Uncork the Holidays: A Fresh Take on a Hudson Valley Holiday Tradition
Shawangunk Wine Trail
October 22, 2026
Uncork the Holidays: A Fresh Take on a Hudson Valley Holiday Tradition
November 21–22, December 5–6 & December 12, 2026
The holiday season is getting a fresh pour! The Shawangunk Wine Trail invites you to celebrate with Uncork the Holidays, a festive wine trail experience featuring seasonal sips, delicious flavors, and special holiday touches at wineries throughout the Hudson Valley.
With 12 participating wineries and three unique itineraries to choose from, you can make the experience your own. Each itinerary features four wineries, giving you a chance to explore a selection of local wineries, discover new favorites, and enjoy the flavors of the season along the way.
Three Itineraries. Four Wineries on Each. Your Holiday Adventure.
Choose the itinerary that fits your style and get ready to celebrate the season!
The Orchard & Vine Trail
Featuring Angry Orchard Cider House, Christopher Jacobs Winery at Penning’s Vineyard, Whitecliff Vineyard, and Robibero Winery.
The Sips & Sounds Trail
Featuring Quartz Rock Vineyard, Benmarl Winery, City Winery Hudson Valley, and Magnanini Winery.
The Mingle & Cheer Trail
Featuring Clearview Vineyard, Brotherhood Winery, Applewood Winery, and Warwick Valley Winery.
Each itinerary offers its own mix of winery experiences, so whether you’re planning a day with friends, a holiday outing with your favorite person, or a seasonal getaway close to home, there’s a trail to explore.
Seasonal Sips and Festive Experiences
Uncork the Holidays is all about celebrating the season; one stop at a time. Along your chosen itinerary, enjoy wine and cider tastings, seasonal cocktails, delicious flavors, and special holiday experiences at each winery.
Look forward to festive drinks and seasonal touches that make each stop unique. Your experience also includes a complimentary Shawangunk Wine Trail tasting glass to take home.
And don’t forget your Uncork Passport! The passport adds another reason to explore, with seasonal food and wine pairing ideas, holiday wine cocktail recipes to try at home, and a special offer for the Shawangunk Wine Trail’s Sip & Shop Holiday Market.
There’s also an opportunity to earn a complimentary VIP tasting ticket to Sip & Shop at City Winery Hudson Valley on December 13. Tasting ticket holders who purchase a total of 12 or more bottles of wine, cider, or spirits from participating wineries between November 21 and December 12 will qualify for a free VIP tasting ticket, a $50 value. Purchases can be combined across participating wineries and visits.
Make It a Holiday Outing
Uncork the Holidays is a great opportunity to gather friends, discover local wineries, enjoy seasonal drinks, and make new holiday traditions. Choose your preferred date and itinerary, select your starting winery and start time, and get ready for a festive day on the Shawangunk Wine Trail.
Designated drivers can join the fun, too, with a free Designated Driver ticket that includes four non-alcoholic beverages, one at each winery along the selected itinerary.
Early Bird Tickets Are on Sale Now!
Uncork the Holidays takes place November 21–22, December 5–6, and December 12, 2026. Early Bird Full Experience tickets are $35 through October 31. Prices increase on November 1, so don’t wait to plan your holiday outing!
Choose your itinerary, gather your friends, and get ready to Uncork the Holidays.
For event details and updates, visit the Shawangunk Wine Trail website and follow us on social media @gunkswine on all platforms.