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  • Uncork the Holidays on the Shawangunk Wine Trail

    Uncork the Holidays on the Shawangunk Wine Trail
    Shawangunk Wine Trail NY

    November 21–22, December 5–6, and December 12, 2026 Time: 11 AM–5 PM Five dates, Three winery itineraries, four wineries each, and a festive Hudson Valley holiday experience! Location: Multiple Locations along the Shawangunk Wine Trail, Hudson Valley, NY Celebrate the season with Uncork the Holidays, a festive wine trail experience featuring 12 participating wineries across […]

    $35 – $45

  • Uncork the Holidays on the Shawangunk Wine Trail

    Uncork the Holidays on the Shawangunk Wine Trail
    Shawangunk Wine Trail NY

    November 21–22, December 5–6, and December 12, 2026 Time: 11 AM–5 PM Five dates, Three winery itineraries, four wineries each, and a festive Hudson Valley holiday experience! Location: Multiple Locations along the Shawangunk Wine Trail, Hudson Valley, NY Celebrate the season with Uncork the Holidays, a festive wine trail experience featuring 12 participating wineries across […]

    $35 – $45

  • Uncork the Holidays on the Shawangunk Wine Trail

    Uncork the Holidays on the Shawangunk Wine Trail
    Shawangunk Wine Trail NY

    November 21–22, December 5–6, and December 12, 2026 Time: 11 AM–5 PM Five dates, Three winery itineraries, four wineries each, and a festive Hudson Valley holiday experience! Location: Multiple Locations along the Shawangunk Wine Trail, Hudson Valley, NY Celebrate the season with Uncork the Holidays, a festive wine trail experience featuring 12 participating wineries across […]

    $35 – $45

  • Junior League of Kingston Turkey Trot

    O&W Rail Trail

    A fun and festive community event bringing people together to celebrate the season of gratitude, giving, and togetherness. Whether you’re running, walking, or cheering on participants, it’s a wonderful way to kick off Thanksgiving while supporting the Junior League’s mission to make a positive impact on the local community!

  • Family of New Paltz Turkey Trot

    Water Street Market 10 Main Street, New Paltz, NY

    Kick off Thanksgiving with a fun and festive community tradition that brings families, friends, and runners together for a great cause. Enjoy a morning of movement, community spirit, and holiday cheer while supporting local families in need. And yes… you can have pie after!

    $20 – $30

  • Catskill Mountain Railroad’s Polar Express

    Catskill Mountain Railroad’s Polar Express
    Catskill Mountain Railroad 55 Kingston Plaza Road, Kingston, NY

    Step into the magic of the holiday season aboard the Catskill Mountain Railroad’s Polar Express, where a festive train ride through the Catskills brings the beloved Christmas story to life. Sip hot chocolate, enjoy freshly baked cookies, sing along to holiday favorites, and journey to the North Pole for a special visit with Santa - […]

    $38 – $58

  • Crime on the Hudson: Gilded Age Pirates and River Thieves

    Hudson River Maritime Museum 50 Rondout Landing, Kingston

    Do you ever wonder if there were actual pirates on the Hudson River? Come and learn about a wild chapter in Hudson River history when mercenary sloops prowled the waterway, raiding mansions and plundering merchant ships. The evening will begin with a brief lecture by an HRMM Educator on the real and sometimes legendary criminal […]

    $28

  • Twin Star Orchards Holiday Market

    Twin Star Orchards Holiday Market
    Twin Star Orchards 155 N Ohioville Rd, New Paltz, United States

    Twin Star’s beloved Holiday Market returns for five weekends between Thanksgiving and Christmas! Gather your family and friends, get cozy, and become inspired for gifting season by shopping bespoke yet accessible presents for your loved ones!

  • Catskill Mountain Railroad’s Polar Express

    Catskill Mountain Railroad’s Polar Express
    Catskill Mountain Railroad 55 Kingston Plaza Road, Kingston, NY

    Step into the magic of the holiday season aboard the Catskill Mountain Railroad’s Polar Express, where a festive train ride through the Catskills brings the beloved Christmas story to life. Sip hot chocolate, enjoy freshly baked cookies, sing along to holiday favorites, and journey to the North Pole for a special visit with Santa - […]

    $38 – $58

  • Imagine Art Walk by JEONIJO

    Imagine Art Walk by JEONIJO
    Imagine Art Walk 325 Stanton Lane, Napanoch

    Imagine Art Walk by JEONIJO is an outdoor art experience tucked into the woods of the Hudson Valley. Wander the trail and discover curious creatures, unusual sculptures, found-object creations and unexpected art woven into nature. Opening to the public on Saturday, October 17, Imagine Art Walk will be open select Saturdays from 3–7 PM through […]

    Free

  • Hung With Care (A Very Queer Holiday Spectacular!)

    Assembly Kingston 236 Wall St, Kingston, NY, United States

    The one-night-only performance - featuring some of the nation’s premier burlesque, dance, drag and circus artists - will be hosted by NYC cabaret legend Murray Hill, the self-proclaimed hardest-working middle-aged man in show business. With razor-sharp wit, quickfire ad-libs, and a wink that lights up the stage, Murray has spent decades turning every stage he […]

  • Holiday on The Walkway

    Walkway Over the Hudson State Historic Park 87 Haviland Road, Highland, NY, United States

    Celebrate the season with a festive afternoon filled with seasonal music, candy canes, local holiday art, and fun for the whole family - kids and dogs included! Meet the Brays of Sunshine miniature donkeys, enjoy a children’s craft area hosted by the Walkway Ambassadors, and capture special holiday memories with Jolly Ol’ Saint Nick!

    Free