The Hottest Events Happening in Westchester This December

Enjoy holiday light shows, festive musical performances, seasonal happenings, and more in Westchester this December.

Ongoing through Dec 22

The Art of Gifting

Knock a few names off that gift list early with locally created one-of-a-kind works during The Pelham Art Center’s 2023 Art Boutique. Find handmade gifts and unique artworks, all produced by area artists and artisans, for sale and on exhibition. Throughout the month, The Pelham Center will also host a number of singular shopping events based upon the show.

Ongoing through Jan 1

Light Fare

Pack the entire family into the car and head to this remarkable way to celebrate the holidays without walking a step. Westchester’s Winter Wonderland overtakes Kensico Dam Plaza each year with a dazzling 1.2-mile drive-through experience featuring thousands of lights and animated displays in the shape of local elves Ned and Albert, not to mention a 100-foot light tunnel, an eye-popping 40-foot Christmas tree, and 50-foot dove.

Westchester Parks Foundation
Photo Courtesy of Westchester Parks Foundation

Dec 9

Luck of the Irish

Traditional Irish music combines with yuletide splendor in this uplifting holiday concert. Taking the stage at Tarrytown Music Hall for a popular annual performance, Cherish the Ladies are a Grammy-nominated Irish super group that has been touring for more than 35 years. This month, they’ll be celebrating the holiday season in style on their A Celtic Christmas tour.

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Cherish the Ladies
Photo courtesy of Tarrytown Music Hall

Dec 9

Cat Walk

Little ones have a fun event to enjoy this winter too, when one seriously cool cat purrs into town. Pete’s Big Hollywood Adventure will hit Mamaroneck’s Emelin Theatre this month, with a lively stage show for all ages that tells the story of Pete and his best friend Callie, who sneak into a Hollywood studio and find themselves suddenly amid the movies.

Dec 10

Sounds of the Season

TENET Vocal Artists proves classical music is alive and well. Returning for their popular annual performance at Caramoor Center for Music and the Arts’ Rosen House, this acclaimed group of vocalists will perform a merry host of internationally beloved European carols interspersed with rare musical gems and surprise arrangements.

TENET Vocal Artists
Photo © Tatiana Daubek

Dec 13

Seasonal Cinema

What holiday season would be complete without a screening of the fan-favorite 1983 flick, A Christmas Story? This hilarious and heartwarming film tells the tale of a boy named Ralphie trying to get the air rifle of his dreams, if only his parents weren’t worried he’d shoot his eye out. Screening for one night only at The Ridgefield Playhouse, this beloved holiday standard still churns up plenty of nostalgia.

Dec 23


Watch in awe as 50 professional dancers bring Tchaikovsky’s immortal work to vivid life during World Ballet Series: Nutcracker. Onstage December 23 at The Palace Stamford, this opulent performance features more than 150 handcrafted costumes flowing before lavish, hand-painted sets, all to tell the seasonal tale of Clara and the gallant Nutcracker who rescues her.

Photo courtesy of Gorskaya-Hartwick Productions, Photo by Jeff Somers

Dec 30–31

Dark Mode

Take a walk on the wild side when Dark Star Orchestra makes its way to Port Chester’s Capitol Theatre for two trippy nights. Known for performing the music of the Grateful Dead over 20 years and more than 3,000 shows, the groovy group is coming to offer local audiences a taste of what made Jerry Garcia’s iconic jam band so great.

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Dark Star Orchestra
Photo by Geoff Tischman

Related: There are the Best Things to Do in Westchester This Week

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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