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Best Things To Do in Westchester and the Hudson Valley May 2025 with Kids

Search the grounds of Locust Grove in Poughkeepsie for enchanted fairy houses. Photo courtesy of Locust Grove
Search the grounds of Locust Grove in Poughkeepsie for enchanted fairy houses. Photo courtesy of Locust Grove
4/28/24 - By Katherine Dhurandhar

From Mother's Day to Memorial Day, we've rounded up fun things to do all month long in Westchester and the Hudson Valley!

This May, enjoy treasure hunting, sword-fighting demonstrations, mermaids, and more at the annual Hudson Valley Pirate Festival at the Ulster County Fairgrounds. Or, check out an outdoor celebration of the Holi Festival of Colors in Hawthorne's Broadway Field Park, featuring bounce houses, Bollywood dancing, color throwing, and more.

Kids of all ages are invited to don their best fairy wings and join the annual Fairy House Hunt in the Garden at Locust Grove in Poughkeepsie's Locust Grove Estate every weekend in May.

These are just a few of our favorite things to do in Westchester and the Hudson Valley this May—we're adding more events to the Westchester Events Calendar every day. 

More Things To Do in Westchester and the Hudson Valley:

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Best Things To Do in Westchester and the Hudson Valley with Kids this May

Fairy House Hunt in the Garden at Locust Grove

Poughkeepsie
Weekends from Saturday, May 3-Sunday, June 22, 2025
Don your best wings and search the nooks and crannies of the Locust Grove grounds to find hidden fairy and gnome houses on an enchanted walk. Each fairy house celebrates a different heirloom flower or historic tree that grows on the gorgeous property. READ MORE

"Beetlejuice Jr." at the Irvington Theater

Irvington
Friday-Sunday, May 2-4, 2025
“It’s showtime!” The ghost-with-the-most comes to the Irvington Theater stage in this frightfully funny musical based on the beloved motion picture turned Broadway phenomenon. Don’t miss this wacky theatrical party for the entire family — starring Broadway Training Center’s cast of student performers. READ MORE

Peekskill Cherry Blossom Festival at Riverfront Green Park

Peekskill–FREE
Saturday, May 3, 2025
Celebrate the annual cherry blossom season at Riverfront Green Park in Peekskill, with guided tours of the blossoming trees, food vendors, live music, children's activities, a plant sale, and more.  READ MORE

I Love My Park Day

Multiple Locations–FREE
Saturday, May 3, 2025
The first weekend in May is the statewide "I Love My Park Day," when volunteers throughout New York step up to help clean and beautify state parks, beaches, and historic sites. Tasks could include gardening, removal of invasive vines or weeds, general cleanup, and more.  READ MORE

Musical May: A Children's Book Week Party at the New Rochelle Public Library

New Rochelle–FREE
Saturday, May 3, 2025
Get into the groove at the New Rochelle Library's music-themed celebration in honor of Children’s Book Week with special guests and activities that are sure to inspire a love of literacy and libraries. The afternoon includes and award-winning picture book author Jyoti Rajan Gopal sharing her book One Sweet Song, an ode to the power of music and community, a meet & greet with Pete the Cat, and make & shake tambourines. READ MORE

White Plains Comic Fest

White Plains–FREE
Saturday, May 3, 2025
This annual event organized by the White Plains Cares Coalition returns to a new location at the White Plains City Center, offering cosplay, video-game tournaments, face painting, superhero button-making, comic-strip design, panel discussions, digital-animation workshops, photo-ops, and a raffle. READ MORE

Arts Westchester Family ArtsBash

White Plains
Saturday, May 3, 2025
Enjoy a day of creativity and fun at Family ArtsBash! Kids can participate in hands-on arts workshops like felt flower-making and clay creations, enjoy a visit from the ArtsMobile, get their faces painted, be mesmerized by a theatrical show, and more. READ MORE

Mother’s Day Tea Party at Shake it Off

Scarsdale
Saturday, May 3, 2025
Bring mom for a fun and exciting Mother’s Day Tea party at Shake it Off. Kids will enjoy a tea party, vase painting, cupcake decorating, bracelet making, and a dance session with a Princess. READ MORE

"Don't Let the Pigeon Drive the Bus" at Emelin Theatre

Mamaroneck
Saturday, May 3, 2025
Don’t Let the Pigeon Drive the Bus! The Musical! is based on the Caldecott Honor award-winning “Pigeon” picture books by Mo Willems. It’s not easy being the Pigeon – you never get to do ANYTHING! But when the Bus Driver has a crisis that threatens to make her passengers (gasp!) late, maybe that wily bird CAN do something. READ MORE

KMA Family Day: Art and Alchemy

Katonah
Sunday, May 4, 2025
Featured artist Ali Banisadr joins Family Day at the Katonah Museum of Art for a day of discovery where scientific exploration and artistic creativity collide. Take part in large-scale painting experiments, artist-led demonstrations, mixed-media sculptures, a family tour, and more. READ MORE

Westchester Bicycle Sundays

Various locations–FREE
Kicks off Sunday, May 4, 2025
Cyclists, joggers, walkers, in-line skaters, and scooters can take to the open road on Sundays when the Bronx River Parkway is closed to motorized vehicles for a 13.1-mile stretch from Main Street in White Plains to Scarsdale Road in Yonkers.  READ MORE

Kids Fishing Day at Hudson Highlands Nature Museum

Cornwall
Sunday, May 4, 2025
Children will learn the skills of fishing or enhance their abilities to land a whopper! There will be a short lesson on fish anatomy, plus safe and proper casting/ landing techniques. The Hudson Highlands Nature Center will provide the bait. A rod taller than your child with a push-button reel is recommended. READ MORE

Pinkster Festival at Philipse Manor Hall

Yonkers–FREE
Saturday, May 10, 2025
Celebrate Pinkster, an Afro-Dutch celebration of a week of temporary freedom for enslaved people, with African music and dance, games, and children’s activities, vendors, and food and drink.  READ MORE

Mad Hatters' Parade in Hudson

Hudson–FREE
Saturday, May 10, 2025
Prepare for the whimsical, the wacky, and the wow at this absurdist parade featuring artisan-made attire and accoutrements. Don your own handmade craft and march along or spectate from the sidelines. READ MORE

Albany Tulip Festival in Washington Park

Albany–FREE
Saturday & Sunday, May 10 & May 11, 2025
Albany's Dutch heritage is celebrated with a craft fair, a fine-art show, food, a KidZone, live entertainment on two stages, and more than 140,000 tulips in 150 different varieties in Washington Park. Time your visit for Dutch street scrubbing, tulip tours, and the tulip-queen coronation. READ MORE

Hudson Valley Pirate Festival at the Ulster County Fairgrounds

New Paltz
Saturday & Sunday, May 10 & 11, 2025
The Hudson Valley Pirate Festival is a two-day family-friendly festival at the Ulster County Fairgrounds celebrating everything about pirates: sword fighting, singing, dancing, and, of course, treasure hunting. Highlights include a pirate ship and a pirate encampment, mermaids, a psychic, a photo booth, and lots of games and activities for children. READ MORE

Sheep Shearing Festival at Muscoot Farm

Katonah–FREE
Sunday, May 11, 2025
Drop in to watch the annual shearing of Muscoot Farm's resident sheep and learn why it's done. This event also features vendors and activities and is held rain or shine. READ MORE

Holi Festival of Colors in Broadway Field Park

Hawthorne
Saturday, May 17, 2025
Join Shake it Off and Mayura Dance Academy at the Holi Festival of Colors in Broadway Field Park in Hawthorne. What is Holi?  Holi, the Hindu festival of colors, is a holiday characterized by joy, color, and the celebration of new beginnings. Enjoy good food, bounce houses, music, and more! Dress all in white for the throwing of colors. READ MORE

Yonkers Arts Weekend (YAW) at Hudson River Museum

Yonkers–FREE
Saturday, May 17, 2025
Enjoy free admission to the Hudson River Museum and family-friendly activities, including art workshops that celebrate our current exhibitions, the environment, and the thriving arts scene in Yonkers. Participate in a “Bubble Extravaganza” with giant bubbles, flowing streamers, and kites in the courtyard, and hear live music from Westchester Center for Jazz Ensemble.  READ MORE

Hudson Valley Kite Fest

Kingston–FREE
Saturday, May 17, 2025
Get ready to soar at Kingston’s 2nd Annual Hudson Valley Kite Fest! Whether you’re a seasoned flyer or a first-timer, this free, family-friendly event is the perfect place to experience the joy of kites. Bring your own or purchase and design one on-site—then watch it take flight over Kingston Point Beach!  READ MORE

Maker Weekend at the Westchester Children's Museum

Rye
Saturday & Sunday, May 17 & 18, 2025
 Join the Westchester Children's Museum for Magnetic Motion, Robo Menagerie, Cardboard Bridges, Kinetic Balance Sculptures, Math Marble Machines, and Hot Glue 101.  READ MORE

Sheep and Wool Festival in Chestnut Ridge

Chestnut Ridge–FREE
Sunday, May 18, 2025
Held under leafy shade trees at the Threefold Community Campus in Chestnut Ridge, this family-oriented community event features child-friendly craft activities, a petting zoo & pony rides, live music, local craft vendors, and delicious food. READ MORE

Mayfest Farmers and Makers Market at Walkway Over the Hudson

Highland–FREE
Saturday, May 24-Monday, May 26, 2025
More than 180 vendors offer food and crafts, plus families can enjoy a full day of live music and specialty performances, art installations, and kids' games and activities at Poughkeepsie's Walkway Over the Hudson. READ MORE

Woodstock-New Paltz Art & Crafts Fair at Ulster County Fairgrounds

New Paltz
Saturday, May 24-Monday, May 26, 2024
Held twice yearly—Memorial Day and Labor Day weekends—this fair showcases the work of more than 200 artists from across the United States at the Ulster County Fairgrounds. The children's tent features demonstrations and supervised arts and crafts projects. Live entertainment and activities are planned. READ MORE

Places featured in this article:

Philipse Manor Hall State Historic Site
Walkway Over the Hudson - Ulster Welcome Center Plaza

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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