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  • The Naumkeag estate in Stockbridge, Massachusetts
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    Stockbridge, Massachusetts: Culture-Filled Town in the Berkshires

  • Lighthouse Point Park in New Haven, Connecticut
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    New Haven, Connecticut: University Center on Long Island Sound

  • A waterfront restaurant in Mystic, Connecticut
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    Mystic, Connecticut: Seaside Village Steeped in History

  • The Federal Hill neighborhood in Providence, Rhode Island
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    Providence, Rhode Island: Artsy Capital City

  • The Gay Head Lighthouse in Aquinnah on Martha’s Vineyard, Massachusetts
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    Cape Cod, Massachusetts: Beaches, Islands and Charming Towns

The Mystic Seaport Museum in Connecticut
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Connecticut Office of Tourism

A Tour of 5 Colorful and Culture-Filled New England Destinations

By Karen Galvin

  • Route distance:
    804.00
  • Suggested Time:
    1-2 weeks

On this intriguing road trip loop of New England, explore vibrant small cities and bucolic towns in Massachusetts, Connecticut and Rhode Island.

With Boston as its gateway, this route will explore the unique cultural, historic and culinary offerings of five of New England’s urban centers and picturesque villages. Leaving Boston, drive into western Massachusetts, then south to Connecticut before looping along the coast to Rhode Island and Cape Cod, finishing back in Boston. Along the way, pause to enjoy cultural attractions, vibrant neighborhoods, mountain vistas, iconic islands and vast beaches.

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The Naumkeag estate in Stockbridge, Massachusetts
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Stockbridge, Massachusetts: Culture-Filled Town in the Berkshires

Fly into Boston’s Logan International Airport and rent a car, then leave the city behind and drive west through rolling hills toward the picturesque Berkshire Mountains of western Massachusetts, stopping in historic Stockbridge. Begin your explorations on Main Street, the charming heart of this picturesque town. The Red Lion Inn, founded in 1773 and visited by presidents and famous authors, and the Stockbridge Library offer clues about the town’s history. Learn about Stockbridge’s most famous former resident at the Norman Rockwell Museum, home to the largest collection of the famed illustrator’s work and his original studio, all in a gorgeous setting overlooking the Housatonic River Valley. History buffs will want to tour Naumkeag and Chesterwood, two splendid country estates that date to the late 1800s. Built by a prominent New York City lawyer, Naumkeag is noted for its large, terraced gardens, landscaped grounds and 44-room country house filled with the family’s artwork. At Chesterwood, tour the Georgian Revival former summer home and studio of famed sculptor Daniel Chester French (among many other works, he designed the huge statue of Abraham Lincoln in the Lincoln Memorial). In the Berkshire Botanical Gardens, visitors will find one of the oldest public display gardens in the Northeast, with sections dedicated to herbs, daylilies, native plants and more. For many in the know, the name “Stockbridge” is synonymous with “Tanglewood” – a famous outdoor music center that draws aficionados from across the region to a full calendar of events including the Boston Symphony Orchestra’s summer festival. Choose the direct route to the next stop – New Haven, Connecticut – or opt for a scenic route, stopping in tiny Great Barrington and other hamlets tucked away in valleys.

180 km
2 hours by car
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Lighthouse Point Park in New Haven, Connecticut
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Connecticut Office of Tourism

New Haven, Connecticut: University Center on Long Island Sound

In New Haven, Yale University isn’t just an Ivy League institution of higher education – it’s also a visitor destination that’s home to museums and art collections well worth seeing. Stroll around campus to discover historic buildings juxtaposed with modern architecture. Marvel at the Gutenberg Bible and John James Audubon’s “Birds of America,” on permanent display at the Beinecke Rare Book & Manuscript Library, and check out the American decorative arts collection in the Yale University Art Gallery. Then get some fresh air – head to East Rock Park, a popular recreation destination where you can see the 1887 Soldiers’ and Sailors’ Monument and take in clifftop views of New Haven and Long Island Sound. In addition to great water views, Lighthouse Point Park also offers nature trails and a historic carousel – take a spin for 50 cents. The park is on a migratory bird flyway, so keep an eye out for cedar waxwings, tree swallows and Cooper’s hawks. Now that you’ve worked up an appetite, sample New Haven’s celebrated take on pizza at Frank Pepe Pizzeria Napoletana or Sally’s Apizza. To delve into the finer points of heaven on a plate, take a pizza tour. In the morning, head east along the Connecticut coast to reach Mystic.

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90 km
1 hour by car
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A waterfront restaurant in Mystic, Connecticut
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Mystic, Connecticut: Seaside Village Steeped in History

Founded in 1654, modern Mystic has a population of less than 5,000, but in the 18th and 19th centuries, it was a significant seaport, with more than 600 clipper ships built there. These days, Mystic is where you’ll find one of Connecticut’s most-visited attractions – the Mystic Seaport Museum, which provides insight into the town’s rich maritime history. Climb aboard the last wooden whaling ship in the world, take a short cruise on the Mystic River on a steamboat or explore on a rented sailboat, rowboat or pedal-powered boat. Back on land, watch blacksmiths, coopers and printers hard at work in the 19th century village. Then head to Main Street, where you can browse in shops, dine on fresh seafood or eat at the original Mystic Pizza restaurant, made famous in the 1988 romantic comedy film of the same name. Work off the pizza with a hike through woodland, wetland and meadow habitats at the Denison Pequotsepos Nature Center, where you can observe rescued hawks and owls. Looking for a little retail therapy? Olde Mistick Village is a shopping and dining destination built in the style of an 18th century village. When you’re ready to hit the road again and head toward Providence, Rhode Island, take a side trip to Narragansett or Newport for lunch and coastal sightseeing.

80 km
1 hour by car
04
The Federal Hill neighborhood in Providence, Rhode Island
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Providence, Rhode Island: Artsy Capital City

With a thriving arts community and vibrant, diverse neighborhoods, Rhode Island’s capital city Providence is a lively place to visit. Two world-class educational institutions set the tone for this city on the Providence River – the Ivy League Brown University and the Rhode Island School of Design, one of the nation’s most prestigious art schools. The RISD Museum is filled with high-quality items made by students and faculty, so the exhibits are engaging and ever-changing. Art in this city isn’t found just inside buildings; take all or part of a 1.5-hour self-guided walking tour to discover public art – both sculptures and murals – across downtown, then explore other neighborhoods. Wander along Benefit Street, admiring its grand architecture from the Colonial and Victorian eras, reflecting the lives of its thriving merchant class dating to the early 1800s. Also take time to explore Federal Hill, Fox Point and other historic and hip neighborhoods. Right downtown, Waterplace Park is famous for the seasonal WaterFire installation, an award-winning series of fire sculptures set on Providence’s three rivers. The installation is best viewed while strolling along Riverwalk’s 1.2 kilometers of cobblestone walkways. Venice-styled pedestrian bridges span the river, and gondola rides are available. It’s a classic way to wrap up your stay in Providence before driving 90 minutes east to the beaches and towns of Cape Cod.

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130 km
1.5 hours by car
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The Gay Head Lighthouse in Aquinnah on Martha’s Vineyard, Massachusetts
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Massachusetts Office of Travel & Tourism

Cape Cod, Massachusetts: Beaches, Islands and Charming Towns

As you head east into Massachusetts, continue driving until you reach Cape Cod, a popular vacation destination where you’ll find a series of quaint beach towns that range from rustic to regal. Take your pick from Falmouth (home to the Woods Hole Science Aquarium), Orleans (with both ocean and bayside beaches), Eastham (featuring the Three Sisters Lighthouses), Truro (a quiet town on the Outer Cape) and Provincetown (a lively town at the tip of the Cape with inns, restaurants and nightlife). Take a whale-watching cruise from P-town, as the locals call it, and dine on fresh seafood. Driving back down the Cape, be sure to stop at Cape Cod National Seashore – it’s a can’t-miss stretch of pristine beaches and woodlands ideal for outdoor recreation. Continue on to Hyannis, where you can visit the John F. Kennedy Museum and jump on a ferry or small plane to visit the coastal islands of Martha’s Vineyard and Nantucket, known for their dramatic beaches, folksy charm and traditional New England architecture. Back on the mainland, drive north to Plymouth, where the Pilgrims landed in 1620. Check out Plymouth Rock and views of Plymouth Harbor at Pilgrim Memorial State Park. Tour Plimoth Plantation, an interactive living museum that re-creates the Pilgrims’ 17th century settlement, complete with costumed role players. To wrap up your road trip, drive to Boston, less than an hour north, and catch your flight home from Logan International Airport.

Official Discover New England Travel Site