Have the elaborate winter igloos and cozy bungalow-style dining settings flooded your social media feeds yet? How about ones with views of snow-dusted vineyards, sugar-frosted fields, and shimmering waterfronts?

While there isn’t a bad time to visit Long Island’s award-winning wine region known as the North Fork, the off-season – after the wave of pumpkin-pickers has receded - is arguably the most ideal time to visit.

As the cold weather moves in, many businesses roll out the white carpet for guests with unparalleled, cozy settings, exclusive seasonal tastings, and a slate of live entertainment and activities. And with slimmed down crowds adding to the serenity and an affordable winter edge, there’s no better time to tuck in and taste the terroir of Long Island’s North Fork.

So, whether you’re looking for a picturesque winter weekend getaway with the girls, or you’re a true wine aficionado looking to cozy-up with a lively red, you’ll want to check out these wonderous winter winery experiences on Long Island.

RGNY (Riverhead)


Visit RGNY in style this winter with their intimate Greenhouse Experience. Offering a unique setting for 2-6 guests, each of the four greenhouses have Mexican-inspired décor, paying tribute to the vineyard’s founders, sweeping views of the property, and come equipped with an adjustable heater and speakers. Curl up on the couches, choose your favorite wine, and enjoy a delicious lunch and dessert combo in a private, picturesque greenhouse – sure to be the envy of your Instagram followers.

OVERNIGHT STAY OPTION:  Make it a weekend getaway by taking advantage of the MTA Away Deal to Hotel Indigo Long Island - East End, or stay at The Preston House or Jedediah Hawkins Inn.

Macari Vineyards (Mattituck)

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Macari Vineyards offers three immersive, and truly unique settings for an unrivaled winter wine tasting experience. Guests can unwind and escape the winter chill in Macari Vineyards’ Winter Lodge, a cozy and inviting intimate tasting suite that has been reimagined with a ski-lodge-inspired design and charming alpine-style décor.    

Or experience the warmth and luxury of their Bergen Road Bungalows. Designed with a wine lounge-inspired aesthetic, these heated outdoor tents provide an elevated and intimate setting for guests to disconnect from the outside world and reconnect with nature among world-class wines, gourmet bites, family, and friends. Nestled vine-side, each tent can accommodate up to eight guests and features a tented dining room where you can sit down to a sumptuous spread of mezze pairings prepared by Chef Lauren Lombardi.

Guests can also enjoy top-rated Macari wines in their wood-beamed working Barrel Cellar for a more classic and cozy setting. 

OVERNIGHT STAY OPTION:  Make it a weekend getaway by staying at the Cedar House on Sound B&B (Mattituck), Aqua by American Beech, or the Shoals (close to Mattituck). 

Wölffer Estate (Sagaponack)

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Open year-round, seven days a week, the tasting room at Wölffer Estate is both a center of activity and place of tranquility. Guests are warmly welcomed into a rustic-modern space perched on a rise overlooking the lush vineyards and gently rolling Hamptons landscape.  Wölffer’s Candlelight Fridays in their Tasting Room are not to be missed.  The weekly event features live music from local musicians and a refreshed menu with seasonal pairings, new wine and cider release, and more on Fridays in January at 5:00 p.m.

OVERNIGHT STAY OPTION:  Make it a weekend getaway by staying at the Topping Rose House or Southampton Inn.

Lieb Cellars (Cutchogue)

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Lieb Cellars owns the largest contiguous plot of Pinot Blanc in the United States and is known for their signature dry, clean and fruit-forward style. Located in Cutchogue under the guiding hand of veteran winemaker Russel Hearn, the 35-year-old vines have produced nationally recognized and award-winning wines. Lieb Cellars has a Friday night music series every Friday from 5:00 p.m. to 7:00 p.m. until March. Listen to live music in the tasting room and enjoy wine by the glass or bottle in addition to their food menu. And, check out their sister property, Bridge Lane in Mattituck, offering a slate of unique events from Tarot Card readings to Mixology classes.

OVERNIGHT STAY OPTION:  Make it a weekend getaway by staying at the the ShoalsAmerican Beech or the Sound View.

Sannino Vineyard (Cutchogue)  

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The North Fork features more than 60 wineries, some of which provide one-of-a-kind, charming accommodations right on the property where you can enjoy life as a vintner for a night, a weekend, or longer. And Sannino Vineyards in Cutchogue is one of those properties. Not only does the family-owned vineyard provide a Tuscan styled on-site B&B with stunning views of the main estate and vineyards, but you can take your vintner fantasies to the next level with their VIP Blending Session-Wine Making Experience.

Following a full tour of the property, Anthony Sannino provides a true winemaking experience, guiding participants in blending their own custom wine that they can take home. This event is just one of the series of events happening throughout the winter including their Mini Cupcake & Wine Pairing series, Pizza & Mimosas Sunday brunch series and more. 

OVERNIGHT STAY OPTION:  Make it a weekend getaway by staying at the Sannino Vineyard B&B.

Harmony Vineyards (Head of the Harbor)

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The harbor-side vineyard is open year-round so you can walk the grounds and then step inside the historic 1690 home to enjoy some wine at the bar while the fireplace crackles. Reserve an igloo at Harmony Vineyards, come to Friday night trivia, check out the Speak Easy Party in January or the chocolate and wine pairing in February. 

OVERNIGHT STAY OPTION:  Make it a weekend getaway by staying at the Three Village Inn (Stony Brook).

Ospreys Dominion (Peconic)

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With ninety acres of vinifera grapes growing under the watchful eye of the soaring Osprey, the vineyard’s namesake, Ospreys Dominion in Peconic is open year-round with live music from 1:00 p.m. to 4:00 p.m. on Saturdays starting January 21. Enjoy mugs of their “Winter Classic” spice wine by the fire pit on their patio seven days a week from 11:00 a.m. to 5:00 p.m.

OVERNIGHT STAY OPTION:  Make it a weekend getaway by staying at the ShoalsAmerican Beech, Menhaden, or the Sound View.

Pindar Vineyards (Peconic)

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A North Fork staple and one of the region’s oldest vineyards, Pindar Vineyards is hosting live music in their tasting room in January from 1:00 p.m. to 5:00 p.m. starting January 21 on select weekends. Encompassing more than 500 scenic acres, growing 17 varieties of grapes, and crafting them into 23 varietal and proprietary blends, Pindar Vineyards produces 70,000 cases of wine a year.

Enjoy handmade pieces of fudge from Chocology Unlimited in Stony Brook, matched perfectly with Pindar wine at the Chocology Fudge Pairing at the vineyard along with a Winter Paint and Sip night where guests can paint two wine glasses in January. Put your hands together at the Pindar Vineyards Comedy Night also in January, with a lineup whose credits include top festivals, TV, and major club appearances. 

OVERNIGHT STAY OPTION:  Make it a weekend getaway by staying at  the ShoalsAmerican Beech, Menhaden or the Sound View.

Raphael (Peconic)

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Built, owned, and operated by four generations of family, Raphael is a premier North Fork boutique vineyard located on 70-acres of grounds inspired by Mediterranean architecture. Raphael Wine offers exclusive cellar tastings that include access to their library wines, personalized wine tastings and charcuterie plates, as well as wine education and conversation. The winery also hosts complimentary live music every Saturday and Sunday in their tasting room as part of Raphael’s North Fork Cabin Fever Series.

OVERNIGHT STAY OPTION:  Make it a weekend getaway by staying at the Shoals, MenhadenAmerican Beech or the Sound View.

Rose Hill Vineyards (Mattituck)

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A bucket list experience, Rose Hill is a vineyard and bed & breakfast located in the heart of the North Fork, tucked away on Oregon Road.  Stay the night at the beautifully restored, historic farmhouse inn for a natural hideaway for relaxation and indulgence or visit cozy wine library with barrel cellar views for an intimate and memorable afternoon.  

OVERNIGHT STAY OPTION:  Make it a weekend getaway by staying at the Rose Hill Vineyards B&B. 

Bedell Cellars (Cutchogue)


A pioneering family-owned winery, Bedell Cellars hand crafts their wines in small batches with a commitment to sustainable farming. Experience the intimacy of their loft area this winter with its vaulted ceilings and fireplace and viewing windows into the barrel aging cellar.

OVERNIGHT STAY OPTION:  Make it a weekend getaway by staying at the the ShoalsAmerican Beech, or the Sound View.

Lenz Winery (Peconic)

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Lenz Winery, one of the founding vineyards on the North Fork, has embraced newer trends with food trucks, live music, Cozy Up Igloos and fireside tastings, while preserving the farm’s historic and bucolic setting that visitors love. Visit the tasting room this winter to experience an indoor table-top firepit and their “sip & s’more” or checkout their variety of events throughout the year from barrel tastings with the winemaker, vineyard tours and library tastings. Other activities include the Merlot Classic, Dinner in the Vines, and more.

OVERNIGHT STAY OPTION:  Make it a weekend getaway by staying at  the Shoals, MenhadenAmerican Beech or the Sound View.