Chilmark & Menemsha
Occupying most of the western side of the island between Vineyard Sound and the Atlantic, Chilmark is a place of pastoral landscapes and easygoing people. Chilmark's chief destination is the picture-perfect fishing village of Menemsha, where you'll find shacks selling seafood fresh off the boat.
Welcome to the towniest town in the Berkshires. A main street, both cute and gritty, runs through the center, curving to cross some railroad tracks. On it you'll find a hardware store, a bar and a few places to eat including a proper diner favored by politicians desiring photo ops with working-class folks.
The 'falls' in Fall River are what drove this town's development back in the 19th century, when the river fueled several textile companies and an ironworks, earning the place the nickname Spindle City. After the decline of the textile industry, and a devastating city-wide fire in 1928, the once prosperous town never really regained its footing.
The village of Tyringham, between Lee and Monterey, is the perfect destination for an excursion into the heart of the countryside. Once the home of a Shaker community (1792–1874), Tyringham is now famous for its Gingerbread House. Surrounding the tiny village center, scenic back roads snake over gentle hills and past farmland.
Mt Greylock State Reservation
At a modest 3491ft, the state's highest peak can't hold a candle altitude-wise to its western counterparts, but a climb up the 92ft-high War Veterans Memorial Tower at its summit rewards you with a panorama stretching up to 100 verdant miles, across the Taconic, Housatonic and Catskill ranges, and over five states.
Cape Cod National Seashore
Cape Cod National Seashore extends some 40 miles around the curve of the Outer Cape and encompasses the Atlantic shoreline from Orleans all the way to Provincetown. Under the auspices of the National Park Service, it's a treasure-trove of unspoiled beaches, dunes, salt marshes, nature trails and forests.