Massachusetts is where English settlers first imagined remaking their homeland in a wilderness they called New England. For all their Englishness, they named the bay between Cape Cod and the mainland after the coastal Massachusett tribe, then took the bay’s name for their colony. The towns of Plymouth, Salem, and Boston were the beachhead from which the rest of New England was colonized. As the state with the first college, first democratic government, first rebels to defy the king, first authors to invent an American literature, and the first sailors to open the ports of Asia to the West, Massachusetts claims that much of what matters about New England happened here first. The state remains a pioneer of science and culture to this day.
New England’s largest city, Boston is nicknamed “the Hub,” not just because all New England roads do eventually lead here, but because Bostonians think of their home as the center of all things historical, intellectual, and cultural in the region. Rightly so; Boston’s history is inevitably the lead tale in New England’s development (for further details see Historic Boston ).
Almost equidistant from Boston to the east and New York City to the south, the Berkshire Hills pledge a wavering allegiance to both. But the Berkshires is a valley kingdom unto itself. Its summer social schedule revolves around the performing arts, but the concentration of resident artists guarantees a rich off-season as well (for further details see Berkshires, Massachusetts ).
The fish-shaped island of Martha’s Vineyard covers 100 sq miles (259 sq km) yet is only 7 miles (11 km) off the mainland. 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.
Settled in 1640, this deepwater port at the mouth of Buzzards Bay has always wrested its living from the sea. In the 1840s, pine-masted whaling barks would tie up at the wharves to offload whale oil from a three-year journey (for further details see New Bedford Whaling National Historical Park, New Bedford, MA ). Today that harbor creaks with great iron fishing boats that dredge the bay for scallops, haul flounder from Nantucket Shoals, or venture offshore for cod and haddock.
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 around 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 their story.
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 shore, making peninsulas into islands and vice versa. Yet the very transience of Cape Cod is part of its allure (for further details see Cape Cod, Massachusetts ).
Lowell was the first purpose-built city in the US, constructed in the 1820s as a large 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 the country’s first tryst with the Industrial Revolution (for further details see Art Museums ). 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.
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 transportation is expensive. Even residents tend to bicycle everywhere (tourists on scooters are scorned). Explore venerable gray-shingled Nantucket town on foot, starting at the whaling museum (for further details see Nantucket Whaling Museum, Nantucket, MA ). Then bike to Wauwinet to hike the dunes at Great Point, to Siasconset to see rose-covered cottages, or Surfside to swim or fly kites on the beach.
In the popular imagination, Salem is the city that tried and executed witches. But the 1692 trials are best seen as an aberration in the history of this vibrant city blessed with the 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 grand houses still attest to their power.
The opening skirmishes of the American Revolution, in what is now Minute Man National Historical Park , forever link these neighboring towns. Concord also gave the US its first literary voices in Ralph Waldo Emerson (1803–82) and Henry David Thoreau (1817–62). Also, novelist Louisa May Alcott (1832–88) grew up in Orchard House . All of the above are buried at Concord’s Sleepy Hollow Cemetery.
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 Visitors’ 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. Pay homage to the iconic Minute Man statue on the green, then pedal a few blocks up Bedford Street to enjoy deli sandwiches at Neillio’s Gourmet Kitchen (No. 53).
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 Road 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 harbor is a legendary fishing port and home to Rocky Neck Art Colony .
The vibrant cultural life of Pioneer Valley revolves around four colleges, including Smith, with its major art museum . Literary history abounds, as the Emily Dickinson Homestead on Main Street attests.
Settlers braved frequent Indian raids for the rich soil of the Connecticut Valley. Deerfield preserves 60 buildings from the 17th and 18th centuries.
Once your kids have climbed on the Dr. Seuss statues at the Quadrangle off State Street, take them to visit the nearby history, art, and natural science museums.
The iconic Motif #1, a red fishing shed in the harbor, is among the most-painted subjects in this lovely village of art galleries and boutiques.
Drive Route 2 west from Greenfield over the Berkshire Mountains to North Adams to be wowed by some of the area’s best fall foliage. Turnoffs lead to orchards and sugar houses.
The sands of Crane Beach in Ipswich and the winding tidal river at Essex make these North Shore communities great for nature lovers. Both are known for 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 the harbor mouth for some of New England’s best birding.
Worcester has a top art museum and a unique indoor-outdoor museum, the EcoTarium.
New England’s rural heart bustles thrice a year with Brimfield antiques shows (for further details see Brimfield, MA ). Old Sturbridge Village re-creates rural New England of 150 years ago.
Supreme musicianship and elaborate picnics are equally characteristic of the Boston Symphony’s summer home.
Film and TV directors and actors come here to hone their stagecraft; celebrity-spotting is a summer sport in town when the festival takes place.
Famed for their Shakespeare performances, this company also develops and produces new plays of social and political significance.
A wellspring of new plays and musicals, Barrington Stage incubates electrifying theater that often winds up playing on Broadway.
Home is a former fish-packing plant adjacent to Rocky Neck Art Colony. Award-winning playwright Israel Horowitz is a company co-founder.
Humor, passion, a sense of the absurd, and a sharp political edge are hallmarks of this small troupe.
America’s oldest professional summer theater puts on classics, comedies, mysteries, and musicals.
The 1888 Stockbridge Casino by noted architect Stanford White makes a grand setting for new, classic, and contemporary theater.
Enjoy performances by leading US and international dance companies in a magical setting.
This harborside pavilion is a dynamic venue for various performers.
Part gastropub and part music venue, The Sinclair serves bistro comfort fare as indie bands, Americana musicians, and hipster songwriters entertain.
This intimate room that boasts excellent acoustics is widely acclaimed for presenting some of the best jazz in the country.
This Bohemian bar-café programs live jazz by local artists. The creative bistro menu is complemented by craft beers and exotic cocktails.
Some of the country’s leading mixologists craft the cocktails in this classy Kenmore Square hotel bar designed for intelligent discussion and wistful flirtation.
Nationally known comics from HBO, Showtime, Comedy Central, MTV, and the like headline at this popular spot, which is Boston’s longest-running comedy club (since 1977).
Fresh herbs, hand-chipped ice, and specialty liqueurs place this hip bar in the vanguard of the cocktail world. Bartenders ask you your mood and then improvise a drink.
If you follow underground music, you’re probably already aware of this legendary venue for new bands that are looking to break through.
Built in Ireland, then shipped to Boston and re-assembled, the Kinsale is an authentic piece of the old sod. Live music on Tuesday and Saturday.
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.
The famed chain sticks to its Boston roots with this cavernous venue.
South Boston-raised Barbara Lynch artfully reinvents fine dining at the cusp of French and Italian.
This contemporary Japanese restaurant is celebrated for chef Tim Cushman’s inventive sushi and bounteous omakase .
This small, rocking restaurant offers a lively bar scene and adventurous food. Neighborhood foodies adore the weekend pajama brunches.
Home of the wildly popular gourmet burger. Local chef Tony Maws follows a no-exceptions policy on local, seasonal, and organic ingredients.
Come to L’Espalier for impeccable prix-fixe French haute cuisine with a New England twist.
At least a dozen varieties of oyster are available here, and the sparkling and mineral-rich white wines recommended are a perfect match.
Located on the Rose Kennedy Greenway, Townsman features nose-to-tail locavore cooking in a brasserie setting with late-night bar.
Expect Arab-inspired eastern Mediterranean cuisines at Oleana, featuring spicy dishes from Turkey, Greece, and North Africa. Many diners choose to sit at the outdoor tables in the garden.
Local oysters and crudo plates complement Italian seafood dishes in this chic North End restaurant.
This modern Asian gastropub hits all the marks with Phillip Tang’s skillful blend of East and West.
For a three-course meal for one with half a bottle of wine (or equivalent meal), taxes and extra charges.
€ under 40 €€ €40–60 €€€ over €60
North and South Markets boast dozens of boutiques and specialty shops. Quincy Market has the city’s best food court, as well as more than 40 pushcart vendors selling largely local wares.
Contemporary art, mostly by New England artists, is the focus of deCordova Sculpture Park and Museum. The store at the museum matches that spirit with a range of art supplies, jewelry, wearable art, and inventive educational toys.
This premier museum of fine art in craft media carries an extensive selection of artists’ jewelry, which is displayed alongside work in glass, ceramic, fiber, and wood.
Bargain hunters from all over New England converge on this mall just off I-495, where 170 stores are dedicated to designer apparel and upscale housewares.
It is not difficult to see why this rocky peninsula is such an inspiration to artists. You can walk from cottage to cottage to see (and buy) paintings created by resident painters that belong to one of the oldest operating art colonies in America.
The leading US producer of scented candles offers the world’s largest candle selection, home furnishings, food, entertainment, all-year Christmas shopping, and a candle-making museum.
The museum shop carries faithful reproductions of historic pressed glass from Sandwich, an extensive line of American art glass, and blown glass from the museum’s own on-site glassblowing studio.
More than 30 antiques shops do business in this historic North Shore community. Keep an eye out to find nautical artifacts, Chinese export porcelain, 18th- and 19th-century furniture, and excellent oil paintings.
In summer, Friday is “gallery night” in Provincetown. Galleries along Commercial Street set out wine and cheese to lure prospective buyers.
Two of the largest gatherings of crafts artists and designers in New England take place over Memorial Day (late May) and Columbus Day (mid-October) weekends at the Three-County Fairgrounds in Northampton, an excellent opportunity to explore and buy local crafts.
Local growers provide the meat, produce, and cheeses for this highly adept American bistro.
Great local fish meets Cape Cod veggies to spectacular effect for elegant, candlelit dining.
Enjoy lively seasonal cuisine that is sourced locally, and the best wine cellar in New England.
Really taste the Berkshires at this local favorite which offers a superb bar menu of classic bistro dishes.
In an idyllic waterfront setting, dine on Beef Wellington, skillet-roasted halibut, or buttered lobster with tortellini in a truffle emulsion.
Local vegetables and fish feature on the seasonal menu with French, Italian, and Spanish accents matched by an extensive wine list.
The French-trained chef-owner offers sumptuous bistro fare – grilled strip steak, duck breast with apples, and seafood stew.
The elegant Northern Italian menu changes often, depending on the New England harvest and the fishermen’s catch. Extensive wine list.
Cutting-edge casual cuisine with a raw bar of Westport shellfish and succulent wood-grilled local meats and fish. The outdoor bar is a convivial summer social scene.
Celebrity chef Ming Tsai’s kitchen blends Asian and Western influences in light, spicy, innovative dishes.