There's just one weekend left to enjoy all the medieval fun at the New York Renaissance Faire. Photo courtesy of the faire
There's just one weekend left to enjoy all the medieval fun at the New York Renaissance Faire. Photo courtesy of the faire

Best Things To Do in Westchester in October 2021 with Kids

October is loaded with Halloween and fall fun, and there's no shortage of either in Westchester and the Hudson Valley! We recently posted our guide to the best Halloween events in in the area, which includes the return of beloved annual traditions, including the Great Jack O'Lantern Blaze; this list alone could serve as our “best of October” roundup, but not all October highlights owe to ghosts and goblins.

The lineup of fall festivals is stellar, and two children’s book festivals offer author encounters and other appeal for young bibliophiles. One of our favorite carnivals is back, as is indoor children's theater. Adding to all this are numerous destinations for apple and pumpkin picking, and much fun is to be had navigating area corn mazes.

Now, read on for our favorite October things to do, but give equal attention to our list of best Halloween events, as there are many more standout events in that guide. Be prepared for sellout situations by snagging your tickets early. 

Even more opportunities await on our activities calendar, with more added frequently.

Places featured in this article:


Robert E. Bell Middle School

The CENTER for Performing Arts at Rhinebeck

Headless Horseman Hayrides and Haunted Houses

Bethel Woods Center for the Arts

Beacon Sloop Club and Riverfront Park

Chappaqua Train Station Parking Lot

Caramoor Center for Music and the Arts

Headless Horseman Hayrides and Haunted Houses
Home of the 'Legend'
Washington Irving's Sunnyside - 10:00 AM Pick
Soukup Farms Harvest Festival
Soukup Farms - 11:00 AM Pick
1860s Family Fun Day
Horace Greeley House - 11:00 AM Pick
Peace, Love & Pumpkins
Bethel Woods Center for the Arts - 6:30 PM Pick
Neighborhood Guides
Activity Guides