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Westchester Holiday Bucket List!

Can you believe it’s already the end of the year? Gone in a blink of an eye, 2021 came and went in a flash as we all slowly went back to “normal.” With the holidays coming, we’re also excited that so many Westchester events are back, offering some great ways to celebrate the season while supporting our local arts organizations, merchants, and local merchants.

Please note: Refer to each event website on their specific mask/COVID vaccine policies.

White Plains

Pictures with Santa at The Westchester

Now – December 24 | Various

Kick-off your holiday shopping and get your pictures taken with Santa early at The Westchester. Various prices. 125 Westchester Ave, White Plains, NY 10601.

White Plains Holiday Shopping, Specials, and Fun

December 5 – Dec  19

As part of White Plains Holiday Shopping, several businesses in downtown White Plains are offering specials beginning on Small Business Saturday and ending on the final day of the White Plains Holiday Market (December 19). The White Plains Holiday Market is in partnership with the White Plains BID, the City of White Plains and 914PopUps, featuring over 60 vendors and artisans in individual open-air booths located on Court Street and Renaissance Plaza in downtown White Plains. This unique shopping experience will be open from December 5th through 19th, from 11am to 7pm daily.


Holiday Train Show Greenburgh Nature Center

December 4 – December 5

Experience the wonder of the holiday season by watching the fun and mesmerizing model train displays. Kids will delight in the magic of the trains as the whoosh on by.  Tickets can be purchased in person. 99 Dromore Road. Scarsdale, NY 10583


Santa Photos at Cross County Center

Now – December 24 | Various hours

Capture the memories of your kids’ 1st — or 10th — picture with Santa at Cross County Center. Reservations are strongly recommended and will feature a special sensory photo session on December 5 at 10am and Pet Photos every week on Mondays in December.  Located in the former NY&CO store, across from Michael Kors, 8000 Mall Walk, Yonkers, NY 10704.


Bricktacular at Legoland Discovery Center

November 26 – January 2

Explore a Bricktacular Winter Wonderland at the Ultimate Indoor LEGO Playground this holiday season at LEGOLAND Discovery Center Westchester. Filled with bricktastic holiday-themed building activities, giant LEGO holiday big builds, MINILAND holiday scavenger hunt and holiday dance parties, there’s fun for the entire family! Children (3-12 years old) and adults, starting at $24.99. Ridge Hill Mall, 39 Fitzgerald Street, Yonkers, NY 10710.

Valhalla, NY

Westchester’s Winter Wonderland Drive-Thru Holiday Light Extravaganza

Now – January 2

The magically drive-through from last holiday season is back and will be even bigger than ever this year! Families can enjoy a colorful world of lights, music, and holiday magic as they drive through 1.2 miles of holiday lights, holiday animations, and greetings from a live Santa. New additions that are sure to please kids of all ages this year, include Elf Disco, a Peace on Earth LED display, two 30-foot snowflakes, and a newly enhanced snowstorm central. Bring a mug of hot chocolate and your favorite cozy snacks as you enjoy the holiday joy from the safety (and warmth) of your car. Tickets per vehicle are $25 Off Peak, $35 Peak. Kensico Dam Plaza, 1 Bronx River Pkwy Rd, Valhalla, NY 10595.

Greenwich, CT

13th Annual Greenwich Reindeer Festival & Santa’s Workshop Presented by Jenny Allen/Compass

Now – December 24

Photos with Santa Monday – Friday, 12pm – 6pm. Saturday, 9am – 6pm

The magical wonder of Christmas is alive at the 13th Annual Greenwich Reindeer Festival & Santa’s Workshop. Held at Sam Bridge Nursery,  families visit the “The North Pole on North Street” to take pictures with Santa, meet the reindeer, and experience Santa’s Workshop with letter writing and a reindeer coloring station. The nursery is also your one-stop shop for Christmas trees, lights, ornaments and more. Free admission.



A Charlie Brown Christmas: Live on Stage at Chappaqua Performing Arts Center

December 3-19

A favorite for both kids and adults is anything Peanuts for the holidays. Head over to Chappaqua Performing Arts Center to enjoy this television classic live with all your favorites- Snoopy, Lucy, Linus, and of course, Charlie Brown. Enjoy songs and melodies and more this season

songs and carols.

White Plains

A Christmas Carol at White Plains Performing Arts Center

December 3 – 30

Enjoy this holiday classic right in Westchester at the White Plains Performing Arts Center. First performed at Radio City Musical Hall, this musical version is perfect for kids of all ages to experience Christmas through the classic tale of Ebenezer Scrooge. Tickets range from $39 – $61. 11 City Place, White Plains, NY.

Mount Vernon

African Artisan Market at Luangisa African Gallery

December 4: 10am-7pm

December 5: 12pm-6pm

Shop a collection of handmade, artisan-made goods curated from Africa. Sourced over the past 25 years, you can find jewelry, African art and artifacts, items for the home, bags, fashion, accessories, and more. Free admission. 374 Hawthrone Terrace, Mount Vernon, NY 10552.


914 Orchestra Concert

December 5 at 3pm

Ring in the holiday season with live music, performed by the talented 914 Orchestra.  They will be showcasing holiday favorites — making this a great event for kids of all ages. $30 per person. 8 Sunnyside Avenue, Pleasantville, NY.


Kwanzaa Celebration at the Community Center

December 26th | 3:00pm-6:00pm

Enjoy a celebration of Kwanzaa, family, and culture. Community Center, 71 Columbus Avenue (top floor), Tuckahoe, NY 10707.