16 Great Day Trips

Come out of winter-hibernation mode, hop in the car, and take a staycation to one of our favorite destinations.


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With a breathtaking view of Stockbridge Bowl (aka Lake Mahkeenac), Olivia's Overlook is a great scenic pitstop to make while visiting Stockbridge, MA.

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Quick Picks

Asbury Park 

Driving time from Poughkeepsie: 2 hours, 20 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 Windsor 

Driving time from Poughkeepsie: 40 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.

 

Westhampton 

Driving time from Poughkeepsie: 3 hours
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

 

Warwick 

Driving time from Poughkeepsie: 1 hour, 10 minutes
Warwick's 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.  And in the fall, it's one of the best places in the state to go apple-picking.

 

Nyack 

Driving time from Poughkeepsie: 1 hour
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.

 

Beacon 

Driving time from Poughkeepsie: 30 minutes
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 (above) for globally inspired eats, Ella’s Bellas bakery, Beacon Pantry for gourmet goods, and Denning’s Point for whiskey.

 

Ocean Grove 

Driving time from Poughkeepsie: 2 hours, 30 minutes
Those seeking a tranquil respite on the Atlantic should set their GPSs for this quaint New Jersey 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. 

 

Cold Spring 

Driving time from Poughkeepsie: 40 minutes
Known as a Metro-North stop with easy access to Breakneck Ridge hiking, 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

 

North Fork 

Driving time from Poughkeepsie: 3 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, with can’t-miss vineyards like Bedell, Shinn Estate, and Paumanok

 

New Haven 

Driving time from Poughkeepsie: 1 hour, 45 minutes
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 (above), 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.

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