Sip your way through the seasons on the Shawangunk Wine Trail! Earth Day Weekend kicks off spring, Summer Sip brings wine, cider, music, and food in July, Harvest the Hudson celebrates the fall grape harvest in September, and Holiday Fineries and our Sip & Shop Holiday Market wraps up the year in festive style, Plus, explore it all January–August with the Hudson Valley Passport!
Each event offers unforgettable wine tastings, festive themes, and the perfect opportunity to explore our local lodging, dining, and transportation partners, click here to learn more. Tickets sell fast—plan your getaway and join the fun!
Get updates on the Wine Trail and all member winery events! Sign up for our monthly e-news, click here and follow @gunkswine on Facebook and Instagram.
September 14–30, 2026
Explore six Hudson Valley wineries and discover the distinctive wines of our cool-climate region. Enjoy exclusive tasting flights featuring bright Cabernet Franc, lively Riesling, crisp Seyval Blanc, and more—all at your own pace.
Nov 21-22, Dec 5-6, Dec 12, 2026
Unwrap the magic of the Hudson Valley’s Coziest Holiday Tradition! Guests embark on a merry tasting adventure, enjoying seasonal wine and cider flights, cozy atmospheres, and keepsake at each stop along their chosen itinerary.
Dec 13, 2026
Join us for our 2nd Annual Sip & Shop Holiday Market at City Winery Hudson Valley in Montgomery. Bringing together local artisans, festive flavors, live music, and the award-winning wineries of the Shawangunk Wine Trail, all under one cozy roof!