Founded in 1623 by English fisherfolk, Gloucester is one of New England's oldest towns. This port, on Cape Ann, has made its living from fishing for almost 400 years, and it has inspired books and films like Rudyard Kipling's Captains Courageous and Sebastian Junger's The Perfect Storm. And despite some recent economic diversification, the town still smells of fish.
The patriarch of Cape Cod towns, Chatham has a genteel reserve that is evident along its shady Main St: the shops are upscale; the lodgings, tony. That said, there's something for everyone here – families flock to town for seal-watching, birders migrate to the wildlife refuge. And then there are all those beaches.
In a region famous for its charming college towns, you'd be hard-pressed to find anything more appealing than the crooked streets of downtown Northampton. Old red-brick buildings and lots of pedestrian traffic provide a lively backdrop for your wanderings, which will likely include cafes, rock clubs and bookstores (which explains why locals call their town 'NoHo').
Crowd-pleasing beaches, a terrific bike trail and the quaint seaside village of Woods Hole are the highlights of the Cape's second-largest town. Falmouth puffs with pride over its most cherished daughter, Katharine Lee Bates, who wrote the words to the nation's favorite patriotic hymn, America the Beautiful.
On April 18, 1775, British troops marched out of Boston, searching for arms that colonists had hidden west of the city. The following morning, they skirmished with Colonial minutemen in Lexington, then continued on to Concord, where the rivals faced off at North Bridge, in the first battle of the War of Independence.
Shoot. You're in Springfield. This recession-hit town has certainly seen better days, but there are some surprises here that might just make you glad you came. Downtown, you'll find some striking reminders of the city's 19th-century wealth, including a handful of quality museums, a grand symphony hall and stately Romanesque Revival buildings at Court Sq.
Welcome to 'Worm Town,' as locals affectionately call their city. A wealthy manufacturing center during the industrial revolution, this place invented and produced barbed wire, the modern envelope and more. Worcester has struggled mightily since factories began shutting down after WWII, with scant urban renewal victories in recent years.
Art galleries, primo surfing beaches and those famous Wellfleet oysters lure visitors to this seaside village. Actually, there's not much Wellfleet doesn't have, other than crowds. It's a delightful throwback to an earlier era, from its drive-in movie theater to its unspoiled town center, which has barely changed in appearance since the 1950s.
This quintessential college town is home to the prestigious Amherst College, a pretty 'junior ivy' that borders the town green, as well as the hulking University of Massachusetts and the cozy liberal-arts Hampshire College. Start your explorations at the town green, at the intersection of MA 116 and MA 9.
Odds are, this ferry-port town – where the lion's share of summer day-tripping boats arrive – will be your introduction to the island. Welcome to the Vineyard's summer fun mecca: a place to wander with an ice-cream cone in hand, poke around honky-tonk sights and go clubbing at night.