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').
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, this 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.
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.
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.
Tall, white church steeples rise above ancient oaks, elms and maples in colonial Concord, giving the town a stateliness that belies the American Revolution drama that occurred centuries ago. Indeed, it is easy to see how writers such as Ralph Waldo Emerson, Nathaniel Hawthorne, Henry David Thoreau and Louisa May Alcott found their inspiration here.
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.
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 favorite daughter, Katharine Lee Bates, who wrote the words to the nation's favorite patriotic hymn, America the Beautiful.
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.
At the northern tip of Cape Ann, Rockport is a quaint contrast to gritty Gloucester. Rockport takes its name from its 19th-century role as a shipping center for granite cut from the local quarries. The stone is still ubiquitous: monuments, building foundations, pavements and piers remain as a testament to Rockport's past.