7 Towns In Massachusetts That Were Ranked Among US Favorites
Massachusetts, one of the country's smallest states, is the second-most popular in New England after Maine. It is home to small towns as varied as they come. For example, Norman Rockwell lived in Stockbridge, while Rockport flaunts the iconic Motif 1—America's most painted house. Again, Great Barrington is an "old soul" in the mountains, with Revolutionary War sites drowned by stunning landscapes and nature preserves.
As a visitor, you can look forward to spending a memorable time in these towns. Dine like President Washington did in Lexington or follow the painter's footsteps in a town straight from a painting. Melrose blends the lifestyle attractions that contest a busy city with a serene natural landscape of wide open spaces to explore. From artsy enclaves to preppy seaside villages, the first town flaunts unsurpassed natural beauty, the famous Chatham fogs, and great shopping. So, topple down on a pair of skis, hike the scenic trails, or lounge on the beaches to see why these towns are America's all-time favorites.
Chatham
Incorporated in 1712, Chatham shines with old-fashioned charm and a no-joke shopping scene. Nestled amid wild barrier islands, tidal shoals, and fleeting sandbars, the high ground affords unsurpassed natural beauty, including the infamous Chatham fogs. The historic 1887 train depot, the Chatham Railroad Museum, features model locomotives from the 1939 New York World’s Fair and a restored 1910 caboose. Stop by the Chatham Marconi Maritime Center to celebrate the first wireless transmission between the US and Norway. Flaunting it all on the southern terminus of Cape Cod, plus picture-perfect beaches for lounging, photography, and endless boating opportunities, visitors can enjoy bike paths and nature trails, fish, and relax along Harding’s Beach nearby the Stage Harbor Light. The 7,604-acre Monomoy National Wildlife Refuge features kid-friendly trails alongside exhibits and hands-on games at the visitor center, while the protected off-shore portion, a seal habitat and migratory bird path, is a collection of salt and freshwater marshes.
Overlooking Lighthouse Beach and Nantucket, the noble Chatham Lighthouse, an active US Coast Guard station, winks at the Atlantic sailors, among other maritime charms that draw summertime tourists for a sojourn. Aspire to spree through chic boutiques and art galleries along the winding Main Street with historic inns, white-steepled churches, and trendy eateries, or explore the circular coves and miles of saltwater inlets via kayak. The Chatham Historical Society’s Atwood House Museum boasts a collection of 3,000 paintings, decorative arts, and maritime artifacts, like over one hundred nautical charts from the 19th century. From the upcoming 4th of July Parade to the Chatham Christmas Stroll, the First Night fireworks at Oyster Pond follow the traditional "Dropping of the Cod” at midnight. There's no wrong time to visit the local fishermen and sneaky seals along the historic fishing pier, like this summer for a Friday night Chatham Band concert under the lamp-lit glow of Kate Gould Park.
Great Barrington
Settled in 1726 and incorporated in 1761, Great Barrington gained momentum as an essential supporter of the US Revolution. Having experienced recent growth and revitalization thanks to wealthy investors, this gorgeous township in Berkshire County, an "old soul" at heart, proudly displays its past through a number of significant sites wrapped up in natural splendor. With something for everyone to enjoy in between the historic touchstones, the Benedict Pond Loop is minutes west, while the Pfeiffer Arboretum at Long Pond offers another quiet spot to connect with nature via an under-a-mile walking loop through forest and wetland. Drowned by the stunning landscape and nature preserves, the Housatonic River tumbles by the dog-friendly Fountain Pond State Park and south through the heart of town.
To the west, Beartown State Forest features wildlife viewing around a fishing pond and all-season hiking trails, as well as winter snow sports. When the flakes fly, Butternut Ski Area and Tubing Center is a local tradition with over 10 acres, 11 lifts, and artificial snowmakers on all trails for skiing, snowshoeing, and family fun along the snowy slopes. Visitors can dart through the "apres" scene in between shopping ops and dining, like Bogies, a delicious pub and restaurant. Xicohtencatl Restaurant is as eclectic as its name, with colorful decor and patio seating to nourish a mole margarita over weekend live music. With one month of summer remaining, take the opportunity for a hike through the sprawling East Mountain State Park, a spectacular nature preserve to visit this summer, with the Tom Leonard Lean-To Appalachian Trail just south of the main entrance.
Lexington
Having ranked 4th out of 13,000 among America's top small cities by WalletHub, Lexington offers to get a bite of its best experiences. Visitors can taste the good quality of life and affordability over fine dining, shopping, and an iced coffee at Ride Studio Café, a quaint local bike store, as the perfect jumpstart. Journey through history via the award-winning Liberty Ride Trolley Tour, touching a number of Revolutionary War sites between here and Concord. Not your average small town but a giant in the world of literature, Lexington sowed the creative seed in top American writers such as Louisa May Alcott, Ralph Waldo Emerson, and Nathaniel Hawthorne. Featuring a number of 18th-century buildings and the Lexington Battle Green, where the first shot of the American War of Independence was fired in 1775, the historic Battle Road is a popular trail among runners, walkers, and horseback riders. The stately building of Framingham State University, built in 1893, was the nation's first public teaching college.
Why not dine like President Washington circa 1789 at the 1735 Munroe Tavern, where the retreating Redcoats met reinforcements from Boston? Used as a field hospital after the battles of Lexington and Concord, its beautiful colonial-style garden continues to delight patrons with a variety of blooms. The Minute Man, one of the oldest war monuments in the US, looks like the commanding John Parker during the Battle of Lexington. Lexington's artistic flair extends to the lively downtown area, with gourmet restaurants like Artistry on the Green for delicious seared sea scallops among high-end boutiques, jewelry stores, and unique gift shops. In addition, Pine Meadows and Stone Meadow Golf feature a driving range and lessons by professionals. Afterwards, score something at Petra for an evening at the famous Lexington Symphony Orchestra. Before taking off, MA France Gourmet is a must-stop for a chat with the owners about the Bordeaux region and to stock up on French favorites.
Melrose
Melrose, a settlement since the mid-18th century, blends busy city life with a peaceful landscape between open space, forested areas, and conservation land. Ranked 6th in America according to the aforesaid WalletHub report, its quaint downtown dates back to 1900 with grand old homes around the Ell Pond, with something for everyone on a quick escape, just seven miles from Boston! Visitors can soak up the historic charm over window shopping, dining, and nature walks through parks and fields, with an uncrowded feel despite 30,000 locals and under five square miles in area. The unique neighborhood spirit preserves its frontier atmosphere of "rural exurbia" through exquisite Victorian buildings from the late 1800s coexisting with modern facades like accommodations, shopping, and entertainment.
From recreation to cultural facilities, the active Melrose Massachusetts Television is impressively 100 years old, while the exquisite Melrose Symphony Orchestra is a sight to see and experience over a performance. Flaunting a natural heart, the central Ell Pond is a large, trail-lined reservoir with courts, a dog park, a pretty church, and nearby shops like Bohemian Coffeehouse, Molly's Bookstore, and the Bread Shop. In addition to being ringed by a “green belt,” the city flaunts a canopied streetscape as the notion of a garden city, with the Middlesex Fells Reservation to the west, two golf courses, and a state-of-the-art baseball stadium, Morelli Field. Don't miss the historic Wright's Tower, made of stone, at the eponymous park just southwest. Across the town, families enjoy a visit with the animals at Stone Woo, including bears and big cats, as well as a petting area for kids.
Nantucket
Only 30 miles off the Cape Cod southern coast, Nantucket inspires a "little lost world" destination, which is something almost every big, bustling city dweller craves. Just a quick, scenic ferry ride away, welcome to one of the “best islands in the world,” according to National Geographic, an idyl of windswept beaches—never overcrowded—and picture-perfect lighthouses, among other "nuances." The translation as “the Faraway Land” from the native Wampanoag tribe language is quite fitting for the 14-mile-long by 3 1/2-mile-wide crescent-shaped, pristine island with over 40% of daunting natural beauty, including plentiful public beaches. Nantucket's slower pace actually encourages visitors to taste life, savoring every moment on a leisurely getaway, whether swimming, surfing, boutique shopping, fishing, or fresh seafood dining.
Discover how an Englishman, Bartholomew Gosnold, first sighted the island in 1602. Settled in 1659, with many whales off shore through the late 1600s, it served as one of North America's major whaling ports for nearly a century until 1840. After the 1880s decline, Nantucket turned to tourism, successfully becoming a mecca thanks to its everlasting natural beauty, preserved and conditioned along varying terrain for every tase of adventure, like sand dunes, salt marshes, and craggy bluffs. The authenticity, sprinkled with first-rate attractions, accommodations, and restaurants, makes it virtually impossible to take a bad photograph, and no getaway is complete without at least one of the following: walking among the narrow rows of wood-paneled houses and biking to a lighthouse, with a bunch ringing the island to enjoy a panoramic sunset behind your favorite one.
Rockport
While Rockport was founded in the 1600s, abandoned, and re-founded in the 1700s at the northeast tip of Cape Ann, the Agawam Indians called this tribal land home for some 10,000 years! Today, the small town is a big-time destination for outdoor recreation thanks to its prime geography, fine dining, and sunsets at Halibut Point. Home to an active fishing fleet, visitors can hike along trails by the historic granite quarries and observe the authentic harbor town life of fishermen and lobstermen by the docks. From the surrounding woodlands to the coastal trails, visitors can enjoy the blend of terrain over adventures, sightseeing, and fascinating history steps away from your stunning stay at Emmerson Inn, which offers its own pristine slice of Massachusetts coastline to chill out. Hikunset. Flaunting an intriguing past, discover how a gang of 200 women led by Hannah Jumper in 1856 destroyed anything containing alcohol during “Rockport’s revolt against rum,” which kept Rockport "dry" until 2005.
Inspiring a Rockwell painting, Rockport's unmatched beauty and serenity inspire a thriving artist community with cultural pursuits like Rockport Music’s Shalin Liu Performance Center, the Windhover Center for the Performing Arts, and the Rockport Art Association. Motif #1, one of the world's most-painted and photographed fishing shacks, is a stape. From the charming New England inns and delicious B&Bs to state-of-the-art accommodations, it is easy to feel at ease by the sea, with quick access to treasures through gift shops, galleries, candy stores, and clothing boutiques between the beaches for swimming, diving, sailing, and kayaking. Hike out along the jutting Bearskin Neck from the heart into its charming harbor at sunset. The picturesque seaside village also enjoys easy access to Thatcher Island, just off the coast, to explore the Thatcher Island National Wildlife Refuge, home to nature as it was a millennium ago.
Stockbridge
Nestled up against Lenox in the Berkshires, this western Massachusetts gem infused Norman Rockwell's creations with memories from his childhood spent here. Bursting in history and nature, visitors can enjoy charm aplenty, including the one and only Berkshire Botanical Garden, a 15-acre flower-filled space with manicured beds, ponds, and gardens for strolls, picnicking, exhibits, and events amid scented blooms and greenery. Don't miss the nearby Mount, author Edith Wharton's turn-of-the-century estate with tours and frequent cultural events. Nearby, the spacious Naumkeag is a 19th-century summer home with public landscaped grounds. Follow the summertime crowds to the sizeable Stockbridge Bowl for lakefront recreation, and from there, it is just a stroll to the fantastic sunset views from Olivia's Overlook or an evening performance at the iconic Tanglewood venue.
Visitors can browse the Norman Rockwell Museum for his memorabilia and stop by the Berkshire Theatre Group for a modern play. Also home to Chesterwood, the 19th-century summer residence of sculptor Daniel Chester French, this town feels like a living postcard, evoking a sense of nostalgia and warmth. Blessed with surrounding mountains for fresh air hikes and skiing, the Housatonic River through the heart attracts summertime visitors to the lush banks with historic landmarks. Cross the Butler Bridge for the best water views and a selfie, while the Mission House is the former home of an 18th-century missionary and an artifact-filled Native American museum. Reflecting a timeless beauty in every season, the holiday glow on Stockbridge Main Street at Christmas resembles Rockwell's famous painting, plus caroling and cheers.
As one of the earliest English colonies with a vital role in the American Revolution, visiting Massachusetts can be nature-centric, relaxing, or cultural. "Fleets" of boaters come to sail the open waters and kayak along the rugged coastline. From the scenic mountain trails to the coastal bluff hikes, "apres" is sprinkled throughout the streets. There's no wrong time for an enriching escape in the Bay State, where fun, sightseeing, and discoveries leave everlasting memories, filling up your Instagram feed.
Escape it all into Nantucket's daunting island nature, with beaches and lighthouses surrounding a bevy of shopping, sites, and the freshest seafood at the historic heart. From Chatham's balloon festival at Kate Gould Park to the merriment of Stockbridge Main Street at Christmas in the Berkshires, the air is permeated with New England vibes. So whether you choose a town officially graded among the best in America or a blind pick, it only takes a heartbeat to feel the charm work its magic.
