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  • 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!

  • 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

  • A Little Wilder

    A Little Wilder
    Material Projects Space 6 Market St, Ellenville, NY, United States

    A Little Wilder brings together Cadence Giersbach, Wendy Hollender, Allyson Levy, Mary Jane Nusbaum, Kelly M O’Brien, Soli Pierce, and Millicent Young for a small works exhibition and holiday pop-up exploring the living world. Gallery works are $450–$1,200, with many more affordable works in the adjoining retail pop-up.

  • 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

  • 5th Annual Holidays in the Hamlet

    Wallkill Public Library 7 Bona Venutra Avenue, Wallkill

    A festive evening filled with local shopping, artisan vendors, holiday performances, and a special visit from Santa. Enjoy the community tree lighting before wrapping up the evening with a dazzling fireworks display at Garrison Park!

    Free

  • A Frosty Fest

    A Frosty Fest
    Headless Horseman Hayrides & Haunted Attractions 778 Broadway, Route 9W, Ulster Park, NY, United States

    Experience the thrill of a festive winter wonderland filled with seasonal fun, dazzling decorations, and holiday excitement for the whole family. Make it a memorable Hudson Valley getaway and discover the magic of the season!

  • A Christmas Carol

    A Christmas Carol
    UPAC 601 Broadway, Kingston, NY, United States

    A timeless performance in the heart of Uptown Kingston! Experience the beloved holiday classic brought to life on stage, filled with festive spirit, memorable moments, and the perfect dose of Christmas nostalgia. Make it part of your holiday getaway and enjoy everything Kingston has to offer this season!

    $21 – $33

  • Charlotte Cornfield & Friendship w/ More Eaze

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

    Charlotte Cornfield is a Toronto singer-songwriter whose heartfelt, full-voiced music explores love, uncertainty, and the transformative experience of motherhood. Joining her are Friendship, a Philadelphia-based band blending country, folk, and indie rock through swirling arrangements, poetic lyrics, and Dan Wriggins’ distinctive, weathered vocals.