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Holiday Sips and Sights Along the Shawangunk Wine Trail

Between the snowy fields, the Santa sightings and the fantastical light displays, the holiday season in the Hudson Valley sparkles all by itself. Add a glass or two of locally produced sparkling wine, and you’ll be ready to celebrate.

There are dozens of wineries in the Hudson Valley to visit, all of which will have their own array of holiday attractions, deals, décor, and special sips. But if you want a more specific itinerary, hit the wineries, cideries, and distilleries on the Shawangunk Wine Trail. Just 60 miles north of New York City, the Shawangunk Wine Trail rolls out the red carpet for the holidays. Plan a route and get your bliss on!

Wreath Fineries

One of the most popular holiday events in the state is the Shawangunk Wine Trail’s annual Wreath Fineries at the Wineries event. Get into the spirit by donning seasonal gear or your fugliest holiday sweater, and head out on a self-guided tour of tasting rooms decked out for the season with staff ready to pour delicious tastes of their best wines.

But if the Fineries event is sold out by the time you log on to snag a ticket, don’t worry. You can check out each winery, cidery, and distillery on your own and still get a bracing dose of holiday cheer. Sample these holiday-inspired drinks at the wineries yourself, then buy an extra bottle to put under the tree of your favorite local libation lover. Make it extra festive and hit one of the events!


Angry Orchard: Cidery Sips

This historic orchard has been growing apples for more than 100 years, and it takes celebration seriously. In the tasting room, savor their home-grown ciders and special offerings like Pommeau which feels especially festive this time of year. The barrel-aged, fortified apple cider is a blend of Eau de Vie made by local distillers Prohibition Distillery and Tuthilltown Spirits Distillery with a dose of Angry Orchard’s fresh pressed apple juice to make it authentic. Dust off your ugliest flannel and party with live music at the Ugly Flannel Party on December 17, from 6–9pm.

Applewood Winery: Santa’s Sauce

Forget milk and cookies, if Santa’s going to deliver presents, he’s going to want something with a little kick at the end of the night. Get into the spirit at Applewood Winery and pick up plenty of Naked Flock‘s Santa’s Sauce, a seasonal favorite infused with notes of cinnamon, cardamom and cayenne. Reserve a private outdoor cabana in advance and celebrate the holidays with up to 10 of your besties around a fire pit.

bottle of cider with holiday decorations
Stock up on Santa’s Sauce at Applewood Winery.

Baldwin Vineyards: Apple-tini Time

Kick off festivities with Baldwin’s Spiced Apple Wine made from local apples, cinnamon and spice. Delicious on its own – chilled, it’s refreshing and zesty, or serve it warm and it’s reminiscent of Grandma’s apple pie. Add a shot of vodka, and you’ll have the best Apple-tini in town. Shed the holiday stress and relax upstairs in the Hayloft or settle in with the family and a board game. Deck the halls at Baldwin on December 10th and 11th for their Annual Santa-Gria Weekend!

Benmarl Winery: Drink History

Benmarl Winery’s 37-acre estate is the oldest vineyard in the United States centered in Marlboro, a charming town with some of the most festive streets and decorated homes in the region. At the winery, warm up with the classics: Cabernet Franc and Reserve Riesling are two of their tried-and-true award winners.

Brotherhood: Take in the Tree

Brotherhood Winery takes the honor as America’s oldest winery. Soak in American wine history on a guided tour and follow it up by a flight of your favorites. The winery takes holiday pomp and circumstance to the next level. Try their sparkling wines and revel in the holiday lights—and legendary tree! Notch up the holiday intrigue and book a ticket for the “Holly Jolly Homocide” Murder Mystery Dinner on December 9th from 7pm to 11pm.

large Christmas tree with holiday lights
A massive tree delights at Brotherhood Winery.

City Winery: Party Down

If you are in the mood for a rock ’n roll holiday, head over to City Winery in Montgomery, where the live music flows like vino in a historic, converted mill. Indulge in delicious fireside meals, paired with local wines and spirits. Shop at the market and pick up one of their winemaker-selected Holiday Gift Sets for the wine lovers on your list. Make is a weekend and spend the weekend in one of the guest suites in The Barn.

Clearview Vineyard: Country Christmas

This Warwick winery offers good old-fashioned country hospitality, live music, and food on the weekends. At Clearview, hard ciders, sangria, beer and good times are always on tap, too. Live music fills the winery every weekend from 2–5pm.

Magnanini Farm Winery: Comfort Food & Drink

End your journey at Magnanini Winery where they serve up hospitality and artisanal wines like Rosso Rivera and Dechaunac to pair with classic Northern Italian dishes. Don’t miss the handmade gnocchi, ravioli, cappoletti, coppa, and prosciutto—or the grappas! Dinners (reservations required) are accompanied by live music, and if the spirits move you, dancing. Save the date for the Winter Festival and tree lighting on December 10th, from 3pm to 8pm, and warm up with a hot drink around the bonfire.

Quartz Rock Vineyard: Winery Wonderland

Quartz Rock Vineyard is turning their winery into a holiday wonderland this year, with live music, festive drinks and treats, fire pits and cozy seating inside and out. Try new releases like the Holiday Bubbly which will be uncorked for the first time this season, alongside their first sparkling cider. Plan to hit their Holiday Open House party on December 10th and 11th.

Robibero Winery: Family Fun

Robibero Winery opens its arms to your entire family with wood-fired pizza, live music, and an outdoor stone firepit nestled on 42 acres in the Gunks. Pair the festivity here with award-winning wines like the New York Rosé and Cabernet Franc, and mark the calendar for the Ugly Sweater Party, a must-do annual event that takes place on December 17th from 11am to 6pm.

Stoutridge Distillery & Winery: Artisanal Innovation

This premium estate winery and distillery in Marlboro has pioneered small-batch, natural wine and spirits production in the Valley since 2000. Stroll the grounds and relax in the tasting room where you can learn all you want to know about Stoutridge’s Certified Green wine and spirits-making process. Come for the wine and warm up with their impressive line-up of award-winning Absinthe and Brandy. (Or vice versa!)

Warwick Valley Winery: Decked out for Fun

Warwick Valley Winery & Distillery has something for everyone. Alongside wine, you’ll find premium fruit ciders and top-shelf bourbons, applejacks and gins (Doc’s is the oldest cidery in New York State, and Black Dirt is the first craft distillery in New York since Prohibition). Sip, shop, and catch live music at the casual and friendly tasting room every weekend, rain, snow or shine.

Whitecliff Vineyard & Winery: Pushing the Envelope

This Gardiner winery consistently earns praise for their terroir-driven wines. Settle in for a flight in the welcoming tasting room, where the knowledgeable staff will guide you through their extensive offerings. If you want to taste—and share with gift recipients—just what the Hudson Valley is capable of, come here for sips of their Merlot Malbec blend, Cabernet Franc, Bourbon Barrel Blonde, and Blanc de Blancs—a local legend.