8 Most Romantic Weekend Getaways from New York City

Food connoisseurs have long made the pilgrimage an hour north of Manhattan for chef Dan Barber’s highly praised farm-to-table dishes at Blue Hill at Stone Barns. But there’s more to the area than meets the review page. The neighboring hamlet of Pocantico Hills is home to Kykuit, John D. Rockefeller’s family estate, where you can stroll Beaux Arts-style gardens overlooking the Hudson River and see sculptures by the likes of Calder and Picasso. The art history lesson continues at the Union Church of Pocantico Hills (look for the stained-glass windows by Chagall and Matisse) or during a visit to the Edward Hopper House Museum and Study Center, in the artist’s former home in Nyack. The stylish Time Nyack makes an ideal base for exploring the charming shops on Main Street, but if you want to treat yourself to an evening worthy of an oil baron, Tarrytown’s luxurious Castle Hotel & Spa is just the place to do it.

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At the far eastern tip of Long Island, Montauk is the kind of laid-back beach town summer was made for. Booking a room at Gurney’s gets you access to the resort’s enviable private beach and spa, but don’t get too comfortable—warm-weather adventures await. Surfers and paddle boarders take to the waves at Ditch Plains, while bird watchers look skyward at Hither Hills State Park. For landlubbers with restless legs, your best bet is a sunrise hike that starts at the picturesque 18th-century Montauk Point Lighthouse—New York’s oldest lighthouse still in operation—and continues through sand dunes and sheltered forests along the Paumanok Path. Reward all that exertion with a lobster roll and glass of rosé on the waterfront patio at Duryea’s or, perhaps, dancing under the twinkle lights at trendy Surf Lodge.

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It’s no wonder artists flocked to this quintessential New England town in the late 19th century: the light is unlike anywhere else in the country. Get the full effect during an afternoon ramble along the Cliff Walk, an oceanfront path that ventures near the Gilded Age summer cottages of America’s wealthiest families including The Breakers, an Italian Renaissance mansion, and the Beaux Arts-style Marble House—both owned by the Vanderbilts. Farther inland, Chateau Sur Mer is a Victorian manse that’s just a leisurely stroll away from the quirky shops on Thames Street. Join the lively lunch crowd for chowder and fresh oysters at Bannister’s Wharf, or ditch the tourists and retreat to the dockside lounge at 41 North for a sundowner with a harbor view. Later, dine on local lobster and Point Judith calamari by candlelight at the 17th-century White Horse Tavern.

With its colorful Victorian homes and all-American charm, Cape May feels like a journey back in time. Close your eyes and you can almost hear the ragtime music playing in the antiques-laden rooms of the Stick-style Emlen Physick Estate, or the historic corridors of Congress Hall, the country’s oldest seaside resort. Other timeless diversions include hiking the wooded trails and dunes of Cape May Point State Park, where you can see all manner of wildlife from dolphins and whales off the shore to otters and migrating birds and butterflies, as well as the town’s famed lighthouse. Plant your umbrella at Cove Beach, which has been dubbed the king of Cape May’s coasts. If the heat gets the better of you, a drink on the veranda of the Virginia Hotel is sure to revive you.

For an understated alternative to the spectacle that overtakes the Hamptons each weekend, in-the-know New Yorkers board the ferry to Shelter Island, a tranquil spit of land along in the Peconic River sandwiched between Long Island's North and South Forks. Drop your bags at The Chequit, a refurbished 1872 hotel with pastel-hued rooms that serve as a quiet backdrop to your romantic getaway. Rent a bike and grab a takeaway lunch at local favorite Marie Eiffel Market before exploring the island’s shingled manor houses and untouched beaches. More ambitious types might choose to hike through the tidal creeks, freshwater marshes, and oak forests of Mashomack Reserve, or ply the calm seas by kayak or sailing class. Come evening, the place to be is on the upper deck of Sunset Beach’s Mediterranean restaurant—especially at twilight.

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Annapolis is often overshadowed by Baltimore, its neighbor to the north, but this postcard-perfect port town is a worth a visit in its own right. See its famous 18th-century architecture at places like the Palladian-inspired Hammond-Harwood House, built during colonial times, as well as the William Paca House & Garden, a 1760s Georgian mansion owned by a signer of the Declaration of Independence. From there, it’s a short walk to the Maryland State House, with its impressive dome, and the Beaux Arts grounds of the sprawling riverfront U.S. Naval Academy. Once you’ve dropped your bags at the stylish Loews Annapolis, make a beeline for City Dock to enjoy drinks and crab cakes on the sailboat-studded Chesapeake, then turn up Main Street for a sweet scoop at the Annapolis Ice Cream Co. (Their 36 homemade flavors are rotated daily, so multiple visits are encouraged.)

It’s worth the scenic three-and-a-half-hour Amtrak ride up the Hudson River to Saratoga, famous for its storied racetrack and iconic mineral springs. (JS Tip: Sit on the left side for the best view.) Bed down at Brentwood Hotel, a revamped 12-room motor lodge in Saratoga Springs that feels like a Brooklyn transplant thanks to its moody walls, brass fixtures, and Instagram-worthy bar. In the morning, drive 30 minutes north and rent a boat to explore the pristine shores of Lake George, the onetime summer playground of elite New York families like the Roosevelts and the Whitneys. The deckhands will help you tie up on the dock at The Algonquin, where you can enjoy a lunch of fish tacos and a shrimp-garnished Bloody Mary. Then make your way to The Sagamore, a white clapboard Gilded Age hotel that occupies its own island nearby.

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Northeastern Pennsylvania’s Pocono Mountains are a popular winter destination for Mid-Atlantic skiers, but the year’s other months prove even more inspiring for a romantic rendezvous. Just 90 miles from New York, nestled within 150 acres of unspoiled woodlands, the adults-only Lodge at Woodloch is a perfect perch from which to take in the region’s natural splendor. The resort can arrange everything from kayaking on a 15-acre private lake to horseback riding along the forest trails. If that’s more action than you crave, unwind in the heated hydromassage pool at the 40,000-square-foot spa or choose between yoga and tai chi classes, then head over to the restaurant to feast on seasonal farm-to table meals made with ingredients sourced from the on-site garden.