Five Essential Day Trips from New York

Five essential day trips from New York

Where do you go when a New York minute is too long? Most travellers don’t look beyond the bright lights of the big city. But not far from the island of Manhattan, five small towns offer culinary delights, seaside pleasures and enough art and culture to rival even New York’s most famous museums and restaurants. Escape the concrete jungle with these essential day trips within convenient distance of the city.

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1. New Canaan, CT

Experience New England just moments from the New York border. Connecticut’s Instagram-worthy towns and incredible farm-to-table restaurants make it a worthy destination in its own right. But for a quick day trip, take the Metro-North commuter rail to New Canaan, where acclaimed architect Philip Johnson built The Glass House in 1949. Designed in the International Style, the 55-foot-long home was the private residence of the architect, known for designing famous Manhattan skyscrapers like the Seagram building as well as the Lincoln Center complex.

The Glass House New Cananaan

The Glass House | Photo: Michael Biondo

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Main Street is decorated with patriotic American flag banners, due in part to Oyster Bay being where president Theodore Roosevelt and his wife raised their family in the early 1900s

2. Oyster Bay, Long Island, NY

Why make the 100-mile-long journey to the Hamptons when you can get to Oyster Bay in less than half the time? Step from the Long Island Railroad platform into the town’s waterfront park or take a minute-long walk into town. Main Street is decorated with patriotic American flag banners, due in part to Oyster Bay being where president Theodore Roosevelt and his wife raised their family in the early 1900s. Sagamore Hill, their 23-room Victorian home, is now a National Historic Site with guided tours.

While the Roosevelts once gave the town distinction, Oyster Bay became a sleepy hamlet in the second half of the 20th century. Now it’s coming back to life, thanks to local celebrity Billy Joel who put his vintage motorcycle collection on display at 20th Century Cycles. Across the street at 2 Spring, Iron Chef America winner Jesse Schenker serves brunch with a costal flourish. Go for the tangy Bloody Mary and stay for dishes like eggs Benedict with fresh Maine lobster poached in butter.

3. Fair Harbor, Fire Island, NY

Federally-protected, far-flung Fire Island isn’t as removed from the city as the map makes it appear. The island is accessible only by ferry and is mostly free of cars, which creates a feeling that you’re a world away from civilization. While party-friendly Ocean Beach Village and the gay enclaves Cherry Grove and Fire Island Pines are wildly popular, opt for a laid-back beach day in quaint and quiet Fair Harbor.

There are no streets or sidewalks in Fair Harbor. The main street is a sandy path that bisects a network of boardwalks, which connect tiny, century-old beach houses to the ferry stop on the north side of the island and the Atlantic Ocean on the south shore. Locals walk around barefoot, except to Le Dock, a Jean-Georges restaurant where you can enjoy fresh local seafood during your relaxing day at the secluded beach.

Sound View Greenport Long Island

Sound View | Photo: Read McKendree

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4. Beacon, NY

Since Dia:Beacon opened in 2003, New Yorkers have taken trains in droves to the outstanding contemporary art museum on the banks of the Hudson River. While Dia: Beacon has been the main draw, there’s plenty more to see and do. Mount Beacon, the tallest summit in the Hudson Valley, offers one of the region’s best hikes. Cosy coffee shops and cafes line Main Street, while The Roundhouse restaurant in a converted factory with floor-to-ceiling windows looking out over Beacon Falls is not to be missed.

The Roundhouse Beacon New York

The Roundhouse Beacon | Photo: Eric Laignel

The Roundhouse Beacon New York

The Roundhouse Beacon | Photo: John Bellenis

5. Greenport, Long Island, NY

Voted one of the prettiest towns in America, Greenport is packed with local charm. Founded on the bucolic North Fork of Long Island in 1838, the town is known for its oysters, wineries and all the beautiful water views you could hope for. There are dozens of vineyards and wineries in the area, but Kontokosta has one of the best tasting rooms set on a bluff overlooking the Long Island Sound. For the freshest seafood, long-time establishments like Claudio’s can’t be beaten.

Turn a day trip into a weekend getaway at Sound View Greenport, a 1950s motel that was transformed into a contemporary hotel by Brooklyn-based design firm Studio Tack. Located directly on the water, the hotel is complete with farm-to-table dining at The Halyard restaurant and live music at the Piano Bar. A stay here will make you feel less like you’re near the water and more like you’re in it, especially with picture windows in the rooms and al fresco dining with unparalleled views.

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