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Winter Wonders: Top Events and Festivities in the Hudson Valley & Catskills

Celebrate the season with the best winter festivals and holiday fun across the Hudson Valley

November 03, 2023

Winter in the Hudson Valley and Catskills is pure magic—think twinkling lights, festive markets, snowy adventures, and cozy gatherings that warm the spirit. From holiday parades and artisan fairs to ice skating, seasonal food events, and charming small-town celebrations, the region comes alive with ways to celebrate. Whether you're looking for family-friendly fun or romantic winter escapes, there's something for everyone to enjoy this season.

CATSKILL MOUNTAIN RAILROAD: THE POLAR EXPRESS

Weekends November 17- December 29

Set to the motion picture soundtrack, pajama-clad passengers will be whisked away aboard The Polar Express™ on a magical round-trip journey to the North Pole. The conductor will punch tickets, and chefs will serve hot chocolate, just like in the film. Passengers will also enjoy a sing-along and a special reading of this Van Allsburg classic. Santa will board the train at the North Pole to greet the children and give a special sleigh bell to all those who believe.

Westbrook Lane Station at Kingston Plaza, Kingston
845-332-4854
catskillmountainrailroad.com

MISS BENNET: CHRISTMAS AT PEMBERLEY

December 1-17

One of the most popularly produced plays in the country since its premiere, this hilarious sequel to Jane Austen’s Pride and Prejudice is set two years after the novel ends. 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 equal, and maybe even love.

Shadowland Stages, 157 Canal Street, Ellenville
845-210-4848
shadowlandstages.org/mainstage-season

 

ANNUAL UPTOWN KINGSTON SNOWFLAKE FESTIVAL

December 1, 6-8pm

Usher in the holiday season with Uptown Kingston’s annual Snowflake Festival! Holiday-themed performances, fire twirlers, jugglers, ice carving, horse-drawn carriage rides, a tree lighting, Santa and Mrs. Claus, and so much more throughout the Historic Stockade District. Indoor and outdoor festivities for the whole family! This is a FREE event.

Uptown Kingston
kuba.network/snowflake

SINTERKLAAS FESTIVAL DAY, RHINEBECK

December 2

Sinterklaas is a day-long, colorful celebration that features children’s workshops, dance, theatre, and music all over the village of Rhinebeck. Don’t miss the Dancing Bear, the Pocket Lady, and Mother Holly. The spectacular Children’s Starlight Parade at 6 pm, featuring two-story-tall, animated puppets carried by hundreds of volunteers, closes the day at twilight. A non-denominational event, Sinterklaas joins residents and visitors alike, people of all ages and backgrounds, in a memorable celebration of children, art, and the light of the winter season.

Rhinebeck
sinterklaashudsonvalley.com/sinterklaas-festival-day-in-rhinebeck

 

HOLIDAY PHOTOS WITH THE GRINCH

December 3, 10am-4pm

Are you on the naughty list? Meet & Pose with the Grinch. Pets are welcome but not necessary. Cost of event is by donation: Your donation this year will go to Perfect Pets Rescue and Stray Cat Network. Please give generously. If you or your pet need extra space, please call ahead and sign up for a time slot; otherwise, just come on by.

Pause Dog Boutique
6423 Montgomery Street, Rhinebeck
845-532-0676
montgomeryrow.com/events

ARTISTS & MAKERS HOLIDAY MARKET

December 9 & 10, 11-4pm

Come out for Circle’s fourth annual holiday extravaganza. Get beautiful, locally made gifts for everyone on your list that you can feel really good about. All the 70-plus market vendors here are local artists and artisans. Enjoy live holiday music, yummy food, and festive drinks! Support your neighbors, and find just the right gifts.

At ArtPort Kingston,
108 East Strand, Kingston Waterfront
845-389-8318
circlecreativecollective.org

 

HOLIDAY PHOTOS WITH SANTA

December 10, 10am-4pm

Meet the real Santa, no fake beards here. Holiday Photos with Santa Claus. Pets are welcome but not necessary. Cost of photo/event is by donation: Your donation this year will go to Perfect Pets Rescue and Stray Cat Network. Please give generously. If you or your pet need extra space, please call ahead and sign up for a time slot; otherwise, just come on by.

Pause Dog Boutique
6423 Montgomery Street, Rhinebeck
845-532-0676
montgomeryrow.com/events

HUDSON VALLEY GINGERBREAD COMPETITION

December 10

Show us your incredible gingerbread creations and you could win an overnight stay at Mohonk Mountain House! Join in on the holiday fun with our eighth annual Hudson Valley Gingerbread Competition. From gingerbread steamships, robots, and dinosaurs to the most detailed, exquisite, fairytale houses and cottages – This competition will showcase it all!

1000 Mountain Rest Road, New Paltz
855-883-3798
mohonk.com/competition-details

 

“A HOLIDAY CELEBRATION,” CHAMBER MUSIC PRESENTED BY HUDSON VALLEY BAROQUE

December 16, 2-3pm

Hudson Valley Baroque provides old-style chamber entertainment combined with thought-provoking history education. Space is limited. Pre-registration is highly encouraged! $10 General Admission. $7 Discounted Admission for seniors, students, active military members and their families, veterans, and children under 13. Free for HHS members and children under 6.

Crispell Memorial French Church
60 Huguenot Street, New Paltz
845-255-1660
huguenotstreet.org/calendar-of-events

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