Boston is the best of both worlds, a vibrant cosmopolitan city that’s also very traditional. Founded in 1620 by Puritan colonists from England, Boston is one of America’s oldest cities. A walk in any direction reveals the shrines of the American Revolution shoulder-to-shoulder with modern office buildings joined most recently by a visionary revitalization of the waterfront.
There is no denying that Boston is history proud. But it is also a center of culture with unparalleled museums, world-class music, dance, and theater, as well as standout shopping. And as home to more than 50 colleges and universities in addition to several world-renowned hospitals, Boston can rightfully stake a claim as an intellectual and medical capital.
More than ever before, one of the great pleasures of visiting Boston is the dining (and drinking) scene. For downtown dynamism, try the Seaport District, which offers a profusion of chef-driven restaurants that highlight fresh, local ingredients. For laid-back glamour, consider drinks or late-night dining in the trendy South End.
Across the Charles River, Cambridge is a separate city, and in many senses a world apart from Boston. Anchored by Harvard and MIT, the “People’s Republic of Cambridge” is a bustling student enclave of bookstores, ethnic eateries, art-house cinemas, and bars.
The number of side-trip-worthy attractions just outside of Boston is truly astonishing. It’s a good thing that Boston’s subway system—called the “T”—links many of the suburbs to downtown. Tree-shaded Brookline is an affluent streetcar suburb with a large Jewish community (lots of good bagel shops and delis here) and is the childhood home of John F. Kennedy. Next door, Newton is a patch of low-key restaurants, independent shops, and abundant green space that allows residents to enjoy the benefits of village living within just a few minutes of the city.
As the T stretches north from the city, Somerville is undergoing gentrification in Davis Square, where Tufts University students and hipsters mix with townies at quirky watering holes and ethnic restaurants. Medford, Everett, and Revere are all within trolley-stop distance of downtown, offering plentiful recreational activities: hike at Middlesex Reservation in Medford, rock-climb in Everett, and swim in the ocean at Revere Beach. Though even farther north, Stoneham has a fine small zoo.
Within the Route 128 belt north and west of the city, Watertown, Waltham, Arlington, and Belmont are each just minutes from Boston (and from each other), offering entertainment, restaurants, and specialty shopping within vibrant and walkable downtown districts. To the south, football and soccer fans routinely trek the 20 miles from downtown (via Dedham and some very fancy strip malls) to visit Foxboro’s singular attraction—Gillette Stadium.
Known as “the heart of Massachusetts,” Worcester County is the geographic center and the largest county in the state, encompassing a swath of mostly agricultural farmland and hilly forest. Worcester County effectively separates the state between Boston—and, as Bostonians will tell you, “western” Massachusetts—the Berkshires and everything else in between.
Worcester is the region’s largest city and its county seat. The Nipmuc tribe, or “people of the freshwater pond,” were the first known inhabitants of this area. The name perhaps refers to Lake Quinsigamond, the narrow four-mile-long lake that is one of Worcester’s most prominent geographical features (the other being its seven hills). The first English settlement was established here in 1673 and was called Quinsigamond Plantation. Driven out by the Nipmucs during King Philip’s War in 1698, the English didn’t resettle the area until 1713. The settlement was then incorporated as a town and named in honor of Worcester, England. The British way has survived to this day; here Worcester is properly pronounced “Wuss-ter.”
By 1828 the opening of the Blackstone Canal and the building of the Boston & Worcester Railroad brought manufacturing—first textiles, then steel wire—to the city. The city’s many cultural and educational institutions, including the Worcester Art Museum, Mechanics Hall, and Worcester Polytechnic Institute, were established as a result of the prosperity that followed. Today, Worcester’s principal industry is education. The city is home to 10 college and universities, among them Holy Cross, Worcester Polytechnic Institute, Clark University, and UMass Medical School. Undeniably, the college students give Worcester a youthful vibe (and better bars and restaurants).
Beyond Worcester the landscape offers wooded countryside punctuated by towns large and small. To the south, experience early-19th-century New England life at Old Sturbridge Village, a re-created historic settlement. Head north from Worcester and there are under-the-radar sites that charm: Rural Boylston is home to the Tower Hill Botanic Garden, and the mill town of Clinton draws visitors from around the world to its Museum of Russian Icons.
In Leominster, in the far northern reaches of Worcester County, folk hero and roaming pioneer apple orchard farmer John Chapman, popularly known as Johnny Appleseed, was born in 1775. Follow the Johnny Appleseed Trail along Route 2 from Harvard to Orange. It’s an area for leaf peeping, country drives, and as you would expect, lots of apple orchards.
North of Boston encompasses both the historic Merrimack Valley outside the city and the towns that extend along the curve of coast northward to the New Hampshire border.
Just 20 miles northwest of Boston, the quaint, quintessentially white-clapboard New England towns of Lexington and Concord saw some of the first military action of the American Revolution. Lexington’s Battle Green and Concord’s Old North Bridge at the Minute Man National Historic Park are the principal sites for the events that took place on April 19, 1775. For fans of American literature, Concord has additional appeal. By the 19th century, Concord was the center of the transcendentalist movement and home to some of New England’s greatest writers. For visitors the town has a seemingly endless supply of historic literary house museums to explore: Ralph Waldo Emerson’s house, Nathaniel Hawthorne’s Wayside, Henry David Thoreau’s Walden Pond, and Louisa May Alcott’s Orchard House. To the north, roughly follow the Concord River to the industrial city of Lowell. In a town renowned as the “City of Spindles,” the mill buildings that line the banks of the Merrimack River make up the Lowell National Historic Park and attest to the city’s role in the shift from farm to factory in America’s Industrial Revolution.
The Salem witch trials of 1692 made Salem famous—notorious in fact—but Salem is much more than witches. Salem’s Maritime National Historic site tells the story of the city’s development as a major seaport and the Peabody Essex Museum houses an impressive collection of art and other spoils from the far reaches of the globe.
Forty miles north of Boston, the city of Gloucester and the towns of Manchester-by-the-Sea, Essex and Rockport make up the Cape Ann peninsula, which is sometimes referred to as the “Other Cape.” Gloucester is a legendary fishing port with family-friendly beaches. Manchester-by-the-Sea’s Singing Beach is perfect for a sunset stroll. Essex is famed for its antique shops, tidal flats, and fried clams while Rockport’s Bearskin Neck shops and restaurants are a good destination if you are feeling spendy. Beyond Cape Ann, stretching almost to the New Hampshire border, the towns of Ipswich, Newburyport and Plum Island are comparatively remote with extensive unspoiled shoreline that attracts nature lovers to enjoy serene beaches and the blissful solitude of wildlife sanctuaries.
Sandwiched between the Berkshire Mountains to the west and the Quabbin Reservoir to the east, the rural Pioneer Valley is a vast three-county swath of fertile farmland and country villages, vibrant college towns, and the industrial city of Springfield.
The Connecticut River bisects the region from the Vermont border in the north to the Connecticut River in the south. It was the river that first brought English colonists to the Pioneer Valley around present-day Springfield in 1635. These settlers really were pioneers, as this frontier formed the westernmost border of the state until the 1720s.
Less well-known than the Berkshires and far less populated than adjacent Worcester County, the Pioneer Valley offers family-friendly attractions, a cluster of lesser-known specialty museums, and ample natural scenery.
Springfield is best known as the home of the Basketball Hall of Fame and it is the prime reason for families to visit the region. But there is such an abundance of kid-centric sights—including Six Flags New England, the Forest Park Zoo, and the Dr. Seuss National Memorial—that you could spend a couple days in Springfield and leave begging for more.
The Pioneer Valley has an unparalleled concentration of higher education institutions, known as the Five College Consortium. It includes the flagship campus of the University of Massachusetts and four colleges: Amherst, Mount Holyoke, Smith, and Hampshire. The five campuses are located in neighboring towns that are all within 10 miles of each other and together they offer visitors access to museums, public lectures, and sporting events in inviting college environs. Amherst is the liveliest of the towns; it is home to UMass, Amherst, and Hampshire. The campus of Smith College is located in Northampton. Dubbed Noho, it has an interesting mix of academics and artists, and a large gay and lesbian community, along with eclectic restaurants and quirky shops that align perfectly with the town’s free-spirited culture. South Hadley (home to Mount Holyoke) is the most isolated (and quietest) of the college towns, but orchards and farmland have their charms.
To the far north, follow the Mohawk Trail, America’s First Auto Road, as it parallels the Deerfield River. Just off the highway, a sense of nostalgia permeates the small town of Deerfield with its tree-lined Main Street and perfectly preserved historic district. Spend a morning or afternoon here, and you’ll get the feeling that you may have just stepped back in time.
The mountainous region of far western Massachusetts is hardly an undiscovered vacation spot. After all, since the mid-1800s the Berkshires has been a popular summer enclave that has attracted writers, artists, musicians, and the wealthy. They came to the Berkshires for inspiration, for the cool mountain breezes, for a reprieve from the city heat, and to enjoy the region’s sylvan beauty.
Today the Berkshires are a vacation destination for everyone. The rolling hills and mountain ranges are still largely unspoiled, offering spectacular views and lots of outdoor recreational opportunities. In summer the arts scene abounds with world-class music, theater, and art. In the fall the forests blaze with color; in winter the mountain slopes lure skiers; and in spring there is maple sugaring and a burst of green nearly everywhere.
Lenox is the most resort-like town in the Berkshires. It is the home of Tanglewood, the famed summer music festival of the Boston Symphony. Lenox is hugely popular with the Tanglewood crowd for its stellar restaurants, lovely shops, and genteel country inns. Neighboring Stockbridge is also home to Tanglewood (the campus straddles both towns) but is decidedly quainter. As painted by Norman Rockwell—who lived here from 1953 until his death in 1978—Stockbridge is small-town America.
But the Berkshires also has a crunchy, outdoorsy vibe, nowhere more so than in Great Barrington. The Old Trinity Church, immortalized in the song Alice’s Restaurant, is now the Guthrie Center, a community music hall. Great Barrington is also popular with vacation homeowners from New York, making this one of the few places in Massachusetts where a Yankees hat is tolerated. Nearby, the tiny village of Sheffield draws avid antiquers who hunt for undiscovered treasures in the shops along Route 7.
Located in the center of Berkshire County, bustling Pittsfield is the largest community in the Berkshires—really a bona fide city. Pittsfield has redefined itself as a cultural center with its restored Colonial Theater, lively art galleries, and new eateries. Continue north to Williamstown, home to prestigious Williams College and its Williamstown Theatre Festival. And funky North Adams has lately experienced an influx of young contemporary artists who have made the city their home.
The salty-fresh waters of the Atlantic, warm sand between your toes, an abundance of homemade ice cream stands, and wind-weathered fried clam shacks. Cape Cod and the “Islands”—Martha’s Vineyard and Nantucket—offer visitors a summer vacation that is as laid-back as it gets.
The Cape itself is a 62-mile-long arm-shaped peninsula that juts out into the Atlantic. Technically the Cape is an island, separated from the Massachusetts mainland by the man-made Cape Cod Canal and connected by the heavily trafficked Sagamore Bridge to the north and the only slightly less congested Bourne Bridge to the south. But endure the bridge traffic and you’ll realize that the drive is worth it.
Each of the Cape’s 15 charmingly distinct towns offers vacation opportunities for both explorers and strollers. At 400 square miles, the Cape is much bigger than most outsiders realize. So it is helpful to know the lay of the land. The Upper Cape refers to the towns closest to the bridges, including Falmouth and Sandwich. To the east, in the mid-Cape region, is Hyannis, famed as the summer home of the Kennedy clan. In practical terms, Hyannis is the transportation hub of the Cape. The Cape’s major airport is here; so, too, the bus and railroad stations, while both Martha’s Vineyard and Nantucket ferries as well as a veritable flotilla of whale-watch boats and fishing charters leave from Hyannis Harbor. The mid-Cape town of Yarmouth draws young families for its warm Nantucket Sound beaches, minigolf, and fast-food eateries. Lower Cape towns include affluent Chatham, with its picturesque lighthouse and postcard-perfect Main Street, and to the north, Brewster on Cape Cod Bay, historically known as the “Sea Captain’s Town.” Eastham doesn’t have a defined center, but it is the gateway for the Cape Cod National Seashore, which for many defines the essence of the Cape—a 40-mile swath of sun-drenched, pristine Atlantic beach backed by marsh and dunes. The outer Cape towns of Wellfleet and Truro are known for their art galleries, while funky, bohemian Provincetown is a leading gay resort and has all the local color that you would ever want to see.
Across Nantucket Sound, Martha’s Vineyard and Nantucket are both very special ports of call. Both islands are far less developed than the Cape: places of unrelenting beauty with fine, unspoiled beaches. The Vineyard is the bigger of the islands—it’s nearly 100 square miles—and at 7 miles and a quick 35-minute ferry ride—it’s a lot closer. Nantucket is a true island getaway destination. The name itself is a Native word that means “the land far away.” Once the foremost whaling port in the world, today Nantucket sees yachts fill its harbor. Before or after dinner, stroll along the waterfront and select your dream boat.
The South Shore is a geographic region that extends south of Boston from Quincy to Plymouth along the shores of Massachusetts Bay and Cape Cod Bay. Often ignored by tourists in a hurry to get down to the Cape, both Quincy and Plymouth offer historically significant sites. Just 10 miles south of the city, Quincy (pronounced Kwin-zee) is known as the “City of Presidents,” where at the Adams National Historic Park you can visit the birthplace and homes of John Adams and his son John Quincy Adams. In Plymouth see the sites familiar to every American schoolchild as the birthplace of the first Thanksgiving: Plimoth Plantation, the Mayflower II, and Plymouth Rock.
Between Quincy and Plymouth, the string of pretty coastal towns—Hull, Hingham, Cohasset, Scituate, and Marshfield—are affectionately known by locals as the “Irish Riviera.” In the early part of the 20th century prominent Irish-Americans like Mayor James Michael Curley and John F. Fitzgerald (President Kennedy’s grandfather) built seaside summer homes here; true-blue union members soon followed. The area makes an outstanding summer side trip with excellent beaches and terrific seafood. On a hot summer Sunday, Hull’s Nantasket Beach and its carousel still draw Bostonians just as they have since the middle of the 19th century. Hingham is a mecca for high-end shopping and chichi dining. Cohasset is a find with its cute seaport village—if it looks familiar it may be because many scenes from The Witches of Eastwick were filmed here. While in Scituate you can stroll the cove-like harbor and watch the lobster boats come in with the day’s catch. And Marshfield’s landscape of pristine salt marshes, dunes, and miles of gorgeous ocean beach puts the focus on the water with swimming, boating, and fishing.
Not to be confused with the South Shore, south coastal Massachusetts encompasses the extreme southwest corner of the state, bordered by Buzzards Bay and Rhode Island. Venture to New Bedford, where whaling flourished in New England in the mid-1800s. Large numbers of immigrants came from the Azores and settled in New Bedford after being recruited as whalemen along the way. Today New Bedford is home to the largest commercial shipping fleet on the East Coast, the country’s largest Portuguese-American community, and a restored historic wharf district. To the south, in Westport, the waves at Horseneck Beach make it a favorite among visitors and surfers alike. Another 8 miles takes you to Fall River, which capitalizes on its industrial past and is home to Battleship Cove, the world’s largest collection of naval ships from World War II.