Prepare for the whimsical, the wacky, and the wow-worthy at the Mad Hatters' Parade. Photo courtesy of Processional Arts
Prepare for the whimsical, the wacky, and the wow-worthy at the Mad Hatters' Parade. Photo courtesy of Processional Arts

Awesome Things To Do in Westchester in May With Kids: Spring Fests, Circus, and More

In May 2020, Westchester and the Hudson Valley were essentially shut down, but fast-forward a year and our calendar is bursting with activity for area families. We’re excited that everything is slowly opening back up and thrilled to have so much fun stuff to shout about.

From spring fairs and festivals to the zany Mad Hatters' Parade and the return of the beloved Bicycle Sundays, the family-friendly fun is happening all month long. You might be surprised by how many of our favorite events are FREE. You’ll also find a lot more inspiration in our Spring Fun Guide and our Event Calendar, which keeps on growing.

Read on for the May events that are making us smile—and if you haven’t yet chosen a summer camp, we have many resources to guide you, including the Mommy Poppins Online Camp Fair.

Editor's note: While we are trying to promote safer activities that occur outdoors or with social distancing guidelines in place, please keep your family and others safe by always wearing a mask and practicing social distancing. If you arrive at an event that appears too crowded, try using the “nearby” search feature on our Event Calendar to find something else to do. Some photos in this post were taken before the pandemic.

Places featured in this article:


Staatsburgh State Historic Site
upcoming events

Bedford Hills Train Station

Katonah Museum of Art
upcoming events
(Sat May 15, 2021) KMA Family Day

Kaatsbaan
upcoming events
(Thu May 20, 2021 - Sun May 30, 2021) Kaatsbaan Spring Festival

Greenburgh Nature Canter
upcoming events

Museum Village
upcoming events
(Fri May 28, 2021 - Mon May 31, 2021) Zerbini Family Circus

Ulster County Fairgrounds
upcoming events
(Sat May 29, 2021 - Mon Sep 6, 2021) Woodstock-New Paltz Art & Crafts Fair
Neighborhood Guides
Activity Guides