26 Great Summer Festivals and Fairs in 2025 in Westchester

Play under the balloons at the Hudson Valley Hot Air Balloon Festival. Photo courtesy of the festival
Play under the balloons at the Hudson Valley Hot Air Balloon Festival. Photo courtesy of the festival
5/17/24 - By Susan Miele

Summer fairs and festivals in Westchester offer a ton of ways to party al fresco from June through August. Westchester's staged outdoor entertainment options include picnic-blanket music festivals and cultural-heritage feasts.

Kick off the summer festivities at the Westchester Annual Strawberry Festival in Chappaqua, featuring live music, a petting zoo, and the famous strawberry shortcake. Other stand-out events include the return of the Sleepy Hollow Mermaid Festival and a 4th of July celebration at Mamaroneck's Fireworks Spectacular and Fireman's Carnival in Harbor Island Park.

Families can also celebrate Pride Month at multiple kid-friendly celebrations, including Hastings-on-Hudson Friday Night Pride, which features a parade, concert, and tons of kids' activities, such as a giant rainbow slide and face painting.

Looking for even more family-friendly activities? Consult our Event Calendar and Summer Fun Guide, and sign up for our newsletters to get posts like this delivered to your inbox.

More Free Activities in the Hudson Valley this Summer:

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Places featured in this article:


Caramoor Center for Music and the Arts

Caramoor Center for Music and the Arts

Caramoor Center for Music and the Arts

Sarah Lawrence College Center for the Urban River at Beczak