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Best Free and Fun Things To Do in Westchester and the Hudson Valley with Kids May 2024

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!

Family-friendly fun is happening all month long in Westchester and the Hudson Valley. Standout events include a celebration of the Hindu festival Holi Festival of Colors in Hawthorne, the Hudson Valley Pirate Festival at the Ulster County Fairgrounds, and the start of the annual Fairy House Hunt in the Garden at Locust Grove in Poughkeepsie.

Find more top May picks in our Guide to Spring Activities and get all our top picks in your inbox when you sign up for our newsletters.

 

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

Peekskill Cherry Blossom Festival at Riverfront Green Park

Peekskill–FREE
Saturday, May 4, 2024
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

Fairy House Hunt in the Garden at Locust Grove

Poughkeepsie
Weekends from Saturday, May 4-Sunday, June 30, 2024
Don your best wings and search the nooks and crannies of the Locust Grove grounds to find 30 hidden fairy houses on an enchanted walk. Each fairy house celebrates a different heirloom flower or historic tree that grows on the gorgeous property. READ MORE

KMA Family Day: Symbols, Stories, and Self

Katonah
Saturday, May 4, 2024
Join artist Damien Davis, whose work is featured in The Pollack Family Learning Center, for a collaborative kinetic sculpture project bursting with vibrant colors and magical moving parts. Creative activities will be happening all around the Katonah Museum of Art, including decorating rocket ships, astronaut buttons, a cozy story corner, and more.  READ MORE

Holi Festival of Colors in Broadway Field Park

Hawthorne
Saturday, May 4, 2024
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)

Yonkers–FREE
Saturday & Sunday, May 4 & 5, 2024
The 10th annual Yonkers Arts Weekend (YAW) festival is held at multiple locations in Yonkers. The two-day festival is filled with exciting programs, workshops, exhibitions, and much more. Workshops for kids include children's art workshops at Blue Door Art Center, We Art One, and the Hudson River Museum.  READ MORE

Sugar Loaf Spring Festival

Sugar Loaf–FREE
Saturday & Sunday, May 4 & 5, 2024
Sugar Loaf's spring festival is set for a day of open-air fun. Join vendors throughout the village–including local shops, galleries, and restaurants–as they set up their wares and eats in tents for visitors to peruse. READ MORE

Fiesta Musical for Cinco de Mayo at the New Rochelle Public Library

New Rochelle–FREE
Sunday, May 5, 2024
Celebrate Cinco de Mayo at the New Rochelle Public Library. This hour-long program for families brings together dazzling music by US and Mexican composers -- including Aaron Copland, Leonard Bernstein, Arturo Marquez, Juan Pablo Contreras, Carlos Chavez, and more. READ MORE

Westchester Bicycle Sundays

Various locations–FREE
Kicks off Sunday, May 5, 2024
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

I Love My Park Day

Multiple Locations–FREE
Saturday, May 6, 2023
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

White Plains Comic Fest

White Plains–FREE
Saturday, May 11, 2024
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

Children's Book Week Party at the New Rochelle Public Library

New Rochelle–FREE
Saturday, May 11, 2024
Celebrate Children’s Book Week at the New Rochelle Public Library with a slew of special guests and treats that will inspire a love of literacy and libraries. The afternoon includes award-winning author and illustrator James Yang, creator of such celebrated picture books as A Boy Named Isamu & Stop! Bot!, a meet-and-greet with Mo Willems’ superstar Pigeon, and cookie decorating. READ MORE

2024 Family ArtsBash at ArtsWestchester

White Plains
Saturday, May 11, 2024
Enjoy a day of arts and fun at Family ArtsBash! Kids can participate in hands-on creative workshops like felt flower-making and clay creations, enjoy a visit from the ArtsMobile, get their face painted, be mesmerized by a puppet show, and more throughout ArtsWestchester’s landmark building in White Plains. READ MORE

Pinkster Festival at Philipse Manor Hall

Yonkers–FREE
Saturday, May 11, 2024
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. Celebrate spring while learning about this cultural history at Philipse Manor Hall.  READ MORE

Mother’s Day Tea Party at Shake it Off

Scarsdale
Saturday, May 11, 2024
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

Albany Tulip Festival in Washington Park

Albany–FREE
Saturday & Sunday, May 11 & May 12, 2024
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 11 & 12, 2024
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

Hudson Valley Cupcake Festival at Heritage Financial Park

Wappingers Falls–FREE Admission
Sunday, May 12, 2024
Enjoy a day of gourmet cupcakes, food trucks, gifts, and more at Heritage Financial Park in Fishkill...all to celebrate mom on Mother's Day! READ MORE

Sheep Shearing Festival at Muscoot Farm

Katonah–FREE
Sunday, May 12, 2024
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

"A Year with Frog & Toad" at The Play Group Theatre

White Plains
Sundays, May 12 & 19, 2024
Spring's almost here! Meet Frog and Toad, best friends, who hop, sing, and dance their way through a year of adventure with all their playful and quirky pals: Mouse, Turtle, Lizard, a crew of birds, and a whole bunch of friendly critters. From swimming, to sledding, to singing about cookies, these bright and memorable characters will jump right into your heart!  READ MORE

Mad Hatters' Parade in Hudson

Hudson–FREE
Saturday, May 13, 2023
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

"Peter & the Wolf & Other Excerpts" at the Chappaqua Performing Arts Center

Chappaqua
Saturday, May 17, 2024
"Peter and the Wolf and Other Excerpts" is a delightful one-hour program, well-suited for school-aged children and young families held at the Chappaqua Performing Arts Center. In addition to the beloved symphonic classic, Peter and the Wolf, the program includes three classical excerpts, all highlighting the talent and versatility of Westchester Ballet Company’s youth dancers.  READ MORE

Polish Heritage Celebration at Kensico Dam Plaza

White Plains–FREE
Sunday, May 19, 2024
Celebrate Polish culture at Kensico Dam Plaza. Bring your blankets and chairs and enjoy a day of live music, food, vendors and more. READ MORE

Sheep and Wool Festival in Chestnut Ridge

Chestnut Ridge–FREE
Sunday, May 19, 2024
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

Día de las Familias at the Ashokan Center

Olivebridge
Sunday, May 19, 2024
Día de las Familias is a new music and arts festival with music, food vendors, nature walks, activities for children, and more – todo en Español! This event will be held on the Ashokan Center campus in Olivebridge, NY and feature live music by renowned traditional Veracruz artists from the Ariles Son Jarocho Camp, and more Latin musicians to be announced. READ MORE

Laurie Berkner Greatest Hits Solo Show at the Paramount Hudson Valley Theater

Peekskill
Sunday, May 19, 2024
Award-winning children’s recording artist Laurie Berkner, made famous on TV’s Nick Jr. and Sprout channels, will perform new material at the Paramount Hudson Valley Theater. Berkner has also composed Off-Broadway children's musicals and inspired three picture books.  READ MORE

Mayfest Farmers and Makers Market at Walkway over the Hudson

Highland–FREE
Saturday, May 25-Monday, May 27, 2024
In addition to browsing food and crafts from more than 180 vendors, families can enjoy a full day of live music and specialty performances, art installations, and games and activities for kids at the Walkway over the Hudson in Poughkeepsie. READ MORE

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

New Paltz
Saturday, May 25-Monday, May 27, 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:

Yonkers Downtown Waterfront BID
Philipse Manor Hall State Historic Site
Chappaqua Performing Arts Center
Walkway Over the Hudson - Ulster Welcome Center Plaza