10 Reasons To Make a Long Island Escape This Season

Nov 6, 2018

Though best known as a summer hotspot (see: celebrity-studded beach towns), Long Island is equally beloved among insiders for its year-round draws—from award-winning wineries to century-spanning historic sights to jaw-dropping vistas, all blessedly crowd-free in the "off-season." That is, now. 

Beyond the increased elbow room and accordingly reduced room rates, you'll find that pretty much everything you want to do is easily accessible. Whether you're driving in from New York City, taking the Long Island Railroad from Penn Station, ferrying in from Connecticut or flying into Long Island MacArthur Airport (or La Guardia or JFK) from the rest of the world, check out this travel info hub to plot your course—then consider hitting any number of our favorite stops:


Hugging Long Island Sound, the North Shore is the Gold Coast of famed Gatsby-era mansions. Drive and gawk your way past a number of them—or make yourself at home: You can actually book a stay at OHEKA Castle, one-time country home to financier Otto Hermann Kahn, whose digs you may recognize from Citizen Kane or Taylor Swift's Blank Space video, among others. 

Perhaps not surprisingly for a Gilded Era getaway, this town is also a hub of arts and culture. Check out the Heckscher Museum of Art, where mid-November ushers in Rivera and Beyond: Latin American Art from the Joan and Milton Bagley Collection, an astounding who's who that includes, among others, Colombia's Fernando Botero, Cuba's Wilfredo Lam and Mexico's Elena Climent. 

For performing arts, head to the Paramount, where the next few months will see performances by everyone from Kansas to Ken Jeong (of Crazy Rich Asians fame).

Stony Brook

Another arts enclave worth stopping in: Stony Brook, home to everything from the Jazz Loft—where you'll find hundreds of instruments, diaries and sheet music from jazz greats—to the Long Island Museum of American Art, History and Carriages. Informally known as the Long Island Museum, this Smithsonian affiliate houses a collection of more than 100 horse-drawn carriages from as far back as the 1700s.

While you're in the neighborhood, check out The St. James General Store. Opened in 1857, this retail time capsule is a must-visit for everything from molasses candy to pottery, plus weekend visits from Santa in December.

Along Route 25A, keep an eye out for Washington's Spy Trail signs, a reference to GW's secret agents during the British occupation of Long Island. (The AMC series Turn makes for an entertaining primer on the subject.) And for the full effect, stay at the Three Village Inn, where the cottage houses are named after Washington’s local spies.

Port Jefferson

Port Jefferson is home to some of the most gasp-inducing views on the island. To pair them with an equally memorable meal, head to Wave Seafood & Steak in Danford's Hotel and Marina, where your harbor vistas come with one of the Island's most epic Sunday brunches. And if you're there for lunch, don't miss the fish & chips.

Views aside, going Down Port (as it's known to locals) offers all manner of wintertime fun, from ice skating (November through March) to the annual Dickens Festival (Dec. 1 and 2), complete with costumed characters from "a Christmas Carol" and decorated streets.


The Island's North Fork—famed for farms, fields and vineyards—is home to Mattituck, a vinophile favorite, with 30+ wineries for your consideration. But if you're there on the weekend and you've got the kiddos in tow, go straight to the Harbes Family Farm and vineyard. While the designated driver (and parent) ushers the family through the farm animal feeding areas, the hedge maze and perhaps a musical hayride, the other grownup can taste the award-winning varietals at the resident wine barn, home to the North Fork's first certified sustainable wines. As to who's having more fun, we'll leave that call to you.

For more substantial fueling up, head to Love Lane Kitchen (conveniently, on Love Lane)—a seasonally-driven local favorite where each meal service rivals the last. Word to the wise: Whatever the seasonal breakfast pancake, go for it—unless you're more of a pastrami hash person, in which case, don't miss this house-made version. 

Of course, you won't need to go more than a few feet for breakfast if you book at stay at the Shinn Estate Vineyards Bed & Breakfast—a restored farmhouse on a 22-acre vineyard where you'll start the day with the likes of organic quiche, house-made granola and scones and local breads and yogurts. To say nothing of the complimentary wine tastings.


Wine isn't all that's on tap here; Long Island's craft breweries have gained a huge following of their own lately. To see why, visit the tasting room at the Greenport Harbor Brewing Company, where seasonal brews include the pumpkin-y Leaf Pile Ale and malt-forward Anti-Freeze Ale—and often come with performances by local bands.

While you're in town, see why chef Noah Schwartz—of Noah’s fame—has been called out by everyone from the New York Times Travel section to the James Beard Foundation. Between his creative take on locally sourced seasonal ingredients and his wife Sunita's estimable wine wisdom, meals here are the very picture of destination dining. And if Crescent Farm Duck BBQ is in the house when you are, don't miss this taste of the famed Long Island Duck.

To ensure that you'll have at least a brief opportunity to walk off dinner, stay at the cozy Ruby’s Cove bed and breakfast (a five-minute stroll away). On the other hand, if you like to just collapse in bed after a good meal, know that the amenity-packed and view-blessed Harbor Front Inn is more or less 150 feet away.

Sag Harbor

A centuries-old fishing and whaling village, this South Fork favorite is worth a stop for the quaintness quotient alone. But if your tastes lean at all literary, you'll want dive deeper into this writer's haven, former home to everyone from James Fenimore Cooper to John Steinbeck to Betty Friedan.

Key stops on the arts and letters circuit include the acclaimed Bay Street Theater, whose productions often wind up on and off Broadway (up next: The Great Gatsby)—and cult favorite Canio's Books, home to readings, workshops and film screenings. Note to Melville fans: You may want to mark your 2019 calendar. Canio's stages an annual Moby Dick Marathon weekend each June, but given that next year is the 200th anniversary of the author's birth, lit's gonna get crazy. 

In keeping with the baleen theme, don't miss the Sag Harbor Whaling & Historical Museum—an 19th century whaler's home turned National Register of Historic Places-listed collection of Ahab-worthy artifacts. And for total immersion, as it were, stay in another architectural holdover of the whaling era here: The American Hotel, built in 1846—and still appointed with period pieces (but with plenty of 21st-century amenities, too).


Time was, out-of-towners would visit the Montauk Point Lighthouse and go on their merry way. But the local hotel and restaurant scene has upped its game so dramatically of late, you're going to want to stay a while. Park your stuff at Hero Beach Club (home to nightly s'mores at the resident fire pits, whatever the season) or Gurney's Inn & Spa (where the thalassotherapy treatments alone are worth a stay). Then stop by the Montauk Brewing Company for a newly released Pumpkin Ale before sampling the sharable small plates—especially the MTK Chowder and mac & cheese with orzo, peas and bacon—at Swallow East.

Of course, the lighthouse—commissioned by George Washington in 1792 to sit as far east as one can go on the island—remains a huge lure (and sunset shots from the top remain Instagram gold). Just check here to make sure the building is open when you're in town (the schedule varies throughout the year).

East Hampton

Twenty or so hamlets and villages make up the star-studded Hamptons, but East Hampton is a celebrity in its own right, with destination dining (the Heavenly Biscuits at East Hampton Grill are legend); killer shopping (see Kirna Zabête or—for vintage designer finds—What Comes Around Goes Around) and A-List people watching.

Of course, East Hampton is more than a bastion of beach chic. For some local history, head to the Home Sweet Home Museum, one family's Colonial Revival retreat within 18th-century architectural bones. To carry that 1700's spirit into dinner, visit the aptly named 1770 House, purveyor of well-loved local seafood dishes (think sea scallop crudo with corn, truffle, cilantro and citrus)—and a repeat recipient of the Wine Spectator Award of Excellence.


To experience the South Shore's decidedly down-home side, head to Sayville, birthplace of the beloved Butera's. Though this is now a three-restaurant empire spanning the island, the original remains right here on Main Street, where the family-style Italian fare is dished out in famously generous portions. The chicken meatballs are perennial favorites, but you should also ask about the crispy grilled pizza of the day.

To walk off (a fraction of) the meal, stroll over to the Long Island Maritime Museum—a testament to the pre-electronic-navigation days of shipwrecks aplenty along the Island's barrier beaches. You'll find acres' worth of ill-fated 18th- and-19th-century vessels, or at least remnants thereof. For maritime spoils of a different kind, head over to Island Strong and shop this local favorite line for anchor- and lighthouse-adorned hoodies, caps or tees.

Fire Island

Fire Island, the most bohemian of Long Island's beach communities, is car-free, making the local nature especially pristine. After you've ferried or water-taxied over, check into a place with direct access to at least one natural element: the water, which you'll have nonstop views of from Ocean Beach's The Palms Hotel

Then make your way to Sailor's Haven, where you'll find a singular patch of wilderness: the Sunken Forest, a 300-year old holly forest which you can see from a boardwalk that takes you through freshwater bogs and dunes.

For a more expansive view of the local nature, head to the Fire Island Lighthouse—160 years old this year.  But the birthday isn't the only cause for celebration here: The 16th annual Reenactment of the Flying Santa takes place on Dec. 8, when Saint Nick does an airdrop of holiday gifts for the lighthouse keeper's clan, then stops by the lighthouse for photo ops.

On the other hand, pretty much any day's a celebration when you reach the top of these 192 stairs and take in the Atlantic panorama.

Ready to go? Visit DiscoverLongIsland.com for trip ideas, things to do and help planning a Long Island getaway.

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