26 Great Summer Festivals and Fairs in 2025 in Westchester

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:
OUR LATEST VIDEOS
Places featured in this article:
Upper Village of Croton-on-Hudson
Downtown White Plains
Wampus Brook Park
St. Michael’s Ukrainian Catholic Church
Caramoor Center for Music and the Arts
Renaissance Plaza
Kensico Dam Plaza
Caramoor Center for Music and the Arts
Pugsley Park
Harbor Island Park
Parkway Field
Kensico Dam Plaza
Kingsland Point Park
Ridge Road Park
Kensico Dam Plaza
Sarah Lawrence College Center for the Urban River at Beczak
Kensico Dam Plaza
Barnhart Park
Kensico Dam Plaza