Park and woodlands, connecting to marshland with 1.5 miles of hiking trails at the neighboring conservation area.
Home to around seven million people over some 10,565 square miles with a vast coastline, the Bay State is a prime destination for beachcombing, like Devereux Beach/Ocean Ave., a sandy walkway to Marblehead Neck Wildlife Sanctuary for trails and wildflowers. Manchester-by-the-Sea features a serene cove-like beach, an elegant lighthouse, and the Singing Beach, where you can make the sands sing by shuffling your feet.
From artsy enclaves to preppy seaside villages and charming mountain towns, lace up those hiking shoes and conquer the peaks and scenic trails around Lenox. Boston is considered the heart of New England, so whether you're exploring the mountains or the seacoast on a quick getaway from the capital or out of state, you're at the cultural heart of New England's charm and history.
