Things to do in Upstate NY | Page 14 of 20

Things to do in Upstate NY

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Saturday Dec. 20, 2025

wf-calendar-The-Great-Holiday-Train-Show-2025-11

10 am – 4 pm

The Great Holiday Train Show

New Castle Historical Society

rp-calendar-Holiday-Bricktacular-at-LEGOLAND-New-York-Resort-2025-11

11 am – 5 pm

Holiday Bricktacular at LEGOLAND New York Resort

Ages: 3 – 12
Attractions
Christmas
Family

LEGOLAND New York ResortGoshen

GrinchBanner

11 am – 1:20 pm

How the Grinch Stole Christmas

Ages: All
Art
Christmas
Family

Jacob Burns Film CenterPleasantville

cross county 2

Noon – 8 pm

Cross County Center Holiday Food Truck Market

Cross County CenterRiverside

1 pm

Breakfast with Santa

600x400_nutcracker dream

1:30 – 3 pm

Nutcracker Dream

Ages: All
Christmas
Dance
Family

Emelin TheatreMamaroneck

post ready YS

2:30 – 3:30 pm

The Nutcracker for Kids

Ages: All
Family
Holiday
Theater

Yorktown Stageyorktown heights

600x400_nutcracker dream

5 – 6:30 pm

Nutcracker Dream

Ages: All
Christmas
Dance
Family

Emelin TheatreMamaroneck

Sunday Dec. 21

All day

Santa Photo Experience

The Westchester

Watson Adventures

8 am – 5 pm

Watson Adventures’ Murder at the Met Scavenger Hunt

The Metropolitan Museum of Art

9 am

Breakfast with Santa

10 am – 7:30 pm

Bear Mountain Ice Rink

Bear Mountain Ice Rink

10 am – 3 pm

Holidays on the Hill Annual Train Show

Lasdon Public Gardens & Veterans MemorialKatonah

wf-calendar-The-Great-Holiday-Train-Show-2025-11

10 am – 4 pm

The Great Holiday Train Show

New Castle Historical Society

11 am – 7 pm

Pop-Up Ice Skating Rink

Ages: 5 and up
Attractions
Family

Cross County Center

rp-calendar-Holiday-Bricktacular-at-LEGOLAND-New-York-Resort-2025-11

11 am – 5 pm

Holiday Bricktacular at LEGOLAND New York Resort

Ages: 3 – 12
Attractions
Christmas
Family

LEGOLAND New York ResortGoshen

cross county 2

Noon – 8 pm

Cross County Center Holiday Food Truck Market

Cross County CenterRiverside

Nutcracker-short-and-sweet-9_cda6c2

1 – 2 pm

Nutcracker, Short & Sweet- Sensory Friendly Performance

Ages: All
Christmas
Dance
Family

Paramount Hudson Valley TheaterPeekskill

1 pm

Breakfast with Santa

Nutcracker-short-and-sweet-9

1 – 2:30 pm

Nutcracker, Short and Sweet

Ages: All
Family

Paramount Hudson Valley TheaterPeekskill

600x400_nutcracker dream

1:30 – 3 pm

Nutcracker Dream

Ages: All
Christmas
Dance
Family

Emelin TheatreMamaroneck

ItsAWonderfulLife (1)

2 – 4 pm

It’s a Wonderful Life

Ages: All
Christmas
Family
Film

Jacob Burns Film CenterPleasantville

Nutcracker-short-and-sweet-9

5 – 6 pm

Nutcracker, Short & Sweet

Ages: All
Christmas
Dance
Family

Paramount Hudson Valley TheaterPeekskill

600x400_nutcracker dream

5 – 6:30 pm

Nutcracker Dream

Ages: All
Christmas
Dance
Family

Emelin TheatreMamaroneck

Monday Dec. 22

All day

Santa Photo Experience

The Westchester

Watson Adventures

8 am – 5 pm

Watson Adventures’ Murder at the Met Scavenger Hunt

The Metropolitan Museum of Art

10 am – 9:30 pm

Pop-Up Ice Skating Rink

Ages: 5 and up
Attractions
Family

Cross County Center

rp-calendar-Holiday-Bricktacular-at-LEGOLAND-New-York-Resort-2025-11

11 am – 5 pm

Holiday Bricktacular at LEGOLAND New York Resort

Ages: 3 – 12
Attractions
Christmas
Family

LEGOLAND New York ResortGoshen

600x400_nutcracker dream

1:30 – 3 pm

Nutcracker Dream

Ages: All
Christmas
Dance
Family

Emelin TheatreMamaroneck

600x400_nutcracker dream

5 – 6:30 pm

Nutcracker Dream

Ages: All
Christmas
Dance
Family

Emelin TheatreMamaroneck

Tuesday Dec. 23

All day

Santa Photo Experience

The Westchester

Watson Adventures

8 am – 5 pm

Watson Adventures’ Murder at the Met Scavenger Hunt

The Metropolitan Museum of Art

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