(Somewhat fewer than) 101 Ideas for Holiday Family Fun in Westchester - 2020 | Kids Out and About Westchester

(Somewhat fewer than) 101 Ideas for Holiday Family Fun in Westchester - 2020


KidsOutAndAbout is Westchester's online guide to everything for kids, teens, and families! Typically we list (MORE than) 101 ideas for holiday family fun, but. . . it's 2020, which means a bit less is happening than usual. The activities we've listed here are confirmed for this year, but many require reserving ahead of time, so click through to make arrangements. Enjoy the holidays!

If we're missing an activity that should be on our list, please email Mindy Mangan at mindy@kidsoutandabout.com. Please make sure to include a link to the event when you email. Thank you!

Below are items that have been posted to our calendar. If you are affiliated with a business hosting a holiday event that should be on our calendar, we'd love to see it there... it's free to postClick here for instructions about how to add your organization to our list and easily post your events to our calendar!

If you don't already receive our free weekly e-newsletter for Westchester, sign up today to make sure you're in the know about free stuff, festivals, classes, camps, vacation ideas, and all the best events near you! In the meantime, enjoy the ideas below for holiday family fun!

Santa Sightings

Nov 27 - Dec 22, 2020

12th Annual Greenwich Reindeer Festival - 2020

Nov 27, 2020 

Santa's Grand Arrival at Galleria at White Plains

Dec 5, 2020 


Old-Time Christmas

Multiple dates starting Nov 29, 2020

Twilight Tours at Boscobel

Dec 5, 6, 12, 13, 2020

Christmas In The Village @ Museum Village


Light Displays

Starting Nov 13, 2020

New Christmas Tree at Cross County Shopping Center

Select dates November 20, 2020 through January 10, 2021

Holiday Lights 2020 - Bronx Zoo

Multiple dates beginning Nov 27, 2020

Westchester's Winter Wonderland Drive-Thru Light Show Experience

Multiple dates starting Nov 28, 2020

North Kensico Christmas Light Show ***FINAL YEAR***

Dec 5, 2020


Dec 4, 2020 

Mt. Kisco Chamber presents: Holiday Tree Lighting


Holiday Theatre

Saturdays & Sundays Nov 24- Jan 1, 2020 


Dec 12, 2020 (Virtual Event) Livestream-TENET Vocal Artists - Caramoor


Christmas Tree Experience

Opening day Nov 21, 2020

Emmerich Tree Farm

Opening day Nov 23, 2020

Battenfeld Christmas Tree Farm

Opening day Nov 28, 2020 

Wilkens Fruit and Fir Farm

Opening day Nov 28, 2020 

Wright Family Farm

Open the Friday after Thanksgiving

Stuart's Fruit Farm


Ice Skating

Multiple Days starting Nov 14, 2020 

Ice skating at Bear Mountain Rink

Multiple Days starting Nov 11, 2020  

Pop-Up Holiday Ice Skating Rink at Cross County Shopping Center

Multiple Days Nov 29 - Jan 4, 2020

6th Annual Westchester Winter Wonderland with Tree Lighting Celebration

Multiple Days- Dec 23- Jan 3, 2020

Learn to Skate at WSA

Multiple Days- Dec 23- Jan 3, 2020 

Hockey Camp at WSA


Dec 10, 2020

Chanukah Menorah Lighting- Bedford

Dec 13, 2020

Young Families Chanukah Celebration at Congregation Emanu-El of Westchester


Shopping / Craft Fairs

Nov 7, 2020

Holiday Market at Greenburgh Nature Center

Multiple Days starting Nov 27, 2020 

HOLIDAY FOOD TRUCK MARKET at Cross County Shopping Center

Dec 1 - 24, 2020 (Virtual Event)

Virtual Greenwich Holiday Stroll, 24 Days of Holiday Shopping & Dining Dec 1-24

Nov 23 - Dec 1, 2020

Online Artisan Boutique: Unique & Handmade Gifts - Rye Arts Center


New Year's Fun

Dec 31, 2020 New Year’s Eve Celebration - Windham Mountain



Nov 28, 2020 - Jan 6, 2021

Winter Wonderland Walk at Beardsley Zoo

Starting Dec 4, 2020 


Dec 4, 2020 

Outdoor Adventures: Family Night Hike at SM&NC

Below are events that have been posted to our calendar. If you know of an upcoming event that is not yet there, please mindy@kidsoutandabout.com to let her know about it. If you are sponsoring an upcoming event, click here for posting instructions (it's free).