• Wintertide 2025

    The Kingston Waterfront 1 Broadway, Kingston, NY, United States

    Wintertide is coming! Celebrate the season Saturday, November 29th, 11AM–7PM on the Kingston Waterfront- come down for a festive day of fun, shopping, and community spirit! Participating stores will be offering special discounts, giveaways & hosting fun, free events with something for everyone.  Tree Lighting at Dusk at the foot of Broadway — sponsored by […]

  • A Frosty Fest

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

    Features a drive-thru display of holiday lights and animations with music and holiday decorations, as well as Santa, your favorite characters, magical comedy show, and much more! For more information & pricing, please see https://afrostyfest.com/.

    $
  • Holiday Fair

    1895 South Rd, Poughkeepsie, NY NY, United States

     Holiday Fair at Hudson Valley Pickleball  65+ LOCAL ARTISTS & VENDORS!!  Photo-op with SANTA 12-2PM: Caroling by Our Lady of Lourdes High School  Sunday, Nov 30th 9AM – 4PM 1895 South Road, Poughkeepsie, NY Shop local this season and find the perfect gifts: toys, clothing, jewelry, crafts, and more! 

  • Chambers School Holiday Craft Market

    Chambers Elementary School 945 Morton Blvd, Kingston, NY, United States

    Chambers School is hosting its 4 Annual Craft Market! Come by to see many local vendors, food trucks, and even some student crafters! There is no entrance fee for their event.

    FREE
  • Christkindlmarkt

    Kingston Maennerchor and Damenchor 37 Greenkill Avenue, Kingston, NY, United States

    Join for their annual Christkindlmarkt! Always a favorite of so many, they have handmade items from local vendors plus a variety of cafe items for a shopping time treat! Come and check them out, it will surely get you in the holiday mood! Free entry, no rsvp needed but it does help them with food […]

  • Kids’ Toy Swap hosted by the KCSD Green Team

    Good Work Institute 65 St James St., Kingston, NY, United States

    This holiday season, don’t shop — swap! Join for a free community Holiday Toy (and kids’ winter wear) Swap on December 6, hosted by the KCSD Green Team! What to Bring:Gently used toys and kids’ winter clothing. Please make sure items are clean, not missing any parts, and in good condition. How it Works:Drop off […]

    FREE
  • Sinterklaas Day and Dutch Holiday Traditions Children’s Program

    Mesier Homestead 2 Spring St.,, Wappingers Falls, NY, United States

    At this fun family event you’ll discover the history of Sinterklaas and learn about the holiday traditions that the early Dutch settlers brought with them to New Netherland. Learn how Sinterklaasavond (St. Nicholas eve) was celebrated in the home, and taste some of the tradition Dutch sweets which were part of the festivities. There will […]

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  • Ugly Sweater Public Skate

    Kiwanis Ice Arena 6 Small World Ave., Saugerties, NY, United States

    Join Kiwanis Ice Arena on Saturday, December 6th for an Ugly Sweater Public Skate from 3-4:30pm. There will be an ugly sweater contest, a raffle, a visit from Santa, and lots of skating!! Cost: $10/person & $3/Skate Rental

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  • Jingle Bell Pony Party

    Juckas Riding Stables 1204 NY-302, Pine Bush, NY, United States

    Pony ride option: Enjoy a pony ride, pictures with Santa, visit their petting zoo and have a cup of hot chocolate - $33 per child (age 3 and up). Trail ride option: For kids 7 and up and adults, take a 30-minute horseback trial ride for $50 per person. Picture with Santa, visit petting zoo […]

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  • Ready, Set, Sleigh – 42nd Annual Reindeer Ramble Run!

    YMCA of Kingston and Ulster County 507 Broadway,, Kingston, NY, United States

    The YMCA Reindeer Ramble 5K has been more than just a run — it’s been a celebration of community, wellness, and giving back. This festive, family-friendly event brings together runners and walkers of all ages to enjoy the season while supporting the YMCA’s mission to strengthen the foundations of community. Proceeds from the Reindeer Ramble […]

  • Children’s Storytime: “A Christmas Carol”

    Wilderstein Historic Site 330 Morton Rd,, Rhinebeck, NY, United States

    Join for a special event for families featuring the reading of A CHRISTMAS CAROL, hot chocolate and seasonal refreshments, followed by the opportunity to experience the beautifully decorated Wilderstein mansion. Recommended for ages 5 to 10. All children must be accompanied by an adult. Register online at wilderstein.org/calendar/ or call their Wilderstein Office at 845-876-4818 […]

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  • Catskill Ballet Theatre Presents The Nutcracker

    Ulster Performing Arts Center 601 Broadway, Kingston, NY, United States

    For four decades, Catskill Ballet Theatre’s The Nutcracker has been a cherished part of the Hudson Valley’s holiday season, enchanting audiences of all ages with its timeless story, magical sets, and stunning choreography. This anniversary year promises to be a milestone celebration of artistry, tradition, and community. “We are thrilled to mark our 40th anniversary […]

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