Shawangunk Wine Trail Events

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.

Shawangunk-Wine-Trail-2-Pack-Summer-Sale. Images showing two women looking at Passport

Hudson Valley Wine Tasting Passport

FINAL SALE OF THE YEAR — ENDS JULY 31
Enjoy a tasting flight at all 13 participating Hudson Valley wineries through Aug. 31. Perfect for couples, friends, and making the most of summer. Purchase two and save $50 with code SUMMER50.

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Summer Sip

July 19, 2026, Admission is FREE! Features live music, lawn games, and delicious food for purchase. Everyone is welcome to enjoy the live music, shop our vendors, food for purchase, and a fun festival atmosphere. Purchase a VIP Tasting Ticket to access the tasting areas.

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Harvest the Hudson

Sept 14-30, 2026
This 17-day event invites you to truly taste the harvest. From bold Cabernet Franc to crisp Riesling, refreshing Seyval Blanc, and more, every tasting showcases the flavors that shine in our cool-climate vineyards.

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Holiday Fineries at the Wineries

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.

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Sip & Shop Holiday Market

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!

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