Your Guide to Family-Friendly Holiday Events in Westchester County

The most wonderful time of the year is headed our way, and Westchester County is bustling with holiday shopping pros, seasonal fun seekers, and holiday light display lovers. If you’re looking for family-friendly things to do in Westchester County, look no further – we’re here to be your guide.

Family-Friendly Holiday Events Near White Plains, NY

Holiday Light Displays

Westchester’s Winter Wonderland Drive-Thru Holiday Light Extravaganza at Kensico Dam Plaza in Valhalla is the perfect place to make memories with your friends, family, and grandkids! Drive through 1.2 miles of lights.

Don’t forget to search for downtown Christmas tree lighting and Menorah lighting ceremonies as the season nears!


Many local towns host holiday parades like the White Plains Holiday Parade, featuring bands, floats, and costumed characters.

Festive Performances

There are plenty of holiday-related performances around the area. From children’s concert choirs, theater events, or even caroling, there’s something to suit everyone’s preferences.

Still trying to figure out where to start? Try the Westchester Broadway Theatre for a holiday-themed show or musical, or check out The Westchester Ballet Company for performances of favorites like The Nutcracker.

Holiday Markets and Shows

Holiday markets abound when the season begins! Check out the Hastings Flea Holiday Market in Hastings-on-Hudson or the Greenburgh Nature Center Holiday Train Show.


Attend the Annual Greenwich Reindeer Festival, located at Sam Bridge Nursery Greenhouses at 437 North Street, Greenwich, CT. This event begins on November 24 and ends on December 23, so it’s the perfect way to celebrate the beginning of the season and all the way through it!

Santa Sightings

The holiday season wouldn’t be the same without a visit with Santa. Visit the Cross County Center at 8000 Mall Walk in Yonkers, NY, to see Santa.

Ice Skating

Ice skating rinks make you feel like you’re in a true winter wonderland. Watch the grandkids skate at the Cross Country Center. Want to travel a little further? The Rink at Rockefeller Center in New York City is an iconic place to skate.

Events at Waterstone of Westchester

There is always something going on within our community, too! Enjoy our fun activities with your grandchildren, invite the family to savor a delicious dinner, relax in your residence, enjoy social hour or movie night with friends, or partake in a compelling lifelong learning program.

Make Waterstone of Westchester Your Home for The Holidays and Beyond

With a wealth of things to do right here at our community and in the surrounding area, Waterstone of Westchester is the perfect place to enjoy the holidays – and a fulfilling lifestyle year-round. Give us a call to learn more about life at our luxury senior living community.