Holiday Happenings: Fun Things to do this November and December in Westchester

Holiday Happenings!

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 organization merchants, and local merchants.

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



Family Day: Connecting Communities
134 Jay Street, Katonah, NY, 10536.
November 6 | 11:30am, 1:00pm, or 2:30pm (Ticketed times)

Enjoy an afternoon of artistic expression with themes of family heritage and shared American experiences. This interactive event includes art-making led by artists Sara Rahbar and Thuan Vu as well as the opportunity to listen to immigration-centered picture books from guest readers, and enjoy several activities.Members are free. Non-members: Adults $10. Seniors, students and children (12 and under) $5.

White Plains

Pictures with Santa at the Westchester
November 12 – December 24 | Various
125 Westchester Ave, White Plains, NY 10601.

Kick off your holiday shopping and get your pictures taken with Santa early at The Westchester. Various prices.


Holiday Artisan Market at the Ossining Public Library
53 Croton Avenue, Ossining, NY.
November 20 | 10:00-4:00pm

Tis’ the season with a handmade, artisan made gift, featuring soaps, jewelry, pottery, accessories and more — all made by the Northeast Etsy Artists Collective with a portion of the sales benefiting the Friends of the Ossining Public Library. Free admission.


Holiday Market at Greenburgh Nature Center
99 Dromore Road. Scarsdale, NY 10583
November 13 – November 14 | 10am-3pm 

Shop local this holiday season at the 14th annual Holiday Market! Held outside, the outdoor arts & crafts fair showcases local vendors and artists from Westchester, including Finch Land Beauty LLC, Fizzle Pop Puppet Shop, Jules Mindful Mixtures, Nicole Jurain Pottery, Picture Book, and many more. This is also the opening weekend of the holiday train show where the kids can soak in the magic as their favorite trains zip by. Note: All individuals must wear a mask. Free admission, RSVP to attend.

Holiday Train Show Greenburgh Nature Center
99 Dromore Road. Scarsdale, NY 10583
November 13 – November 14
November 20 – November 21st
November 27 – November 28
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.


Santa Photos at Cross County Center
8000 Mall Walk, Yonkers, NY 10704
November 19 – 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.

Holiday Tree Lighting at Cross County Center
8000 Mall Walk, Yonkers, NY 10704
November 20 | 6-8pm

Enjoy the magic of holiday lights with the lighting of the largest holiday tree in Westchester at the Cross County Center! Standing over 40-feet tall, the tree includes over 20,000 LED lights that shoppers can walk-thru and take pictures all season long. The kick-off date includes live musical and dance performances, along with ice skating special characters, strolling entertainers, and an electronic train ride. Free admission.

Bricktacular at Legoland Discovery Center
Ridge Hill Mall, 39 Fitzgerald Street, Yonkers, NY 10710
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.

Menorah Lighting at Cross County Center
8000 Mall Walk, Yonkers, NY 10704.
November, 28 at 6pm

Celebrate the season of lights with a Chanukah Menorah Lighting with the Chabad of Yonkers at the Cross County Center. The Chabad Rabbi will light the menorah, along with music, dancing, and treats. The event will take place near Macy’s. Free admission. 

Valhalla, NY

Westchester’s Winter Wonderland Drive-Thru Holiday Light Extravaganza
Kensico Dam Plaza, 1 Bronx River Pkwy Rd, Valhalla, NY 10595.
November 26 – 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.

Greenwich, CT

13th annual Greenwich Reindeer Festival & Santa’s Workshop 
Presented by Jenny Allen/Compass
November 26 – 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
11 City Place, White Plains, NY.
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.

Mount Vernon

African Artisan Market at Luangisa African Gallery
374 Hawthorne Terrace, Mount Vernon, NY 10552
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.


914 Orchestra Concert
8 Sunnyside Avenue, Pleasantville, NY
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.


Kwanzaa Celebration at the Community Center
71 Columbus Avenue (top floor),Tuckahoe, NY 10707
December 26th | 3:00pm-6:00pm

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