8 Best Downtowns In Massachusetts

A great Massachusetts downtown holds four centuries of American life in a few walkable blocks. You can trace the whole country's story down a single Main Street here. Norman Rockwell found his idea of small-town America along the storefronts of Stockbridge. William Stanley switched on the country's first practical AC power in Great Barrington in 1886. Colonial militia and Revolutionary thinkers left their mark on the squares of Concord and Marblehead. Whaling money and fishing fleets built the harbor blocks along the coast at Nantucket and Rockport. These are eight of the best downtowns in Massachusetts.

Great Barrington

Just eight miles south of Stockbridge is Great Barrington. Behind the town's downtown storefronts is the Housatonic River Walk. A gate off Main Street opens onto the half-mile path, which runs streamside within a few steps of the sidewalk and puts herons and canoes in view. The Mahaiwe Performing Arts Center, a 1905 theatre restored for film, concerts, and live broadcasts, runs shows on Castle Street just off Main most nights of the week. A historical marker on Main Street notes where William Stanley ran the country's first practical alternating-current power system in 1886, stringing wires along the street's elm trees to light storefronts for a test run that lasted into that summer. On South Main Street, the Wheeler Farmstead houses the Great Barrington Historical Society Museum. The working homestead built in 1771 now holds more than 50,000 artifacts tracing the town back to its colonial roots.

Stockbridge

Main Street in Stockbridge runs through the aptly named Main Street Historic District. It's a stretch of green lawns, complete with a white church spire, and municipal buildings that Norman Rockwell painted into his 1967 work "Stockbridge Main Street at Christmas." The Red Lion Inn has been open at the eastern end of the street since 1773, serving meals and housing travellers longer than the country has existed. The Mission House, a National Historic Landmark built around 1742, stands at 19 Main Street. The Norman Rockwell Museum sits just outside downtown and holds the world's largest collection of original Norman Rockwell art. The Berkshire Hills rise behind the rooflines on nearly every sightline down Main Street, a green backdrop to the whole downtown for anyone exploring Stockbridge.

Northampton

Located in the Pioneer Valley, Northampton's downtown starts at the Academy of Music, the oldest continuously operating municipally owned theatre in the country. A few doors down, Hotel Northampton has welcomed guests since 1927; its Colonial Revival lobby is still furnished with period antiques from when it opened. A block off Main Street on West Street, you'll find Forbes Library. It's home to the Calvin Coolidge Presidential Library and Museum, and its reading rooms are open to everyone. Smith College's campus spreads out across a large area right off Elm Street, where Paradise Pond and the Lyman Conservatory make for a quiet stretch of greenery and water.

Concord

Concord's Main Street opens directly into Monument Square, where a granite obelisk raised in 1866 memorializes the town's involvement in the Civil War. The Colonial Inn, also in Monument Square, has poured drinks and made beds since 1889. The Concord Museum and Ralph Waldo Emerson's house both sit within a few blocks of Monument Square. A half-mile walk from the square will take you to the Old North Bridge, where Minute Man National Historical Park preserves the ground colonial militia held against British troops in 1775. Trails there follow the Concord River past stone monuments and old gravesites. Two miles further out, you'll reach Walden Pond State Reservation. This is the glacial pond Henry David Thoreau made famous, with a 1.7-mile loop trail circling the water and a public swimming beach open all summer.

Marblehead

Old Town in Marblehead winds along Marblehead Harbour without following a grid. The streets grew out of colonial-era footpaths rather than a planner's straight lines, which gives residents and visitors many angles on the water. The Old Town House, built in 1727, still stands in Market Square as one of the oldest public buildings in continuous civic use in the country. Fort Sewall sits on a rocky point above the harbour entrance, its earthworks open to the public with a clear view out to Marblehead Light, one of the most photographed markers on the North Shore. Between the two, Abbot Hall's clock tower marks the high point of downtown and holds the original "Spirit of '76" painting in its meeting room. Shops, galleries, and inns fill the colonial-era buildings between Washington and State Streets.

Rockport

Downtown Rockport narrows to a literal point at Bearskin Neck, a slim peninsula that pushes out into Rockport Harbour with fishing boats rocking on either side. Main Street tightens into Bearskin Neck's single lane, once used to land the day's catch and ship granite out by barge, now lined with artist studios and seafood counters instead. At the tip sits Motif No. 1, a red fishing shack destroyed in the Blizzard of 1978 and rebuilt that same year as a faithful replica. Visiting artists have painted it so many times over the decades that it earned the nickname "the most painted building in America." Front Beach sits right where Main Street meets the water, close enough that the smell of salt air and the sound of the surf reach the shop doors.

Chatham

Across the base of Cape Cod, Chatham's Main Street runs straight from the rotary at Kate Gould Park down to the water, ending at Chatham Lighthouse and the Fish Pier. The lighthouse, an active Coast Guard station since 1808, has marked the harbour entrance and the elbow of Cape Cod for well over a century, and the beam is still visible from Main Street after dark. A short walk past it takes you to boats unloading the day's catch at the Fish Pier, Cape Cod's largest commercial fishing pier. Watch for the harbour seals that gather in the water below and the gulls that trail the boats in. Back on Main Street, generations-old shops and galleries fill roughly a half mile of storefronts between the rotary and the shore.

Nantucket

From Harwich Port, next to Chatham, the Freedom Cruise Line ferry crosses to Nantucket in under 80 minutes and lands at Straight Wharf right in the middle of downtown. Nantucket's Main Street and the surrounding blocks of Federal and Centre Streets still run over cobblestones laid down in 1836, some cut from stones ships once carried as ballast. The Whaling Museum occupies a restored 1847 candle factory a block from the wharf, home to a 46-foot sperm whale skeleton, a working Fresnel lens, and a rooftop deck looking straight out over the harbour. Brick storefronts and captains' houses from the whaling era line several streets off Main.

Eight Downtowns, Eight Different Days

These eight downtowns cover a lot of ground. In Chatham you get a working fishing pier and a Coast Guard lighthouse, and in Concord a glacial pond and a Revolutionary battlefield sit within a couple of miles of Monument Square. Nantucket pairs a walk over 1836 cobblestones with a forty-six-foot whale skeleton inside the Whaling Museum. The draw might be a waterfront, a battlefield, a theatre, or a row of colonial storefronts. Each of these towns is worth an afternoon on your next trip through Massachusetts.