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The Magic of the Holidays in Westchester County

10 ways to enjoy the most wonderful time of the year in this charming region just outside of New York City.

westchester holidays

(Photo: Wolf Conservation Center)

Residents and visitors can experience a new side of Westchester County in winter. As the cooler air blows in, Sleepy Hollow sheds its spooky shroud and villages turn into scenes straight out of a holiday movie. The gentle jingle of boutique shop doors opening and closing fills the sidewalk air, and like all magic winter holiday destinations, the trees and lanes twinkle with lights on dark New York evenings.

Whether you’re escaping the city for a day or a week this holiday season, you’ll find something to do in Westchester County.

Ice Skating

Is there anything that says holiday fun like lacing up your skates and gliding across a frozen pond? Westchester County has several ice skating locations to add to you winter to-do list.

For blustery outdoor fun, head to Wampus Pond Park in Armonk. If the pond isn’t frozen in time for Christmas ice skating, try cross-country skiing through the adjacent forest instead. No matter which activity you choose, remember to bring your own equipment and check for signs indicating safe conditions.

If your family prefers indoor skating, head to Playland Ice in Rye or the Westchester Skating Academy in Elmsford.

Sledding and Tubing

Did you know that many golf courses open for sledding and tubing after golf season has ended?

Grab your favorite toboggan and gather with family and friends to get your thrills on the hills at Mohansic Golf Course or one of the other pristine greens in Westchester County.

If you prefer the wilds of a park, head to Gedney Park in New Castle. The popular snow hill there requires helmets to keep everyone safe and sound for the holidays.

westchester

Beyond a Change of Scenery

Whether you’re looking for a day surrounded by nature or a weekend of festive fun, there’s no place like Westchester County this time of year.

Explore Westchester

Holiday Shopping

For boutique holiday gifts, head to the main drags of Rye, Tarrytown, Katonah and other Hudson River villages and towns. If you’re looking for a one-stop treasure trove of gift possibilities, don’t miss some of this affluent area’s most beautifully decorated shopping malls in winter:

Winter Walks With Wolves

Take a walk on the wild side this December at South Salem’s Wolf Conservation Center. Though they’re not exactly reindeer, these majestic creatures will help you view winter’s beauty with new eyes. Winter activities include full moon walks for the family and evening howls for the grown-ups.

If you happen to celebrate the holidays during the full moon, head to Wolf Conservation Center to learn about the center’s heartwarming work saving these endangered beasts for future generations. If that’s not the holiday spirit, what is?

holidays in westchester

(Winter Wonderland Drive-Thru. Photo: Westchester Parks Foundation)

Westchester’s Winter Light Show

Every year, New York residents pile into their cars to drive through Westchester’s Winter Wonderland Drive-Thru Experience. One of the most dazzling winter wonders of the county, the 1.2-mile road will take you through thousands of magical, animated light displays that are topped off by the biggest Christmas tree in all of Westchester.

If you’re coming from Manhattan, why not stop for hot chocolate and holiday treats at Martine’s Fine Bake Shoppe along the way? This European-style bakery in Tuckahoe will fill your senses with the tastes and smells of the holidays.

“A Christmas Carol”

If live entertainment embodies the magic of the holidays for you and yours, you won’t want to miss “A Christmas Carol.” The White Plains Performing Arts Center Mainstage Productions – a collection of both union and non-union players from Broadway and more – will present Charles Dickens’ holiday tale of Ebenezer Scrooge, Dec. 3 through 30. In addition to the high-caliber talent of the actors and actresses, these productions include live orchestras and lush, professional costumes and set designs. Get your tickets soon!

Tarrytown Music Hall festivities

For more live holiday entertainment in Westchester County, check out the 165-year-old Tarrytown Music Hall for a variety of winter holiday shows. The building itself is worth a visit simply to soak in its warmth and history. The 843-seat venue has housed everything from dance performances to films in its time – all within a structure of gorgeous architecture and acoustic thoughtfulness. Peek in for a warm reprieve from a snowy December afternoon or snag a ticket for a holiday concert this year. You won’t regret it.

Make Spirits Bright

The winter festive season would not be complete without drinking and feasting with dear family and old acquaintances alike. For kid-free festivities, indulge in the many craft beverages available in Westchester County.

Feasts for the Holidays

Whether you’ve whiled the holiday away shopping, sledding or sipping, the perfect way to end a December day in Westchester County is with delicious, belly-warming winter fare.

Taste-test your way through Hudson River villages at dining establishments like The Bit for comfort foods, Half Moon for riverside dining or Saint George Bistro for Old World French fare – perfect for a formal holiday dinner.

Cozy Inns and Hotels

Amp up the holiday cheer by resting your head in lodging with a crackling fireplace at one of the area’s coziest hotels. Feel like royalty at Castle Hotel & Spa, a 19th-century Tarrytown estate that was designed to look like a castle. Or retreat to the historic and elegant Crabtree’s Kittle House in Chappaqua, home to one of the area’s top farm-to-table restaurants. For comfort with a more modern vibe, The Opus Westchester is conveniently located in White Plains near city transportation and boasts the largest spa in the county.

Just know, the warmth and charm of this area during Hanukkah, Christmas, and Kwanzaa might have you ringing the front desk for an extended stay.

Start planning your holiday trip to Westchester County today.  

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