21 Great Day Trips

Come out of winter-hibernation mode, hop in the car, and enjoy a change of scenery at one of our favorite regional destinations.


Edit ModuleShow Tags

Hudson, NY

This Rivertown’s working-class grit has given way to a progressive artistic spirit. The stroll-worthy main street is laden with antique stores (more than 50!), art galleries, on-trend restaurants, performance spaces, elegantly appointed B&Bs, and historic buildings.

Woodstock, NY

Were it not for its rich cultural pedigree, and its connection (however tenuous) to the festival of the same name, Woodstock might resemble any other charming Upstate New York town. But, beyond the Village Green, where tourists gather and old hippies still strum guitars, lies a treasure trove of galleries, restaurants, shops, and theaters.

New Canaan, Norwalk, & Westport, CT

Contemporary art and creative cuisine thrive in this little corner of Connecticut. Three cities — New Canaan, Norwalk, and Westport — make for a doable one-day itinerary with plenty of culture and good eats to make the most of the mileage.

Albany, NY

In addition to its rich history (it’s the oldest continuous settlement of the 13 Colonies), our state capital also happens to have thriving arts-and-culture and food-and-drink scenes. And unlike New York City, you won’t have to deal with the crowds and parking nightmares.

Stockbridge, MA

Unwind amid the bucolic splendor of the Berkshires, birthplace of Norman Rockwell’s quintessential New England.

Hyde Park, NY

Hyde Park packs a powerful dose of history and culture into one ZIP code. Renowned as the birthplace of President Franklin Delano Roosevelt and home to various Vanderbilts (plus The Culinary Institute of America), it’s a fun place to watch the past come alive.

New Hope, PA

At only one square mile, this charming Delaware River town boasts a hodgepodge of tempting restaurants, colorful shops, and historic (as well as purportedly haunted) sites dating back to the American Revolution.

Queens, NY

When it comes to the outer boroughs, Brooklyn gets most of the love. But Queens (just one stop on the 7 train from Grand Central) is worthy of a serious second look. If you focus on Long Island City and Astoria — two of the hippest and closest-to-the-city neighborhoods — you can easily put together a food-and-culture-filled day. Bonus: no driving!

Mystic, CT

A beloved aquarium, an adorable village, historic ships and a pizza place made famous by one of Julia Roberts’ earliest movies are all part of the charm of Mystic. It’s a home-run destination for a quick day of family fun.

Quick Picks

New Windsor, NY 

From White Plains: 55 minutes

A trip here offers two guarantees: fresh air and 3D beauty at the Storm King Art Center. A mountain of the same name and a larger-than-life interactive art garden (almost two miles long!) are the area’s two biggest draws, each replete with plenty of hiking and walking trails cutting swaths through stunning scenery.

Bear Mountain State Park, NY 

From White Plains: 40 minutes

A day trip here is chock-full of fun. Visit Trailside Museums & Zoo; ride the merry-go-round; rent a boat on Hessian Lake; or hike the mountain to its summit. Bear Mountain Inn offers indoor dining, while picnic groves dot the park grounds.

Westhampton, NY 

From White Plains: 1 hour 45 minutes

The closest of the Hamptons is totally doable for a day trip. Get an early start, and you’ll have plenty of time to hit the beach, grab a stellar Neapolitan pie at Pizzetteria Brunetti, shop Main Street, and dine among an impressive collection of Warhol silkscreens at Starr Boggs

Nyack, NY 

From White Plains: 20 minutes

Nyack’s street fairs are the stuff of legend. But indulge your senses anytime: Enjoy restaurants, galleries, and unique shops (ranging from art and fashion at Maria Luisa to tarot readings at Mind Over Matter) on Main Street and Broadway, silhouetted by the Hudson River.

Warwick, NY 

From White Plains: 1 hour

Heading here? Be ready to window-shop and eat. Main Street and its surrounds abound with eateries and shops. Venture to nearby Bellvale Farms Creamery for the best ice cream. From March through October, the Warwick Drive-In Theater shows first-run movies on three screens. In fall, it's one of the best places in New York for apple picking. 

Ocean Grove, NJ 

From White Plains: 1 hour 45 minutes

Those seeking a tranquil respite on the Atlantic should set their GPSs for this quaint coastal community. The spacious, uncommercialized boardwalk overlooking Ocean Grove’s immaculate white-sand beaches features a fishing pier for novice and experienced anglers alike, while shops and restaurants housed in charming Victorian buildings are just steps away. 

Delaware Water Gap, NJ & PA 

From White Plains: 1 hour 30 minutes

Talk about a never-ending photo op. This stretch of the Delaware River cuts through the Appalachian Mountains, dividing Pennsylvania and New Jersey. The land on both sides comprises the Delaware Water Gap National Recreation Area, offering myriad scenic drives, hikes, and picnicking, as well as year-round sporting opportunities.

North Fork Long Island, NY 

From White Plains: 2 hours

New York has come to produce some really respectable – and tasty – wines. The closest place to taste some of the state’s finest vintages is along Long Island’s North Fork at can’t-miss vineyards like Bedell, Shinn Estate, and Paumanok

Beacon, NY 

From White Plains: 1 hour

Brick-laced Beacon has a lot going for it these days, thanks to the shops and galleries that have sprung up in the wake of Dia:Beacon’s opening. But the best part is arguably the dining — most of which is right on Main Street. Don’t miss Kitchen Sink (left) for globally inspired eats, Ella’s Bellas bakery, Beacon Pantry for gourmet goods, and Denning’s Point for whiskey.  

Asbury Park, NJ 

From White Plains: 1 hour 40 minutes

This stretch of Jersey shoreline has pretty much everything you could want: a beachfront boardwalk; a cool dining scene; and The Market at Asbury Park, a collective of shops, artisans, and designers. Oh, and there’s also the Silverball Museum, where you can play pinball machines dating back to the 1950s. 

New Haven, CT 

From White Plains: 1 hour

Let’s make a case for New Haven: The Yale University Art Gallery is home to more than 200,000 items, including works by Rubens, Degas, and John Singer Sargent (left), to name a few. New Haven-style pizza, both traditional and modern, is the city’s claim to culinary fame. And every August, some of tennis’s biggest names descend on Yale for the Connecticut Open.

Cold Spring, NY 

From White Plains: 45 minutes

Known as a Metro-North stop with easy access to Breakneck Ridge hiking (once it reopens next year), this quaint town is also prime for eating and antiquing. Main Street’s boutique shops promise old-fashioned flair and artisan finds of all sorts, and no visit here is complete without a scoop (or three) at Moo Moo’s Creamery