Five dates, Three winery itineraries, four wineries each, and a festive Hudson Valley holiday experience!

November 21–22, December 5–6, and December 12, 2026

Celebrate the season with Uncork the Holidays, a festive wine trail experience featuring 12 participating wineries across three unique itineraries. Choose one itinerary, each featuring four wineries, and enjoy seasonal wine and cider tastings, festive cocktails, delicious flavors, and special holiday experiences along the way.

Your Full Experience ticket includes tasting flights at four wineries along your chosen itinerary and a complimentary Shawangunk Wine Trail tasting glass to take home. You’ll also receive an Uncork Passport featuring seasonal food and wine pairing ideas, holiday wine cocktail recipes, and special offers.

Designated drivers are welcome with a free Designated Driver ticket, which includes four non-alcoholic beverages, one at each winery along the selected itinerary.

Ticket Pricing & Sales: Early Bird tickets are $35 through October 31. Prices increase to $40 on November 1, with an additional $5 increase on the Monday before each scheduled event weekend. Tickets are not available at the door. All ticket sales close at 10 PM on the Friday before each scheduled event dates

Presented by: Shawangunk Wine Trail and sponsored by Visit Vortex Hudson Valley and Radio Woodstock.