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The Best Road Trips From New York City

From the east end of Long Island to the City of Brotherly Love, these road trips don't disappoint.

New York is the city that never sleeps, but sometimes we could sure use a rest. When the breakneck pace of the Big Apple has you caught up in a whirlwind, a trip out of town can be the best way to recalibrate. Fortunately, there are numerous road trip destinations that offer whatever you’re looking for. Nature, relaxation, culture – they’re all just a short drive away.

Greenport, N.Y.

The bucolic North Fork of Long Island is known as being the low-key alternative to its buzzier and busier sister Fork to the South. This is epitomized by the charming town of Greenport. Popular attractions at the seaside destination include a historic movie theater and antique carousel, as well as numerous museums, art galleries, restaurants, and, when it’s time to settle in, a host of inviting boutique hotels.

As delightful as Greenport is, the drive there will be even better. You’ll be in the middle of Long Island’s wine country – acres upon acres of green dotted with one winery after another. If you plan to sample the fruits of the land on your tour, make sure to designate a driver.

Montauk, N.Y.

Should you instead opt for a trip to Long Island’s southern perch, don’t stop driving until you reach The End. While upscale hotels and restaurants have elevated Montauk from pure surfer-town to chic destination over the past several years, it is still decidedly more laid back than the rest of the Hamptons scene.

Visitors can relax at the town’s beautiful beaches and ocean fronts, go fishing, surfing and paddling, and enjoy the plethora of seafood restaurants, nature trails and festivals. Of course, a visit to the historic Montauk Point Lighthouse is always a must. And don’t avoid Montauk just because it’s the off-season. The town is great to visit all year long.

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Newport, R.I.

Rhode Island’s popular seaside city is known for its opulent past. Visitors can tour the magnificent mansions that were once the summer retreats of the Astors and Vanderbilts. For a more modern experience, take a scenic boat ride around the harbor or a picturesque stroll along the Cliff Walk. Add in some incredible seafood and this Ocean State city becomes and ideal getaway locale.

The four-hour drive from New York City will take you along the Connecticut coast. Make a pit stop at one of the region’s many historic towns to enjoy a quintessential New England experience of picture-perfect scenery and exciting attractions.

The Catskills

Roughly three hours outside New York City, the Catskills are a verdant mountain region, ideal for any type of getaway.

The Catskills are famous for its extensive number of well-maintained hiking trails. There are 98 peaks, so you’ll have plenty of paths to choose from.

No matter the time of year, Windham Mountain Resort has something for everyone – skiing, golfing, live concerts, and relaxing spa treatments are just a few of your options. The region is also teeming with wineries and breweries in case you’re in the mood to imbibe.

road trips for convertibles

Beacon, N.Y.

Just an hour north of Manhattan sits the quaint town of Beacon, smack dab in the middle of the Hudson Valley. The drive there – north along the Hudson River with picturesque views – doesn’t get much better. Once you arrive, you can choose between strolling Main Street’s mile-long drag of shops, cafes, or restaurants. Or, if you’re an outdoorsman, go for a hike or kayak down the Hudson.

One can’t-miss tourist attraction is Dia: Beacon. Opened in 2003 in a former Nabisco box printing factory, the museum presents the Dia Art Foundation’s collection of art from the 1960s to the present as well as special exhibitions and public programs. Depending on when you’re in town, you may also be able to catch a minor league baseball game.

Philadelphia, Pa.

If it’s not a change of pace you’re looking for but just a change of scenery, you could do a lot worse than Philadelphia. The City of Brotherly Love is unmatched in its historic pedigree. Must-see landmarks include Independence Hall, where both the Declaration of Independence and U.S. Constitution were signed, and the Liberty Bell.

The iconic “Rocky” steps beckon all to the Philadelphia Museum of Art, but don’t forget to go inside. The museum houses more than 200,000 pieces of art from Claude Monet, Georgia O’Keeffe, Andy Warhol and many others.

No trip to Philadelphia is complete without a proper cheesesteak. Head to Geno’s or Pat’s to get yours.

The Berkshires, Mass. 

Nearly 100 years ago, the Boston Symphony Orchestra was invited to play a three-concert series in the Berkshires. Ever since, the region, which encompasses Western Massachusetts, has been a cultural hotspot. Aside from the orchestra’s annual summer residency at the Tanglewood Institute, other popular cultural attractions include the Norman Rockwell Museum, the Massachusetts Museum of Contemporary Art, the Clark Art Institute and the farmhouse where Herman Melville wrote “Moby Dick.”

But there are plenty of things to do outside the walls of museums and auditoriums. Adventure parks, water sports, fishing, horseback riding, camping, biking, and hiking – including along the Appalachian Trail – are all available.

What’s your favorite Northeast road trip destination? Tell us in the comments below!

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Comments
  • Kevin A.

    Just went to Salem, MA, for the day. What a wonderful day trip! A lot of driving and a lot of traffic but October is the perfect time to visit. Halloween everything! Food, vendors, tours, what a great day!!!

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