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  • 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

  • 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

  • The Jinkx and DeLa Holiday Show

    UPAC 601 Broadway, Kingston, NY, United States

    Award-winning drag queens BenDeLaCreme and Jinkx Monsoon return with their wildly acclaimed holiday spectacular, packed with outrageous comedy, unforgettable characters, and plenty of festive chaos. Now in its ninth year, *The Jinkx & DeLa Holiday Show* promises another wildly unpredictable winter adventure that will leave audiences laughing all the way to the North Pole.

    $49.50 – $199.50

  • The Jinkx & DeLa Holiday Show

    UPAC 601 Broadway, Kingston, NY, United States

    The greatest holiday show south of the North Pole is back with another brand spankin’ new wintertide wonder! Award-winning comedy icons, writers, actors, and drag queen powerhouses BenDeLaCreme & Jinkx Monsoon are coming back to town with the wildly successful, internationally acclaimed, “The Jinkx & DeLa Holiday Show.” Throughout the show’s 9-year history, Jinkx and […]

    $49.50 – $199.50

  • The Julie Novak Storytelling Club

    The Julie Novak Storytelling Club
    Good Work Institute 65 St. James Street, Kingston, NY

    Calling all curious, brave humans ready to connect, expand, and have a raucous good time. Inspired by the big, bold spirit of our beloved late co-founder, Julie Novak, TMI Project invites you to step out of this crazy world and into an alternate universe where magic exists, and we remember that being human is a […]

    Free

  • The Julie Novak Storytelling Club

    The Julie Novak Storytelling Club
    Good Work Institute 65 St. James Street, Kingston, NY

    Calling all curious, brave humans ready to connect, expand, and have a raucous good time. Inspired by the big, bold spirit of our beloved late co-founder, Julie Novak, TMI Project invites you to step out of this crazy world and into an alternate universe where magic exists, and we remember that being human is a […]

    Free

  • 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.

  • Uptown Kingston Snowflake Festival

    Uptown Kingston Kingston

    Experience the magic of winter by strolling through charming, historic streets filled with festive decorations, local shops, cozy restaurants, and holiday cheer! Discover the small-town charm, unique finds, and seasonal magic that make Kingston the perfect winter getaway.

    Free

  • Labiahead (all female Radiohead, performing OK Computer in full + other hits!) at Assembly

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

    Labiahead is an all-women collective of powerhouse musicians and Radiohead obsessives. The band includes musician and viral comedian Charlene Kaye (SNL, Succession), Tony award winner Lena Hall (Hedwig on Broadway, Apple TV+’s Your Friends and Neighbors), Meg Toohey (Waitress) on guitars and synths, Lexi Bodick (Shucked) on bass, and Paige Durr (Six) on drums.

  • Hudson Valley Symphony Orchestra

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

    Hudson Valley Symphony Orchestra Strings bring coziness to the chilly season. Concertmaster Carole Cowan will perform "Winter" from Vivaldi's Four Seasons. Hear Corelli's Christmas Concerto, Telemann’s Viola Concerto performed by Assistant Principal Violist Gregory Williams, and much more. Come in from the cold and enjoy a cheerful wintertime concert. This is a perfect event for […]

  • 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