Holiday Fineries at the Wineries – Shawangunk Wine Trail

Shawangunk Wine Trail NY

Bust out your fun seasonal attire or ugly sweater (not required, but encouraged) and get a jump on your holiday wine shopping. Choose your date, itinerary, and starting winery, then head out on a self-guided wine tasting tour! Ticket includes a wine tasting glass, tasting flight at four wineries, and ornaments from each winery.

$35
Event Series Winter Market

Winter Market

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

Shop local artisanal ciders and wines every Saturday and Sunday at the Twin Star Orchard farm market.

Reindeer Ramble

YMCA of Kingston & Ulster County 507 Broadway, Kingston

40th Annual 5K Holiday road run for the whole family. Fun Holiday attire encouraged! Rain/snow/shine. Benefits YMCA Strong Kids Scholarship Fund.

$15 – $25

Kingston Model Railroad Club Train Show – 86th Anniversary

Kingston Model Railroad Club 49 Susan Street, Kingston, NY

A complete "O" scale railroad system in action. Scale models of steam and diesel locomotives. Antique and modern trains. Complete villages and scenery modeled after the Hudson Valley. Railroad museum, trolleys, circus train, Thomas he Tank Engine. New members wanted. No restrooms available. Cash only.

$2 – $6

Saugerties Holiday in the Village

Village of Saugerties Main and Partition Streets, Saugerties, NY

Horse-drawn carriage rides, holiday raffle, live entertainment, caroling, and a decked-out Kiersted House, where Santa is ready to greet you! Please visit event website for specifics and schedule.

The Polar Express – Catskill Mountain Railroad

Catskill Mountain Railroad 55 Kingston Plaza Road, Kingston, NY

Relive the classic story aboard THE POLAR EXPRESS™ for a magical trip to the North Pole where Santa and his Elves board the train to greet guests. Hot chocolate and a delicious cookie served by dancing chefs on your trip. Caroling and on-board entertainment. Train ride lasts approximately one hour. Reserve your timeslot in advance! […]

$34 – $53
Event Series Miss Bennet: Christmas at Pemberley

Miss Bennet: Christmas at Pemberley

Shadowland Stages 157 Canal Street, Ellenville, NY, United States

Shadowland Stages offers a delightful holiday comedy for the whole family! Bookish Mary has grown tired of her role as the dutiful middle sister in the face of her siblings’ romantic endeavors. But things change when an unexpected guest shows up for the family’s Christmas gathering at Pemberley, sparking Mary’s hope for independence, an intellectual […]

$35 – $43
Event Series A Frosty Fest

A Frosty Fest

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

Hudson Valley's Largest Holiday Lights Spectacular! Enjoy the drive-thru experience in the comfort of your own vehicle. Park and walk inside, visit Santa, dance with Mr. & Mrs. Frosty, Rudolph, Snow Bear, and other Characters. Watch Jingles Magic Show, and more. All included with each ticket!

Check website for ticket availability and pricing
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