Escapes from New York: The Best Road Trips from NYC

The drive: 3 hours from most parts of New York City
Why you're going: Music, museums, and mountain vistas
Stay overnight? Definitely

Set in the heart of the Berkshires, Lenox is home to the legendary Tanglewood music festival and within easy driving distance of the Norman Rockwell Museum, the Williamstown Theatre Festival, Jacob's Pillow Dance Festival, and contemporary art powerhouse Mass MoCA. Lenox is a bucolic, quintessentially New England town with such an unusually rich cultural scene that one could spend four to seven days here without running out of things to see and do.

The drive: 1.5 hours
Why you’re going: Wineries and beaches 
Stay overnight? Not necessarily

You may have never heard of gewürztraminer, but many rank the dry white wine that's grown in this area as one of the best in the world. It's just one of the many varietals one can sip in this burgeoning wine region, where three tastings can usually be had for about $10. It you're not the tippling type there's still much to see and do on this spit of land at the eastern end of Long Island. That includes swimming, lighthouse climbs, picking one's own berries or lavender at a local farm, and more. And if you want a lifestyles-of-the-rich-and-famous experience, duck over to the South Fork, where homes belonging to Steven Spielberg, Martha Stewart, and dozens of other bold-faced names are located in the famous Hamptons.

The drive: Around 4 hours
Why you’re going: Sailing, sightseeing, and seafood chowder
Stay overnight? Unquestionably

Since its founding, Newport has lived large. It was a maritime center to rival New York and Boston in its early years, and became a playground for tycoons in the 19th century. Today you’ll find eye-candy architecture in downtown's colonial, Federal, and Victorian houses, many of which are now cute B&Bs, shops, and restaurants. Facing the sea are rows of so-called “cottages”—actually mind-bogglingly opulent mansions built by the Vanderbilts and their peers, who employed the top architects of the day to create structures rivaling the palaces of Europe. Vacationers often spend the morning touring these mansions before claiming a spot at one of the lovely beaches nearby or on the deck of a sailboat. You can either charter a vessel or take a pleasure cruise open to the public.

Pictured: Architect Richard Morris Hunt's masterpiece The Breakers. 

The drive: 1.5 hours (same time via the Metro-North Railroad)
Why you’re going: Contemporary art, hiking, fishing, and swimming
Stay overnight? Not necessarily

Beacon has two secular patron saints: folk singer Pete Seeger and artist Robert Irwin. The latter helped turn a former Nabisco factory into a blockbuster museum, Dia:Beacon. He thought big—the facility has a hall the size of a football field to house Dan Flavin’s light sculptures, along with monumental works by Richard Serra, Michael Heizer, and other contemporary masters. Dia's presence encouraged a raft of small galleries to open in Beacon, turning it into an art mecca. But the town has a pristine natural side, thanks to activist Seeger, who lived here and was able to get local politicians to protect and clean up waterways and forest areas. This is a wonderful spot for fishing, hiking, and cooling off in good old-fashioned swimming holes. And if you’re an insatiable art hound, you could detour to take in the outdoor sculptures at the rustically beautiful Storm King Art Center in nearby Mountainville.

The drive: About 3 hours (there's also a bus that takes 4 hours)
Why you're going: Unspoiled nature 
Stay overnight? That would be best.

This is the part of the Jersey Shore that has nothing to do with Snooki. Instead, it's all about escaping pop culture and immersing oneself in nature. The Wetlands Institute protects 6,000 acres here, and the nearby Stone Harbor Bird Sanctuary is another peaceful preserve. But even on the public beaches, the sands are wonderfully serene (perhaps because alcohol is forbidden). 

The drive: Roughly 2 hours (about 1.5 hours on Amtrak) 
Why you're going: American history, great museums, food
Stay overnight? Stay a few nights

It might seem odd to trade one city for another, but Philly has a very different vibe than the Big Apple. Though both have important early American historic sights, in Philadelphia the past is front and center. And seeing the Liberty Bell, Independence Hall, Ben Franklin’s residence, and other sites is a thrill. The same could be said of Philadelphia’s resplendent galleries (particularly the Philadelphia Museum of Art and the Barnes Foundation). At the end of the day, you have the choice of an ooey, gooey, and utterly satisfying cheesesteak (perhaps at Geno's, pictured above), or gourmet fare. Philly has all this and more—but is far more laidback than New York.

The drive: This one takes a 6.5-hour commitment.
Why you're going: Francophone culture
Stay overnight? Stay a few nights

You haven’t left North America, but it may feel like you have when you’re wandering through Montreal’s cobbled old city, with its centuries-old stone buildings, soaring cathedral (pictured), and the touristy horse-drawn carriages that clip-clop to and fro. The city’s absorbing museums, raging nightlife, and top-drawer culinary scene convince most visitors to linger for a few days. 

The drive: About 2 hours (take the train or a bus to get you there in 3)
Why you're going: Antiquing, historic sights, museums, country lanes, quaint towns
Stay overnight? Not necessarily

The best way to do Bucks County is to meander. That way you’ll really be able to soak in the charm and quirkiness of this corner of Pennsylvania. For many years, it was a place for artists’ colonies; lyricist Oscar Hammerstein II and novelists Pearl Buck and James Michener all lived in the area. You’ll want to stop at Doylestown's Mercer Museum and Fonthill Castle (pictured), the eccentric, self-built creation of Arts and Crafts movement luminary Henry Chapman Mercer. Nearby is the Moravian Pottery and Tile Works, the factory he founded to preserve the craft of handmade ceramic tiles.  It is still in operation today. Not too far away is the fabulous James A. Michener Art Museum, a treasure trove of 19th- and 20th-century American art, housed in a former prison. All around are quaint towns (like New Hope) with boutique-lined main streets, historic homes, galleries, regional theaters, and, if you visit during the right season, meadows awash in wildflowers. 

The drive: About 2 hours
Why you're going: Mountain views, affordable prices, golf, skiing, hiking
Stay overnight? You betcha

Take a road trip to the Catskills and you're following an example set by generations of New Yorkers before you. As anyone who ever saw the movie Dirty Dancing knows, this was one of the region's top resort communities for many generations. It’s not hard to see why. Though only 100 miles from New York City, the mountains are genuinely pastoral, with a relatively sparse population. That’s partially because a quarter of a million acres were declared “forever wild” by the New York State Constitution. As you drive through, you'll see forested peaks, rolling meadows, prized trout streams, and lush golf courses—not strip malls. And while most of those shuffleboard-in-the-AM, comedy-show-at-night resorts are gone, they’ve been replaced by refreshingly affordable inns, B&Bs, and farm-to-fork restaurants.