The 7 Most Festive Holiday Events in Westchester This December

It’s that time of year, when Westchester brims with the cheerful spirit of the holiday season.

Below, we’ve gathered some of the most magical and merry winter events lighting up the county. 


For the real Tinseltown…

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Westchester’s Winter Wonderland

For holiday cheer on a truly grand scale, give Westchester’s Winter Wonderland a go. This annual event (attended by more than 160,000 to date), offers a sleighful of attractions, including a new Santa’s Village (with live reindeer!) and a 55-foot Ferris wheel, along with a 40-foot heated slide and brand-new circus attractions. Taking place on weekends and select dates from November 29 through January 4 at Valhalla’s Kensico Dam Plaza, the event boasts myriad ways to get into the spirit of the season.

These include a holiday light show, ice-skating rink (identical in size to the one at Rockefeller Center) with free skate rental, amusement rides, and circus acts, all capped by one of Westchester’s tallest lighted Christmas trees. Meanwhile, the Winter Wonderland Holiday Circus presents five nightly performances, such as motorcycle thrill riders doing tricks in a “thunderdome,” a trapeze artist, and a human contortionist. A Wegman’s tent onsite will sell hot cocoa, while the entry fee will include unlimited access to Santa’s Village.


Knock a few names off that gift list…

Lyndhurst Holiday Market

There are plenty of places to score presents in Westchester, but how many shops are situated in the incredibly scenic grounds of Tarrytown’s Lyndhurst mansion? A rite of passage for locals with a penchant for cute crafts and unique finds, The Lyndhurst Holiday Market overtakes the idyllic estate from November 29 through December 1. The weekend event features a carefully curated selection of singular items produced by 50 local and regional artists, makers, and craftspeople. To sweeten the deal, the market, which also boasts seasonal snacks and activities for kids, is free to attend with the purchase of a mansion tour ticket.

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For a gelt of a good time…

Chanukah Town

The celebration of light overtakes Yonkers during this incredible annual event when Ridge Hill is transformed into Chanukah Town. On December 22, visitors can enjoy rides, music, seasonal refreshments, crafts, and entertainment, including a “gelt drop,” as well as the world’s first virtual-reality Chanukah experience.

Not to mention a fun holiday train ride, balloon sculpting, a show by Mario the magician, 3D printing and robotics, as well as a kosher food truck. At the end of the whirlwind day, kick back with a large-scale menorah lighting.


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For a stately seasonal affair…

Holiday Tea Musicale

After braving crowded malls and shopping plazas, a more sedate yuletide event may be just what the doctor ordered. If so, stop by the Caramoor Center for Music and the Arts in Katonah, where the overstimulated can unwind with a classical concert prior to a self-guided tour of the Rosen House and a holiday tea service.

The afternoon event boasts festive decorations, opportunities for holiday sing-alongs, and high tea served in Caramoor’s magnificently appointed Music Room, with finger sandwiches, seasonal treats, and hot chocolate with marshmallows. This year, the traditional event includes a special alternative activity to the self-guided tour, aimed at holiday hounds ages 5 and up, called “I Spy in the Music Room,” as well as a selection of kid-friendly sandwiches, should you have a few picky eaters on your “nice” list.


Travel back to holidays past…

Dickens’s Christmas Carol

No need to find a shrouded spirit in order to travel back to Christmas past. On December 7, 8, 14 & 15, guests can get a little taste of holidays as they were celebrated in 1867, at Sleepy Hollow’s Philipsburg Manor. Take a seat and enjoy a retelling of Charles Dickens’ A Christmas Carol, by storyteller Jonathan Kruk.

Follow along as Ebenezer Scrooge discovers the true meaning of Christmas by way of a handful of ghosts.



Meet the big guy himself…

Simon Santa Photo Experience

The Westchester in White Plains is welcoming Saint Nick in grand style during its Simon Santa Photo Experience. Between November 1 and December 24, Kris Kringle will not only be available for pictures, but children across the special-needs spectum will be able to meet Santa in a sensory-friendly environment during Caring Santa hours on December 1.

The event will also include Pet Photo Nights on select evenings after mall hours, as well as free 30-minute express parking.


For a merry musical…

It Happened One Christmas Eve

Elmsford’s Westchester Broadway Theatre is hosting a bevy of holiday events this month, including a country-music-infused Christmas concert, a Buddy Holly-inspired holiday event, and a yuletide performance by the Edwards Twins. But their longest-running event is their lighthearted new holiday musical, It Happened One Christmas Eve, running November 27 through December 23.

The toe-tapping musical blends celebrated Christmas carols, popular seasonal songs, and original works, all aimed at inspiring holiday cheer, goodwill, and a heaping helping of nostalgia in all those who attend.

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

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