May GoList: Best Things to Do in Westchester with Kids

Things to Do

May is a lively month in Westchester and the Hudson Valley, with events honoring Mother’s Day, Memorial Day and spring. Below we've rounded up our top picks; limiting them was no easy task. Beyond the diversity and novelty that these events offer, many happen to also be free!

Making its debut this year is the all-new Valley Con, a festival for lovers of comics, cosplay and gaming. Playland turns 90 years young, and with this milestone comes a bash, of course. Numerous annual traditions return, such as the UFO Fair, the zaniest of the many Hudson Valley spring festivals we’ve rounded up. Kid-bop icon Laurie Berkner returns to the stage, so snag those seats and Velcro those dancing shoes; and while you’re buying tickets, book your slide down the rabbit hole to the new Tilly's Tea with Alice.

Of course, the main event of May is Mother’s Day, and we’ve rounded up both where to go for Mother’s Day brunch and 35 alternatives (or supplements) to the family meal. And be sure to indulge in assorted Star Wars-themed activities at any of the many events called May the 4th Be With You (get it?).

Read on for the rest of our lowdown. If you're looking for even more options (and trust us, there are many), check out our Event Calendar and sign up for our free newsletters to stay in the know!

Tilly's Tea with Alice: A Curious Adventure Through Wonderland – Brewster
Thirteen dates starting May 4, 2018
We’ve seen many popular children’s stories adapted to the stage; at this production, the literature is transformed into a walk-through, multi-faceted, interactive exhibit/performance. Tickets are likely to go fast. Curious? Read our inside scoop.

Hudson Valley Fair - Fishkill
Fridays, Saturdays and Sundays, May 4-20, 2018
Nothing says “spring” like a traditional county fair! This one offers carnival rides, shows and a petting zoo, plus fireworks on Saturday nights to boot. The entertainment is out of the ordinary—a Banana Derby (monkeys riding dogs), hypnotists and lions and tigers. Also consult our guide to other spring festivals in the Hudson Valley.

I Love My Park Day - Various Locations
Saturday, May 5, 2018
Want to give back to your community while enjoying the fresh air? More than just cleaning up, the tasks in need of volunteers include planting, construction, habitat repair and more. A statewide effort, participating sites include locations in Westchester and the Hudson Valley. Free

Hudson Valley Cupcake Festival - Beacon
Saturday, May 5, 2018
Is four hours enough time to browse, assess and consume some of the 20,000 cupcakes available and take in an inflatable slide and bouncy castle? If you feel more time is needed, there's a similar event later this month: Gardiner Cupcake Festival.

Valley Con – Yorktown Heights
Saturday, May 5, and Sunday, May 6, 2018
This new event offers a robust list of attractions for fans of gaming, comics, cosplay and more—all of which is free. Highlights include video game tournaments, celebrity encounters, screenings, vendors and more.

Yonkers Arts Weekend - Yonkers
Saturday, May 5, and Sunday, May 6, 2018
This weekend-long celebration of the arts is held at multiple venue and includes free workshops, performances and artist meet-and-greets. Among the attractions is the annual Kite Festival. All events are free.


Sing and dance along with preschool fave Laurie Berkner. Image credit: Jayme Thornton

Laurie Berkner - Peekskill
Saturday, May 12, 2018
Popular children’s performer Laurie Berkner, who rose to national fame on the TV program Jack's Big Music Show, will rock her bubbly kid music on the Westchester stage. Bring your dancing shoes!

White Plains Comic Fest – White Plains
Saturday, May 12, 2018
Come dressed up as your favorite character and prepare for video-game tournaments, face painting, superhero button-making, comic-strip design, special guest appearances, toy vendors, comic-book artists, digital-animation workshops, photo ops and a raffle. Most of this is free.

10th Anniversary Science Barge Opening - Yonkers
Saturday, May 12, 2018
The Science Barge will kick off the 2018 season with a bash to celebrate its 10th year of educating and stimulating Westchester families. The afternoon will feature live performances, museum theater, on-shore games, kite flying, live animals, robotics, food trucks, giant puppets, science experiments and more—all free.


And you thought teaching your dog to sit was a feat! Photo of the Stunt Dog Experience courtesy of the production.

The Stunt Dog Experience - Peekskill
Sunday, May 13, 2018
This stunt act is really for the dogs! Get ready for exciting tricks, big air stunts, comedic antics, dancing and athletic feats, as seen on TV!

St. Patrick's Annual Carnival – Bedford
Tuesday, May 15 - Sunday, May 20, 2018
Carnival season returns with this six-day fair featuring rides, food and other fun.

Family Arts Bash – White Plains
Saturday, May 19, 2018
Block out the afternoon for an assortment of performances and hands-on art workshops that include hat-making, building with clay, drawing with both hands and more.


The UFO Fair is truly out of this world! Photo courtesy of the Town of Crawford.

UFO Fair – Pine Bush
Saturday, May 19, 2018
Intergalactic fun awaits at this amusing annual tradition. The village reportedly has a history of UFO sightings and has taken to celebrating this distinction with the yearly fest. Family-friendly activities are included, such as an Alien Parade (costumes encouraged!), live music, pop-up performances, games, food, roaming characters and more. With any luck you just might meet an alien!

Celebrate Pinkster – Sleepy Hollow
Saturday, May 19, 2018
This festival features performances of African drumming and dancing, instruction, traditional storytelling, cooking demos and historical presentations. Kids craft their own djembe to take home.


The Grand Carousel is one of Playland's remaining artifacts from the 1920s. Photo credit: Susan Miele for Mommy Poppins

Playland's 90th Birthday - Rye
Saturday, May 26, 2018
Some things have changed, but not the fun. A family attraction since 1928, Playland is throwing itself a 90th birthday party, and your family is invited! Enjoy discounted rides admission, cake, a prize wheel and a raffle for a chance to win a season pass. Entertainment throughout the day includes a magic show, a DJ, strolling period costumers, vintage cars, a clown and a juggler.

Annual Memorial Day Races & Fair - South Salem
Monday, May 28, 2018
The 42nd annual fair is preceded by a fun run (adult and kid races), and includes a craft fair, bake sale, games, entertainment and more.

ICS Carnival - Tuckahoe
Thursday, May 31–Sunday, June 3, 2018
All ages will enjoy this annual full-fledged carnival, which features both kiddie rides and rides for older kids, bumper cars, food stands and more. Read our review of this event.

Be sure to check our Event Calendar for even more fun happening throughout Westchester!

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