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Trip Ideas

How to Do Long Island in Off-Season

With summer 2016 now long gone (RIP), it may seem like Long Island's prime vacay stretch has also kicked the seasonal bucket. But hear me out – because far from closing up shop, it's in autumn that LI's weekender crowds disperse, hotels see major price dips, and brisk walks along super-soft beaches are at their utmost romantic. Here, JS correspondent Chelsea Stuart does us a solid, going in search of the best places to eat, drink and play this off-season.

A Brooklyn-based writer and editor, Chelsea's work has appeared in Matador Network, The Huffington Post, the TripAdvisor blog, and more. When not planning her next trip, you'll usually find her drinking way too much iced coffee (always iced—she’s from New England) or bingeing a Netflix original series.

See recent posts by Chelsea Stuart

Prior to a recent four-day trip through Long Island, my knowledge of LI was embarrassingly (read: staggeringly) limited. In my case, this meant I had a grasp on only basic geography, the pure existence of Stony Brook University, and what I could piece together from Kourtney & Khloé Take The Hamptons (aka a high-concentration of oceanside mega-mansions, celebs with too much time and money, and swan pool floaties – lots of ’em).

But driving out of midtown Manhattan, through Queens and into Nassau county, I quickly realized what a tiny, incomplete picture of Long Island that truly was. Over a couple of days, I worked my way from Garden City (roughly an hour outside of NYC) to Montauk and back again. I stopped in countless historic hamlets and picturesque villages, uncovering a different side of Long Island – one full of lush vineyards, grandiose Gold Coast mansions, and charming storefronts, all set between rambling stretches of countryside. That said, here’s my cheat sheet to everything worth exploring.

Where to Stay

Gurney’s Montauk Resort & Seawater Spa, Montauk

One of Montauk’s only year-round resorts, Gurney’s is still fresh off of a major 2014 facelift which saw the complete renovation of 38 oceanfront rooms. Despite chic industrial-meets-beachy rooms and a prime bluff-side locale overlooking a 1,000-foot private Hamptons beach, the resort’s main siren call is its seawater spa. The massive complex marries an ocean-fed seawater pool framed by floor-to-ceiling windows; a Finnish-style rock sauna that pumps out rejuvenating dry heat; a eucalyptus-infused Russian steam room heated to 120 degrees; a Roman bath; and a Swiss shower.

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Danfords Hotel & Marina, Port Jefferson

Many people assume Long Island vacations can’t be done without a car but many people are wrong. If you plan it right, it’s totally doable. For starters, local visitors – like those on the other side of the sound, in Bridgeport, CT – can hop a ferry to historic Port Jefferson. Mere steps from PJ’s terminus is Danfords Hotel & Marina where spacious, nautically-styled rooms and suites overlook the shops of the village’s downtown and the Long Island Sound.

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Courtesy of Elliot Kaufman Photography

Oheka Castle, Huntington

If you’ve been dreaming of living through the Roaring Twenties or attending a Gold Coast mansion party since your required reading of The Great Gatsby in middle school, then this is your chance to realize said fantasy. The opulent, French Chateau-style Oheka Castle is the second largest private residence in the US (behind North Carolina’s Biltmore Estate), and speaks to a dreamily decadent time gone by. The stately quarters are also rich in history, having originally been the personal home of a German Wall Street tycoon, and then serving stints as a retirement home for NYC sanitation workers (yes, really), a training school for Merchant Marine radio operators, a military academy, and most recently, the venue for Kevin Jonas’s wedding and Taylor Swift’s "Blank Space" music video. No two rooms are alike, but in each of the 32 sophisticated guestrooms and suites you’ll find some variation of ornate chandeliers, 100 percent Italian Egyptian cotton linens, clawfoot baths and jetted soaking tubs, and Molton Brown amenities.

RELATED: The World’s Best Castle Hotels

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Baron’s Cove, Sag Harbor

If it’s good enough for Jackson Pollock, John Steinbeck, Truman Capote, and Kurt Vonnegut, then it’s sure as hell good enough for us. This 1960’s mainstay just reopened in 2015, following a two-year top-to-bottom revamp which elevated its existing layout with the addition of a new pool, restaurant and bar. Just a few minute’s walk from the charming storefronts of Sag Harbor’s main street, the all-season resort charms with tastefully All-American, nautical interiors – namely, pineapple wallpaper, pompom fringed curtains, old-timey maps, Ralph Lauren fixtures, and baby blue accents – a heated saltwater pool, and complimentary cruisers (with wicker baskets) for riding along the marina. For those traveling without a car – the local Jitney bus stops just down the street, or you can arrange for a hotel pickup from the Bridgehampton train station.

See All Long Island Hotels

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Where to Eat and Drink

MP Taverna, Roslyn

Long Island may not have the culinary prestige of its western neighbor – NYC – but chef and restauranteur Michael Psilakis is confident that the area has what it takes to sustain gourmet spots all the same. As the owner of five restaurants – including two on the Upper West Side – a co-star on BBC America’s No Kitchen Required, and contestant on Cutthroat Kitchen and Iron Chef America, we’re keen to believe him. At MP Taverna, Roslyn, his modern Greek brasserie, Psilakis serves up mezes like barrel aged feta and Cypriot lamb sausage alongside entrees of grilled swordfish and spicy paella – all inspired by the distinct flavors and traditional dishes of his childhood.

Love Lane Kitchen, Mattituck

If the Gilmore Girls took place on Long Island, we just know they’d be spending ample time dining and shopping on Mattituck village’s Love Lane. There’s a rustic market, sweets shoppe, village cheese shop, boutique clothing store and tiny US Post Office, and if that doesn’t paint a quaint enough picture, the North Shore hamlet even hosts an annual Old Fashioned Street Fair (with adorable Little Miss Mattituck and Little Mr. Mattituck competitions). One enchanting anchor on the block is Love Lane Kitchen. The hole-in-the-wall eatery radiates what owner Carolyn Iannone calls a “living room feel” while weekly dinner menus with options like free range, local apple cider and herb-marinated chicken, and pear and red swiss chard salad, revolve around seasonal, locally-sourced ingredients.

Jerry & The Mermaid, Riverhead

Locally-caught sustainable seafood (done every which way) is a family affair at Jerry & The Mermaid – a popular Riverhead spot that’s run by father-son duo Jerry and Jerry Jr. Between the lunch and dinner menu, you’ll find options like Peconic Bay scallops over linguine, grilled Mako shark with roasted peppers, panko breaded flounder sandwiches, and pignoli nut crusted grouper. While the restaurant’s indoor dining room and bar, and comfortable outdoor patio that looks out on the Treasure Cove Resort Marina have an unmistakably casual atmosphere, just ask Jerry Sr. about special guests (he’s known to check in on tables) and he’ll tell you about the time Lady Gaga visited.

Pindar Vineyards, Peconic

If you’re familiar with the North Fork in even the slightest, then you’re probably keyed into the wine scene. If not, let us tell you – the East End wine country is home to more than 30 vineyards, and this fall, Pindar is one of our top picks thanks to weekends full of live music and champagne tours come October and November. No matter when you visit, stop by the tasting room to sample some of our favorite varietals (there are 23 in total), like Sunflower Chardonnay, Cabernet Port and Dessert Riesling, before retiring to the back deck with your glass of choice, where you can look out on 500 verdant acres of vineyard, lush with 17 different types of grapes.

RELATED: Why the North Fork Should Be Your Next Getaway

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What to Do

Fire Island Lighthouse, Fire Island

A quick flight of 182 spiral steps separate you from the ground and panoramic views of Robert Moses State Park, the Great South Bay, and on a clear day, the NYC skyline. The iconic South Shore structure was first constructed in 1825, before going through a number of restorations and paint jobs, eventually acquiring its identifying black and white bands in 1891.

The Jazz Loft Museum, Stony Brook

May 2016 was an exciting time for Stony Brook, as the idyllic village finally debuted its new jazz museum, performance space and educational center, as made possible by a crowd-sourced half-a-million-dollar renovation of the former Suffolk Museum (and before that, town fire house). Today, the nonprofit functions as a showroom for musician and historian Tom Manuel’s personal collection, with memorabilia from some of the greatest jazz performers ever known – including Miles Davis and Milt Hinton – as well as a busy venue, with a bandstand constructed from flooring salvaged from New York’s Roseland Ballroom. Plan your visit wisely as you can Lindy Hop the first Saturday of every month with Swing Dance Long Island; attend all-age jam sessions on Wednesdays; and check out everything from big bands to soloists, and orchestras to pre-college program performances on Thursdays and Fridays.

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Sagamore Hill National Historic Site, Cove Neck

History buffs will want to make a stop in Cove Neck to check out Sagamore Hill, Teddy Roosevelt’s personal estate. While the 26th president of the US was a born and raised Manhattanite, he grew fond of the Oyster Bay area after vacationing there as a child. When he graduated college and got married, he decided to officially settle down there, building a 23-room Queen Anne-style Victorian home where he was to live from 1885 until his death in 1919. Today, visitors can peruse “The Summer White House” (he spent seven summers in office there) on daily tours that take you through his library with its 6,000 or so books (only half of his original collection) and the North Room, a massive man cave, of sorts, filled with paintings, sculptures, gifts from foreign dignitaries, and his prized game trophies.

Oyster Bay Brewing Company, Oyster Bay

Ask anyone with a little know-how, and they’ll confirm that craft beer is treat to be enjoyed year-round. But just as latte fiends anticipate fall’s bestowal of the PSL on Starbucks’ seasonal menu, pumpkin beer fanatics start their own countdowns each year. At the Oyster Bay Brewing Company, the time is right, so you can go all in sipping pints of Pumpkin Ale, or enjoying full flights of handcrafted varieties like Grapefruit IPA, Sagamore Dark Lager, Baymen’s Oyster Stout, and Honey Ale (made will local honey from Locust Valley’s Bee Haven).

RELATED: The Best Beer Gardens in the U.S.

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The Culper Spy Ring, East Setauket

If you’ve been following AMC’s TURN: Washington’s Spies, then you already know a bit about this, but if not – listen up. In the summer of 1778, George Washington called upon Benjamin Tallmadge – a cavalry officer from Setauket, LI – to form the covert Culper Spy Ring, the very first in the US. Along with other locals like Abraham Woodhull, Robert Townsend, and Caleb Brewster, Tallmadge was tasked with gathering intelligence on British troops occupying Long Island and NYC. Using invisible ink, coded words and a system of signals and couriers, the group relayed information straight to Washington through the end of the war in 1783. Today, visitors to the North Shore can travel the heritage trail, stopping at spots like the Brewster House and Strongs Neck (where Woodhull resided).

Harbes Family Farm Stand, Mattituck

Pumpkin patches, apple orchards, corn mazes, oh my. Thirteen generations of North Fork Harbes have transformed a once husband-and-wife corn stand into multiple family farms, a vineyard and orchard across Mattituck, Riverhead and Jamesport. This autumn, the farm isn’t playing – ok, technically they are – with Wizard of Oz-, Snoopy-, Robin Hood-, and Giant Pumpkin-themed mazes, and on-the-vine pumpkin patches galore. During you visit you can also stock up on farm favorites like apple cider donuts, caramel and candy apples, and handcrafted wines which beg to be tried out first in the wine tasting barn.

Moku Loa Paddle Tribe, Oakdale

If you’ve never paddle boarded before, take it from us – you’ll likely shake like a leaf for the first few minutes. But once your adrenaline is pumping and you get in the swing of things, cruising gently over calm waters is just about one of the most relaxing things we can think of. Whether you’re looking for a first-time lesson, a rental, or a group to paddle with, the Moku Loa Paddle Tribe is your LI-based answer. Every Wednesday at the Oakdale Yacht Club, the tribe’s fleet takes off for a sunset paddle along the Connetquot River.

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Photo courtesy of Laura Verdino

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