Massachusetts is the place where English settlers first imagined remaking their homeland in a wilderness they called New England. For all their English orientation, they called the great bowl of a bay between Cape Cod and the mainland after the coastal “Massachusett” tribe, then took the bay’s name for the Massachusetts Bay Colony. The towns of Plymouth, Salem, and Boston – all founded 1620–30 – were the beachhead from which the rest of New England was colonized. As the state with the first college, the first democratic government, the first rebels to defy the king, the first authors to invent an American literature, and the first sailors to open the ports of Asia to the West, Massachusetts can claim that much of what matters about New England happened here first. The state’s progressive attitudes and its concentration of colleges and universities keep it on the cutting edge of science and culture to this day.
Boston is nicknamed “the Hub,” not just because all New England roads do eventually lead here, but because Bostonians think of their home as central to all things historical, intellectual, and cultural in the region. Rightly so; Boston’s history is inevitably the lead tale in the anthology of New England’s development. As the largest city and the cultural capital, it is the logical place to begin or end a tour of New England (for further details see Historic Boston).
English explorer Bartholomew Gosnold literally put Cape Cod on the map in 1602 when he named the long curl of land for the fish so abundant in its waters. Cape Cod’s soils are but 15,000 years old – composed of the sand and gravel that mark the southernmost advance of the last glacier – and it is hardly terra firma; every large storm subtly reshapes the shoreline, making peninsulas into islands and vice versa. Yet the very transience of Cape Cod is part of its allure.
Almost equidistant from Boston to the east and New York City to the south, the Berkshire Hills of western Massachusetts pledge a wavering allegiance to both. But the Berkshires is a valley kingdom unto itself. Its busy summer social schedule revolves around the performing arts, but the concentration of resident artists and performers guarantees a rich off-season as well.
In the popular imagination, Salem is the city that tried and executed witches. But the 1692 trials are best regarded as an aberration in the history of this vibrant, entrepreneurial city blessed with the magnificent art of the Peabody Essex Museum and a rich maritime history recounted at the Salem Maritime National Historic Site. In the early days of the country, Salem’s merchant princes were richer than the national treasury. Their magnificent houses still attest to their power and glory.
Lowell was the first purpose-built city in the US, constructed in the 1820s as a large-scale factory town to manufacture textiles with equipment designs adapted from British mills. The textile industry is gone, but the canal network and looming mills remain as testament to America’s first engagement with the Industrial Revolution (for further details see Lowell National Historic Park, MA). After you’ve soaked up the mill history, visit Jack Kerouac Park (part of Lowell National Historical Park) to pay your respects to the Beat author who was a native son.
Settled in 1640, this deepwater port at the mouth of Buzzards Bay has always wrested its living from the sea. In the 1840s, pinemasted whaling barks would tie up at the wharves to offload precious whale oil from a three-year journey (for further details see New Bedford Whaling National Historical Park). Today that same harbor creaks with great iron fishing boats that dredge the bay for scallops, haul flounder from Nantucket Shoals, or venture far offshore for cod and haddock. Somehow the sea air tastes saltiest here.
The opening skirmishes of the American Revolution, in what is now Minute Man National Historical Park, forever link these neighboring towns. More than words of war, Concord also gave the US its first literary voices in Ralph Waldo Emerson (1803–82) and Henry David Thoreau (1817–62). Other writers and thinkers who called Concord home include novelists Nathaniel Hawthorne (1804–64) and Louisa May Alcott (1832–88), who grew up in Orchard House. All of the above are buried at Concord’s Sleepy Hollow Cemetery.Ralph Waldo Emerson House • 28 Cambridge Tpk., Concord • 978 369 2236 • Open mid-Apr–Oct: 10am–4:30pm Thu–Sat, 1–4:30pm Sun • adm
Covering 100 sq miles (259 sq km) yet only 7 miles (11 km) off the mainland, the flounder-shaped island of Martha’s Vineyard is big enough that you’ll want a car to explore its very different communities. Up Island – the rustic western end – is a serene natural world that includes the sacred striped clay banks of Aquinnah. Down Island – the bustling eastern end – has the town of Vineyard Haven, the old whaling port of Edgartown, and the camp-meeting resort of Oak Bluffs.
Plymouth calls itself “America’s home town,” as it was the first English settlement in New England and home of the Separatists, who became known as Pilgrims. The living history museum of Plimoth Plantation depicts the settlement circa 1627, and also has exhibits devoted to Wampanoag life in the same era. History is marked with a statue or plaque on almost every corner of pleasant modern Plymouth. Pilgrim Hall Museum displays artifacts of the original Pilgrims, and addresses some distortions of their story.Pilgrim Hall Museum • 75 Court St., Plymouth • 508 746 1620 • Open Feb–Dec: 9:30am–4:30pm daily • adm • www.pilgrimhall.org
In contrast with Martha’s Vineyard, only residents bother to bring a car to tiny Nantucket, as the island lies 30 miles (48 km) offshore and transport is expensive. Even residents tend to bicycle everywhere (tourists on scooters are scorned). Explore venerable gray-shingled Nantucket town on foot, stopping first at the whaling museum. Then bike out to Wauwinet to hike the dunes at Great Point, to ’Sconset to see rose-covered cottages, or Surfside to swim or fly kites on the beach.
Salem exhibits mixed feelings about its witch history. On the 300th anniversary of the 1692 hysteria that led to the hanging of 19 “witches” and crushing of another, the city erected a solemn memorial to the victims. But come Halloween, Salem is “witch city,” capitalizing on its sensational past to draw curious visitors.
Start your 13-mile (21-km) jaunt through American history by taking your bike with you on the T to the Alewife terminus of the Red Line. Follow well-marked signs to the Minuteman Bikeway, a flat, paved path. Pedal through Arlington, then watch for egrets, herons, and bobolinks along the edges of Great Meadows nature area. The bikeway soon passes the Lexington visitor center of Minute Man National Historical Park, perfect for a rest stop. Pick up the park map and brochures, taking note of historic Lexington Green, your next stop. Make a silent salute to the iconic Minute Man statue on the green, then pedal a few blocks up Bedford Street to enjoy big deli sandwiches at Neillio’s Gourmet Kitchen.
Just west of Lexington Green you switch from the Minuteman Bikeway to Battle Road Trail, an unpaved road for walkers and cyclists that parallels the route of the running battle as British forces retreated in 1775; historical signposts explain the significance of sights along the way. North Bridge, near another visitor center in the park, is especially evocative. At the end of the trail, follow signs to The Wayside and Orchard House to learn about Concord’s 19th-century literary history. Lexington Rd. takes you into Concord Center, where you and your bike can return to Boston on the commuter rail.
Sticking 30 miles (42 km) out to sea on Cape Ann, Gloucester’s busy harbor is a legendary fishing port and home to Rocky Neck Art Colony.
Iconic Motif #1, a red fishing shed in the harbor, is among the most-painted subjects in this lovely village filled with art galleries and boutiques.
Settlers braved frequent Indian raids for the rich soil of the Connecticut Valley. Deerfield preserves 60 buildings from the 17th and 18th centuries.Historic Deerfield • The Street, Old Deerfield • 413 774 5581 • open mid-Apr–Nov: 9:30am–4:30pm daily; Dec–mid-Apr: call for hours • adm • www.historic-deerfield.org
Once your kids have climbed on the Dr Seuss statues at the Quadrangle off State St., take them to visit the nearby history, art, and natural science museums.800 625 7738 • www.springfieldmuseums.org
The vibrant cultural life of Pioneer Valley revolves around four colleges, including Smith, with its major art museum (for further details see Smith College Museum of Art, Northampton, MA). Literary history abounds, as the Emily Dickinson Homestead attests.
Drive Route 2 west from Greenfield over the Berkshire Mountains to North Adams to be wowed by some of New England’s best fall foliage. Turnoffs lead to orchards and sugar houses.www.mohawktrail.com
The long sands of Crane Beach in Ipswich and the winding tidal river at Essex make these North Shore communities tops for nature lovers. Both are renowned for local shellfish.
Its fantastic concentration of grand Federal-style homes makes Newburyport an essential stop for history buffs and preservationists. Birders flock to Plum Island at harbor mouth for some of New England’s best birding.
Worcester has a first-rate art museum and a unique museum of arms and armor, the Higgins Armory.Higgins Armory • 100 Barber Av., Worcester • 508 853 6015 • 10am–4pm Tue–Sat, noon–4pm Sun • adm
New England’s rural heart bustles three times a year with Brimfield antiques shows. Old Sturbridge Village re-creates rural New England of 150 years ago.
Arrive early if you want to see the sleek northern-Italian styling of the Via Matta bar. At night it’s packed with beautiful people sipping cocktails and munching bruschetta.79 Park Plaza
Ever wonder where geniuses unwind? Every day from 4–6pm the bar at this posh Cambridge restaurant offers $1 oysters on the half-shell. There’s also a breezy riverfront patio with great city views.Royal Sonesta Hotel, 40 Edwin Land Blvd., Cambridge
This intimate room with fine acoustics is widely acclaimed for presenting some of the best jazz in the US.Charles Hotel, 1 Bennett St., Cambridge
This Bohemian bar-café programs live jazz by local artists. The imaginative bistro menu is complemented by craft beers and exotic cocktails.541 Tremont St.
Nationally-known comics from HBO, Showtime, Comedy Central, MTV, and the like headline at Boston’s longest-running comedy club.100 Warrenton St.
Built in Ireland, then shipped to Boston and re-assembled, the Kinsale is an authentic piece of the old sod. There’s live music on Tuesday and Saturday.2 Center Plaza, Cambridge St.
If you follow underground music, you are probably already aware of this legendary venue for new bands looking to break through.472–480 Massachusetts Ave., Cambridge
Fresh herbs, hand-chipped ice, and specialty liqueurs place this utterly hip bar in the vanguard of the cocktail world. Bartenders ask your mood then improvise a drink.348 Congress St.
One of sports-crazy Boston’s top game-watching spots is built into the walls of Fenway Park. With an entire wall covered with flat-screen TVs, there’s always, well, a game on.82 Lansdowne St.
The famed performance chain sticks to its Boston roots with this cavernous venue.15 Lansdowne St.
If cuisine is art, chef-owner Ken Oringer is its Picasso. Plan on a long, sumptuous evening.370-A Commonwealth Ave., Boston, MA • 617 536 7200 • Closed L, Sun • over $65
Whether you crave a hot dog with cheese, a bowl of onion soup, or coq au vin with buttered noodles, great Parisian comfort food awaits.468 Commonwealth Ave. • 617 375 0699 • $25–$40
At least a dozen varieties of oyster are available here, with sparkling and mineral-rich white wines to match.550 Tremont St. • 617 423 0550 • $50–$65
French country cooking with contemporary panache uses local meat, produce, and seafood.553 Tremont St. • 617 423 2700 • Closed L, open Sun brunch • over $65
Home of the wildly popular gourmet burger. Local chef Tony Maws follows a no-exceptions policy on local, seasonal, and organic ingredients.853 Main St. • 617 497 5511 • over $65
Come here for impeccable prix-fixe French haute cuisine with a New England twist.774 Boylston St. • 617 351 2037 • over $65
Hit dishes at this colorful joint include grilled fish with fiery salsas, BBQ-pulled pork, and ice-cold oysters washed down with margaritas.1271 Cambridge St., Cambridge • 617 491 6568 • Closed L, open Sun brunch • $40–$50
The chef-owner of this sophisticated dining room in Harvard Square makes field trips delving into regional cuisines of Italy then magically recreates them with local ingredients.Charles Hotel • 1 Bennett St., Cambridge • 617 661 5050 • Closed L • over $65
A fish-lover’s dream, Mare specializes in Italian coastal cuisines with an eco emphasis.135 Richmond St. • 617 723 6273 • Closed L • $50–$65
This small, rocking restaurant offers a lively bar scene and adventurous food. Neighborhood foodies adore the weekend pajama brunches.647 Tremont St. • 617 226 4600 • Closed L Mon–Fri • $40–$50
Fine French haute cuisine has made this Cape Cod restaurant a legend.2449 Main St., Brewster, MA • 508 896 3640 • Closed Mon, Fri–Sun L, Dec–Apr • over $65
Elegant country dining fit for an English baron with French taste.11 Hawthorne Rd., Lenox, MA • 413 637 0610 • Closed L, Wed • over $65
Enjoy lively seasonal cuisine, sourced locally, and the best wine cellar in New England. Bargain monthly wine dinners pair courses with wines from a single producer.160 Pawtucket Blvd., Tyngsboro • 978 649 4400 • Open for B, L, D daily, brunch Sun • over $65
Cutting-edge casual cuisine with a raw bar of Westport shellfish and succulent wood-grilled local meats and fish. The outdoor bar is the most convivial summer social scene on Massachusetts’ south coast.1 Bridge Rd., Westport • 508 636 6500 • Closed Mon–Fri L, Jan–Mar • $50–$65
In an idyllic waterfront setting, dine on Beef Wellington, skillet-roasted halibut, or buttered lobster with tortellini in a truffle emulsion.120 Wauwinet Rd., Nantucket • 508 228 0145 • Closed late Oct–Apr • over $65
The contemporary French menu of seafood and vegetables and the Bordeaux-dominated wine list betray the owner’s Gallic origins.63 Circuit Ave., Oak Bluffs, Martha’s Vineyard • 508 696 0200 • Closed L, Mon–Wed May & Sep–Oct, Nov–Apr • over $65
The French-trained chef-owner offers sumptuous bistro fare – grilled strip steak, duck breast with apples, and seafood stew.197 E. Main St., Gloucester • 978 282 4426 • Closed L, Mon, Sun Sep–May, Jan • $50–$65
The elegant Northern Italian menu changes frequently, depending on the New England harvest and the fishermen’s catch. There’s an extensive wine list.888 Main St., Waltham • 781 894 2234 • Closed L, Sun • $50–$65
Really taste the Berkshires at this local favorite where the chef offers a superb bar menu of classic bistro dishes.10 Castle St., Great Barrington • 413 528 5244 • Closed L, Sun (Nov–Jan) • $40–$50
Celebrity chef Ming Tsai’s home kitchen blends Asian and Western influences in light, spicy, innovative dishes.585 Washington St., Wellesley • 781 283 5790 • Closed Sun L • over $65