101 Ideas for Holiday Family Fun in Westchester - 2021 | Kids Out and About Westchester

101 Ideas for Holiday Family Fun in Westchester - 2021


KidsOutAndAbout is Westchester's online guide to everything for kids, teens, and families! 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

Multiple Days Starting Nov 19, 2021

(Reservations are strongly recommended)

SANTA PHOTOS - Cross County Center

Multiple Days Starting Nov 19, 2021

Photos with Santa - Stamford Town Center

Nov 26-Dec 24, 2021 (closed Sundays)

13th Annual Greenwich Reindeer Festival - Sam Bridge Nursery & Greenhouses

Multiple Days Starting Nov 26, 2021

Santa at Battenfeld Christmas Tree Farm

Multiple Days Starting Nov 26, 2021

Santa Photos at Ridge Hill

Multiple Days Starting Nov 26, 2021

Photos with Santa at Jefferson Valley Mall

Multiple Days Starting Nov 27, 2021

Pictures with Santa at Rocking Horse Ranch Resort

Nov 28, 2021

Holiday Kickoff with Santa On the Walkway Over the Hudson

Dec 4, 2021 


Dec 5, 2021

Pet Photos with Santa- Stamford Town Center Mall

Dec 5, 2021

Sensitive Santa with Ivy Rehab for Kids - Jefferson Valley Mall

Dec 6, 2021

Paws & Claus - Jefferson Valley Mall

Dec 12 and 19, 2021

Santa Brunch - Powder Ridge

Old-Time Christmas

Multiple dates starting Nov 26, 2021

Twilight Tours at Boscobel

Select Dates Nov 29- Dec 30, 2021

December Classic Mansion Tours at Lyndhurst

Dec 1- 17, 2021


Dec 4, 2021

Carmel NY's Holiday on The Lake

Dec 11, 12, 2021

Christmas In The Village @ Museum Village

Light Displays

Select dates November 19, 2021 through January 9, 2022

Holiday Lights 2021 - Bronx Zoo

Nov 20, 2021

Tree Lighting at Cross County Shopping Center

Multiple Dates Starting Nov 24, 2021

American Museum of Natural History Presents: Origami Holiday Tree

Select Dates Nov 24 - Jan 22, 2022


Multiple Dates starting Nov 25, 2021

Illuminate the Farm at Queens County Farm Museum

Multiple dates beginning Nov 26, 2021

Westchester's Winter Wonderland Drive-Thru Light Show Experience

Nov 27- Jan 3, 2022

Worldwide Lights Celebration at Stepping Stones

Dec 3, 2021

Mt. Kisco Chamber presents: Holiday Tree Lighting

Dec 4, 2021

Holiday Electric Lights Parade and Tree Lighting - Yorktown

Dec 11, 2021


Dec 11, 2021

The Santa Experience & Tree Lighting - Mamaroneck

Holiday Concerts

Sat and Sun Nov 27 - Dec 19, 2021

Holidays in Harmony - Stamford Town Center

Nov 27 and Dec 18, 2021

Industrial Rhythm “Litt Percussion Show” - Stepping Stones

Nov 28, 2021

Yonkers Philharmonic Orchestra at Yonkers Library - WILL BRANCH

Dec 6, 2021

Broadway Unplugged - Holiday Edition - Starring Bryan Perri and Heidi Blickenstaff

Dec 11, 2021

New York Polyphony Sings Sacred Christmas Music - Caramoor

Dec 13, 2021

The Italian Broadway Christmas Show - White Plains Performing Arts Center

Dec 18, 2021

A Virtual Laurie Berkner Family Concert

Dec 18, 19, 2021

Stamford Symphony Holiday Performance at Stamford Town Center

Holiday Theatre

Nov 26-28, 2021 and Dec 26-31, 2021

A Christmas Carol: A Story of Hope - Yorktown Stage

Multiple Dates Starting Dec 3, 2021 A Christmas Carol - White Plains Performing Arts Center
Dec 11, 2021 The Kids Komedian - Stepping Stones
Dec 11 and 18, 2021 Storyteller Jonathan Kruk with Holiday Tales - Boscobel House and Gardens
Dec 18, 2021 Jessica Lynn – A Very Merry Country Christmas - Paramount Hudson Valley
Dec 19, 2021 O. Henry’s The Gift of the Magi at Queens County Farm Museum
Dec 26 and Dec 29, 2021 Jack Frost - Stepping Stones

Holiday Trains

Various Dates Starting Nov 13, 2021

Holiday Train Show - Greenburgh Nature Center

Select Dates Nov 20 - Jan 23, 2022

The New York Botanical Garden Train Show

Starting Nov 27, 2021


Christmas Tree Experience

Opening day Nov 22, 2021

(Closed Thanksgiving Day)

Battenfeld Christmas Tree Farm

Opening day Nov 26, 2021

(Reservations Needed)

Emmerich Tree Farm

Open the Friday after Thanksgiving

Stuart's Fruit Farm

Opening day Nov 27, 2021 

Wilkens Fruit and Fir Farm

Opening day Nov 27, 2021 

Wright Family Farm

Get Moving This Holiday Season

Nov 21, 2021

55th Annual Village of Mamaroneck Turkey Trot

Nov 28, 2020 - Jan 6, 2021 Winter Wonderland Walk at Beardsley Zoo
Dec 11, 2021 Winter Walk - Outdoor Discovery Center
Dec 12, 2021 Annual Skiing & Riding Santa Day at Windham Mountain

Ice Skating

Multiple Days- Starting Nov 2nd, 2021

Public Skating at WSA

Weekends - November 6th- March 6th 2021

(Weather Permitting- Call ahead)

Ice skating at Bear Mountain Rink

Multiple Days starting Nov 20, 2021  

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

Holidays with The Animals

Multiple Dates Starting Dec 4, 2021 Holiday Happenings at Beardsley Zoo
Dec 18, 2021 Beary Merry Holiday at the Trailside Museum & Zoo
Dec 18, 2021 (Virtual) Holiday Virtual Enrichment Program with Wolves!


Nov 28, 2021

Chanukah Menorah Lighting- Bedford

Nov 28, 2021

Menorah Lighting - Carmel, NY

Nov 28, 2021

Chanukah Menorah Lighting - Pound Ridge

Nov 28, 2021

Menorah Lighting - Ridge Hill

Nov 29, 2021

Menorah Lighting at Cross County Shopping Center

Hands On For The Holidays

Nov 26, 2021 Black Friday Art Camp- Creatively Wild
Multiple Dates starting Nov 26, 2021 Holiday Bricktacular! - LEGOLAND Discovery Center Westchester
Dec 11, 2021 Make An Adorable Raccoon With Polymer Clay - Rye Arts Center
Dec 12, 2021 Cookie Make and Take - Muscoot Farm
Dec 17, 2021 Holiday Build – a - Snowman Party - Rye Reads Learning Center

Shopping / Craft Fairs

Nov 6 - Dec 19, 2021 (Saturdays and Sundays)

Art on Market - Ridge Hill

Nov 13, 2021

St. Luke's Holiday Boutique

Nov 13, 14, 2021

Holiday Market at Greenburgh Nature Center

Multiple Days starting Nov 20, 2021

HOLIDAY FOOD TRUCK MARKET at Cross County Shopping Center

Nov 21, 2021

Clay Art Center Clay Holiday Market Opening Event

Dec 2, 2021

Holiday Market- Stamford Museum and Nature Center

Dec 11, 2021

Nyack Holiday Gift Fair

Dec 12 and 19, 2021

Mountainside Holiday Market at Powder Ridge

New Year's Fun

Dec 31, 2021

Cirque De Light – Stepping Stones

Dec 31, 2021 New Year’s Eve Celebration - Windham Mountain
Dec 31, 2021 New Year's Eve Torchlight Parade at Ski Sundown
Dec 31 - Jan 1, 2022 Ring in the New Year at Rocking Horse Ranch Resort


Nov 26, 27, 28, 2021  Holiday Kick-Off - Hudson River Museum
Nov 26, 27, 28, 2021 The Sky Tonight: Holiday Edition planetarium show - Hudson River Museum

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).