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26 Great Summer Festivals and Fairs in Westchester in 2025

Join Peekskill Pride for its annual Family Pride celebration in Pugsley Park. Photo courtesy of the event
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5/16/25 - By Katherine Dhurandhar

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

Summer Fairs and Festivals in Westchester in June 2025

Tarrytown Craft, Food, and Street Fair

Tarrytown–FREE
Sunday, June 1, 2025
Stroll Tarrytown's Main Street and discover more than 100 arts and crafts vendors, local shops and restaurants, live music, tasty food, face painting, a cartoonist, performances by Witches Along the Hudson, and more! Bring the whole crew—even your furry friends are welcome! READ MORE

Croton-on-Hudson Summerfest

Croton-on-Hudson–FREE
Sunday, June 1, 2025
The Village of Croton-on-Hudson hosts its 37th annual Summerfest street fair filled with live music, entertainment, delicious food, and more than 100 street vendors. READ MORE

Westchester Pride

White Plains–FREE
Sunday, June 1, 2025
Westchester Pride is the premier Pride celebration of Westchester County, welcoming thousands for a day filled with joy, empowerment, and connection. This free, family-friendly event features a full lineup of performances, activities, and resources for all ages in the heart of downtown White Plains. READ MORE

Armonk Fol-de-Rol Country Fair

Armonk
Thursday, June 5-Sunday, June 8, 2025
Excited happy faces, great music, terrific food, beautiful crafts, exciting rides, and games are all part of the Armonk Lions Club’s 49th Annual Fol de Rol Fair and Market in the Park. The Fol de Rol is Armonk’s treasured pre-summer ritual, providing fun for people of all ages. READ MORE

Festa Italiana in West Harrison

Harrison–FREE
Friday, June 6-Sunday, June 8, 2025
Celebrate Italian heritage all weekend long at Saint Anthony of Padua Church's annual festival. Enjoy Italian food, children's activities, games, and more.  READ MORE

Yonkers Greek Food Festival

Yonkers
Friday, June 6-Sunday, June 8, 2025
This three-day festival celebrating Greek culture includes food, live Greek music, folk dancing, a kids' zone, games, and more. The fun at this fest extends well past bedtime! Bring your appetite. READ MORE

Westchester Annual Strawberry Festival

Chappaqua–FREE
Saturday, June 7, 2025
The Church of St. Mary the Virgin Chappaqua's 88th Annual Strawberry Festival features games, live music, a bounce castle, a petting zoo, a slime bar,  strawberry shortcake, vendors, and more.  READ MORE

Hastings-on-Hudson Friday Night Pride

Hastings-on-Hudson–FREE
Friday, June 13, 2025
The community of Hastings is coming together to celebrate Pride with a march, live concert, and tons of family-friendly activities, including a giant rainbow slide, face painting, spray paint art, kids’ craft activities, dancing, community quiltmaking, a scavenger hunt, temporary tattoos, and games. READ MORE

Yonkers Ukrainian Heritage Festival

Yonkers–FREE
Friday, June 13-Sunday, June 15, 2025
Sponsored by the Ukrainian American Youth Association, this annual tradition brings Ukrainian food, culture, music, dancing, crafts, and traditions to Yonkers, along with carnival rides and games, plus assorted vendors.  READ MORE

Hudson River Music Festival

Croton-on-Hudson
Saturday, June 14, 2025
Families, children, and music lovers are invited to celebrate Father’s Day weekend with an unforgettable day of fun and inspiration at the Hudson River Music Festival at Croton Point Park. Family offerings include performances by the Rock and Roll Playhouse, Arm-of-the-Sea puppet shows, stories, songs, art workshops, and more.  READ MORE

Celebrate Juneteenth at Caramoor

Katonah–FREE
Sunday, June 15, 2025
Caramoor presents an uplifting Juneteenth celebration—honoring African American freedom, heritage, and resilience—with the electrifying sounds of The Legendary Ingramettes, one of gospel music’s most revered groups.   READ MORE

Puerto Rican Festival and Carnival

White Plains–FREE
Sunday, June 22, 2025
Celebrate Puerto Rican culture with live bomba drumming and dance with Grupo Cimarrones, performances by the Carlos Jimenez Mambo Orchestra, arts & craft vendors, as well as a procession led by the beloved and colorful vejigante, a folkloric character associated with Puerto Rican carnival. READ MORE

African-American Heritage Celebration at Kensico Dam

Valhalla–FREE
Sunday, June 22, 2025
Celebrate African-American culture at Kensico Dam Plaza. Enjoy live music, food, dance, drama, poetry, and a wide array of vendors. Bring a blanket or folding chairs and enjoy performances on the lawn.  READ MORE

American Roots Music Festival at Caramoor

Katonah
Saturday, June 28, 2025
Caramoor’s annual American Roots Music Festival fills the stunning grounds with the sounds of blues, Americana, folk, bluegrass, and more! Wander from stage to stage and discover your next favorite artist as an incredible lineup of bands brings the music to life in the picturesque venues.  READ MORE

Peekskill Pride in Pugsley Park

Peekskill–FREE
Saturday, June 28, 2025
Join Peekskill Pride for its annual Family Pride in Pugsley Park, with live bands, drag shows, and family-friendly activities including arts & crafts and drag queen storytime.  READ MORE
Groove to the Caramoor Jazz Festival. Photo courtesy of Caramoor
Groove to the Caramoor Jazz Festival. Photo courtesy of Caramoor

Westchester Summer Fairs and Festivals in July 2025

Mamaroneck Fireworks Spectacular and Fireman's Carnival

Mamaroneck–FREE
Thursday, June 26-Saturday, July 5, 2025
Enjoy 10 days of festivities at the Mamaroneck Fire Department's Carnival, featuring a parade, classic carnival rides, and a dazzling fireworks finale in Harbor Island Park. The St. Thomas Orchestra plays a free concert to accompany the fireworks display.  READ MORE

Music Fest and Fireworks at Kensico Dam

Valhalla–FREE
July 3, 2025
Start the Independence Day celebration a day early with entertainment, music, and fireworks in Kensico Dam Park. Enjoy eats from local vendors who set up a food court on-site. A kids' zone features a kids' DJ, inflatables, and kids' concessions. READ MORE

Pleasantville Music Festival

Pleasantville
Saturday, July 12, 2025
This festival combines the feel of a small-town, outdoor concert with nationally recognized musicians. There’ll be vendors, food, and fun stuff for kids like bouncy houses and a rock wall. Plus, you can catch nine hours of live music across three different stages. READ MORE

Hispanic Heritage Celebration at Kensico Dam

Valhalla–FREE
Sunday, July 13, 2025
Celebrate Hispanic culture at Kensico Dam Plaza. Bring your blankets and chairs and enjoy a day of live music, food, vendors, and more. READ MORE

Sleepy Hollow Mermaid Festival & Parade

Sleepy Hollow–FREE
Saturday, July 19, 2025
The Hudson River mermaids are back for another Sleepy Hollow Mermaid Festival! The fun begins with a parade on land and water, followed by a post-parade party in the park for all ages, with music, community art-making, face painting, food trucks, and bounce houses. READ MORE

Arab-American Heritage Celebration at Ridge Road Park

Hartsdale–FREE
Sunday, July 20, 2025
Celebrate Arab-American culture with live music, traditional dance performances, food, and vendors at Ridge Road Park in Hartsdale.  READ MORE

Caramoor Jazz Festival

Katonah
Saturday, July 26, 2025
Caramoor joins forces with Jazz at Lincoln Center to provide a day full of live music on its bucolic grounds. Pack a picnic or purchase food on-site, and stroll the lovely gardens.  READ MORE

Summer Fairs and Festivals in Westchester in August 2025

Heritage of India Festival at Kensico Dam

Valhalla–FREE
Sunday, August 3, 2025
Enjoy traditional Indian dance performances, music, food, vendors, and more at this celebration of the culture of India.  READ MORE

Whimsical Water Day at Sarah Lawrence

Yonkers
Saturday, August 9, 2025
Families are invited to learn about water quality in the community, go fishing with a seine net, play games, and win prizes at Sarah Lawrence College Center for the Urban River at Beczak. Enjoy free food and music. READ MORE

Katonah Classic Stage Film Festival

Bedford
Sunday, August 10, 2025
The Katonah Classic Stage partners with the Bedford Playhouse to celebrate and uplift stories on film. Films are presented outdoors under the stars and indoors in a state-of-the-art cinema. The program features young up-and-coming filmmakers and is a family-friendly day for those who love cinema. READ MORE

Jewish Music & Arts Heritage Festival at Kensico Dam

Valhalla–FREE
Sunday, August 17, 2025
Celebrate Jewish culture at Kensico Dam Plaza at the annual Jewish Music and Arts Festival. Bring your blankets and chairs and enjoy a day of music, Israeli dancing, food, vendors, and children's activities, including free face painting, juggling by Ned Gelfars, a WonderSpark puppet show, and more. READ MORE

Dia de la Cultura Ecuatoriana - Westchester Roots Festival

Sleepy Hollow–FREE
Sunday, August 17, 2025
Join Westchester Roots for an afternoon of Ecuadorian music, dance, food, and crafts, along with family-friendly presentations that feature traditional Ecuadorian costumes and the indigenous Kichwa language. READ MORE

Muslim Heritage Celebration at Kensico Dam

Valhalla–FREE
Sunday, August 24, 2025
Explore Muslim culture through exhibits, performances, and food. READ MORE

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

About the Author

Katherine Dhurandhar
Katherine Dhurandhar is a Community Publisher for Mommy Poppins, representing the Westchester and Hudson Valley region of New York, and a freelance copyeditor for Westchester Publishing Company. In her free time, she enjoys hiking, camping, and traveling with her husband and son.
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