14-Day Northeast USA Road Trip Itinerary

The northeast offers epic road-tripping on a miniature scale: a few hours behind the wheel can take you from sea level to the highest point in the northeastern United States. Along the way, duck into picture-postcard towns for clam shacks, craft beer, and maple syrup shots; collect covered-bridge and lighthouse selfies to shore up your Yankee cred. It’s not all small-town life—in Portland, Providence, and Boston, soak up the history and culture that keep New England a creative hotbed.  

DAYS 1 AND 2: PHILADELPHIA 

Start your whirlwind trip in the Cradle of Liberty. Devote your first morning to exploring Independence National Historical Park. The two most popular sights are Independence Hall (where the Constitution and Declaration of Independence were signed) and the Liberty Bell Center.

But don’t neglect the Independence Visitor Center, where you must make a reservation (March through December) to tour Independence Hall. If you have extra time, visit the Benjamin Franklin Museum on Franklin Court. Have lunch at the nearby Reading Terminal Market. In the afternoon, you can stay in Old Town to see more historic sights, including the Carpenter’s 

Hall, Christ Church, the Betsy Ross House, and Elfreth’s Alley, or you can delve deeper into the Constitution at the National Constitution Center or the American Revolution at the aptly named Museum of the American Revolution. At night, dinner and nightlife beckon in nearby Center City. 

Devote Day 2 to Philly’s art and museums. Philadelphia Museum of Art on Benjamin Franklin Parkway, followed by lunch in the museum’s lovely dining room, will be enjoyable to almost anyone; it’s the city’s widest-ranging art museum. But if your interest is Impressionist, Postimpressionist, and early modern American art, the Barnes Foundation may be a better destination (reservations required).

In the afternoon explore one of Philadelphia’s distinct neighborhoods. Stroll around Rittenhouse Square and stop in at the Rosenbach Museum and Library, which has a diverse collection ranging from the original manuscript of James Joyce’s Ulysses to the works of beloved children’s author Maurice Sendak. There’s also Society Hill, 

Queen Village, and South Philadelphia for the Mummer Museum on 9th Street and the outdoor Italian Market. Set aside time to dine in one of the city’s best restaurants or take in a concert. 

DAYS 3, 4, 5: NEW YORK CITY 

You could spend weeks in New York and not scratch the surface of all there is to see and do in the Big Apple, but you’ll need three days minimum to see the big sights. Begin your first day at the Empire State Building or Top of the Rock, taking in the panoramic view of the city. Next head up to the Metropolitan Museum of Art. 

You could easily spend a whole day here, but you’ll exhaust yourself if you do. Luckily, just behind the museum lies beautiful Central Park, where you can relax on a bench, rent a rowboat, or explore a meadow and watch the world go by. Exit the park’s south end at 5th Avenue and work your way downtown, browsing the department stores and shops that abound. If you’re there at dusk, walk instead south on 7th Avenue toward the bright lights of Times Square and catch a Broadway show. On Day 2 seek out some history via a ferry trip to the Statue of Liberty and Ellis Is- 

land. You can beat the crowds with any early start. Allow yourself about six hours if you plan to do a thorough visit with guided tours. If not, you can be back in Manhattan by lunchtime. After lunch, stroll through the Wall Street area, home of the colonial-era Fraunces Tavern, mid-19th-century Trinity Church, and St. Paul’s Chapel, Manhattan’s oldest surviving church building.

Also here is the World Trade Center site, complete with time line and memorial. Just north are the neo-Gothic Woolworth Building (don’t miss the splendid gilded lobby) and City Hall. Hop on the N or R train to 8th Street, where you can stroll around Washington Square Park and Greenwich Village. 

On your last day in town, do what many New Yorkers do on their days off— wander. Make your way to Chinatown for a dim sum breakfast or tapioca-filled soft drink. From here head north to SoHo and Nolita for galleries, chic boutiques, and restaurants.

If you haven’t eaten by now, hit a café a few blocks north in the happening East Village, home to yet more shops and vintage stores. From Union Square, walk up Broadway to the fashionable Flatiron District with its inimitable Flatiron Building. Take a break in Madison Square and soak up the surrounding skyline. Have dinner in one of the neighborhood’s noted restaurants.  

DAY 6: NEW HAVEN, CT 

Wake up and head to New Haven, Connecticut. The Constitution State’s second-largest city is home to Yale University, named for British shipping merchant Elihu Yale. Take an hour-long walking tour with one of the university’s guides and feast your eyes on the iconic Gothic-style structures that adorn the campus.

After you’ve worked up an appetite, a stop for New Haven–style pizza is a must. Less than a mile from campus are two institutions known for thin-crust pies cooked in brick ovens: Pepe’s Pizzeria and Sally’s Apizza. For the burger enthusiast, there’s Louis’ Lunch on Crown Street. Spend the night in town.  

DAY 7: PROVIDENCE, RI 

Get an early start, and head north on Interstate 95 to make your way toward Providence. Rhode Island’s capital holds treasures like Benefit Street, with its Federal-era homes, and the RISD Museum of Art at the Rhode Island School of Design. Be sure to savor a knockout Italian meal on Atwells Avenue in Federal Hill—Pane e Vino is a popular choice. For dessert, it’s hard to top the cannoli at Scialo Bros. Bakery. If you’re visiting in early June, sample authentic eats from all over Italy, while live music fills the streets, during the Federal Hill Stroll. Spend the night in a downtown Providence hotel for easy access to sights and restaurants. 

DAYS 8 AND 9: BOSTON, MA 

A short drive north on Interstate 95 will bring you to Boston, New England’s cultural and commercial hub. To savor Boston’s centuries-old ties to the sea, take a half-day stroll past Faneuil Hall and Quincy Market or a boat tour of the harbor. 

From the Boston Common, the 2.5-mile Freedom Trail links treasures of America’s fight for independence, such as the USS Constitution (better known as “Old Iron-sides”) and Old North Church (of “one if by land, two if by sea” fame).

Be sure to walk the gas-lighted streets of Beacon Hill, too, pausing on Acorn Street for an iconic photograph. Boston’s North End is home to Paul Revere’s Home, and has great Italian dining options like Antico Forno and cannolis from Mike’s Pastry. At night, order chowder and Sam Adams at Union Oyster House or a nightcap at the Liberty Hotel’s Clink bar. 

The following day, either explore the massive Museum of Fine Arts and the grand boulevards and shops of Back Bay, perhaps heading to the Isabella Stewart Gardner Museum to take in some world-class art in a palatial setting. Or visit colorful Cambridge, home of Harvard University and the Massachusetts Institute of Technology (MIT). Lively Harvard Square is a perfect place to do some people-watching or catch a street performance; the All Star Sandwich Bar is an excellent choice for lunch. 

DAYS 10 AND 11: PORTLAND, ME 

From Boston, hit the road early and drive two hours to Portland, Maine, stopping in Portsmouth, New Hampshire, or Ogunquit Beach to stretch your legs if you wish. Spend the day exploring Maine’s largest city, its historic neighborhoods, shopping and eating lobster rolls in the Old Port (which has a great craft beer scene), or visiting one of several excellent museums. A brief side trip to Cape Elizabeth takes you to Portland Head Light, Maine’s first lighthouse. From Portland, it’s easy to add on an extension to Acadia National Park if you have another day to spare.  

DAY 12: WHITE MOUNTAINS, NH 

In the morning, pass thick forests broken by glassy lakes as you drive west to Lincoln, New Hampshire, home of the beautiful White Mountains. Spend a day exploring the Flume Gorge in Franconia Notch or leaf-peeping on a drive through Kancamagus Highway.

Spend the night at Omni Mount Washington Resort, recalling the glory days of White Mountain resorts. Beloved winter activities here include snowshoeing and skiing on the grounds; you can even zipline. Afterward, defrost with a cup of steaming hot cider. 

DAYS 13 AND 14: STOWE, VT 

Next, set out for the village of Stowe. Its proximity to Mt. Mansfield (Vermont’s highest peak at 4,395 feet) has made Stowe a popular ski destination since the 1930s. If there’s snow on the ground, hit the slopes, hitch a ride on a one-horse open sleigh, or simply put your feet up by the fire and enjoy a Heady Topper (an unfiltered, hoppy, American Double IPA).

In warmer weather, pop into the cute shops and art galleries that line the town’s main street and sample some of the finest cheddar cheese and maple syrup that Vermont has to offer. Rejuvenate at Topnotch Resort, which offers more than 100 different treatments. Spend your last two nights here, taking optional excursions to the Ben & Jerry’s Factory or to nearby Shelburne Farms, Lake Champlain, or Burlington before you bid adieu to the Northeast.

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