These Are the Best Holiday Events in Westchester

Sunday Dec. 21, 2025

All day

Port Jefferson Festival of Trees

Ages: 5 – 8
Free
Holiday

Port Jefferson Village CenterPort Jefferson

Various

Holiday Spectacular On Ice

Ages: All
Christmas
Holiday

The Gateway PACSCBellport

Various

Santa Photo Experience at Smith Haven Mall

Ages: All
Christmas
Holiday

Smith Haven MallLake Grove

Various

Santa Photos

Ages: All
Christmas
Holiday

Walt Whitman ShopsHuntington Station

9–10:30am

Labubu Christmas Elf Paint Event

Ages: 5 – 12
Art
Christmas

Key to My ArtAmityville

Baby,Boy,Sitting,On,Santa’s,Lap,At,Christmas,Time.

9:30am–3pm

Brunch with Santa at Desmond’s

Desmond’s Restaurant at East WindWading River

10:15am–noon

Chanukah Chappening

Ages: All
Community
Free

North Shore Jewish CenterPort Jefferson Station

10:30am

Harry Connick, Jr.’s The Happy Elf

Ages: All
Christmas
Holiday

The Argyle Theatre at Babylon VillageBabylon

Various

Santa Claus visit at Tanger Outlets Riverhead

Ages: All
Christmas
Community

Tanger Outlets RiverheadRiverhead

11am–12:30pm

Labubu Christmas Tree Paint Event

Ages: 5 – 12
Art
Christmas

Key to My ArtAmityville

Noon–9pm

Meet Santa at the Tree

Ages: All
Christmas
Free

Huntington Holiday SpectacularHuntington

1–3pm

Winter Wonder Chanukah Party!

Ages: All
Community
Holiday

Center For Jewish Life – Sag HarborSag Harbor

4–6pm

Outdoor Menorah Lighting

Ages: All
Free
Holiday

Montauk Village GreenMontauk

5–8pm

Girl Scouts of Suffolk County’s Holiday Light Show

Camp EdeyBayport

5pm

Sayville Falls Holiday Light Show

Ages: All
Attractions
Holiday

Sayville Falls Mini GolfSayville

+ Export Events

Holiday events in Westchester

Sunday Dec. 21, 2025

Port Jefferson Festival of Trees

Holiday Spectacular On Ice

Santa Photo Experience at Smith Haven Mall

Santa Photos

Labubu Christmas Elf Paint Event

Brunch with Santa at Desmond’s

Chanukah Chappening

Harry Connick, Jr.’s The Happy Elf

Santa Claus visit at Tanger Outlets Riverhead

Labubu Christmas Tree Paint Event

Meet Santa at the Tree

Winter Wonder Chanukah Party!

Outdoor Menorah Lighting

Girl Scouts of Suffolk County’s Holiday Light Show

Sayville Falls Holiday Light Show

Featured Events

17th Annual Greenwich Reindeer Festival & Santa’s Workshop presented by Jenny Allen & Kristen Studwell, Compass Real Estate
Sam Bridge Nursery & Greenhouses

Breakfast with Santa
Kruckers

Holiday Train Show
New York Botanical Garden

Nutcracker Dream
Emelin Theatre

Winter Fest at Cross County Center
Cross County Center

Cross County Center Santa Photos
Cross County Center

Bronx Zoo Holiday Lights
Bronx Zoo

2025 Santa Claus Visit & Photo Session
Jefferson Valley Mall

Santa Photo Experience
The Westchester

Santa Photos at The Mall at Bay Plaza
The Mall at Bay Plaza

Santa Photos at Palisades Center
Palisades Center

Photos with Santa at Nanuet Town Centre
Nanuet Town Centre

What’s Up

Jobs in New York

Add your job

View all jobs…

More from Around NYC

Holden says City Council wants veterans to ‘drop dead’

FDNY Commissioner Robert Tucker officially retires

Sixth Circuit Court rushes to beat Supreme Court in ruling on conversion therapy ban

Beloved Prospect Park swans rescued after suspected off-leash dog attack