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Best Family Festivals and Street Fairs in NYC this May

Enjoy the May Fair to welcome spring's arrival at the New Amsterdam School. Photo courtesy of the school
Enjoy the May Fair to welcome spring's arrival at the New Amsterdam School. Photo courtesy of the school
5/4/25 - By Drew Kristofik

NYC street fairs and festivals are blooming all over this May, from glorious school fairs like Calhoun's carnival-fun-filled fest to the little-kid-friendly event at Columbia Greenhouse Nursery School. 

Plus, Hippo Playground hosts a Spring Fair complete with pony rides, Randall's Island's Touch-a-Truck Fest returns, there's a Mother's Day Garden Party at the NYBG, and the annual salute to service that is Fleet Week punctuates Memorial Day weekend. Plus, don't miss Mommy Poppins' Spring Fling on Car-Free Montague Street our our very first Family Travel Fest!

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Best Fairs and Festivals in NYC May 2025

Hippo Playground Spring Fair in Riverside Park

Upper West Side
Sunday, May 4, 2025
An Upper West Side institution, the Hippo Playground Spring Fair celebrates the season with pony rides, bouncy castles, a petting zoo, games, prizes, crafts, food, cupcake decorating, face painting, entertainment, and more. READ MORE

PS 267 Spring Fling

Upper East Side
Sunday, May 4, 2o25
East Side Elementary School PS 267 hosts its annual block party with a day of fun for the whole family. Enjoy bouncy houses, games, crafts, and snacks. Proceeds benefit the PS 267 PTA and the programs it supports. READ MORE

61st Annual Calhoun Spring Carnival

Upper West Side
Saturday, May 10, 2025
Carnival rides and games, prizes, and craft activities are trademarks of the annual celebration for the Calhoun community and neighborhood families. Enjoy the traditional first barbecue of the season with hot dogs, hamburgers, salads, freshly made sandwiches, and more. READ MORE

Urban Wildlife Festival in St. Mary's Park

South Bronx – FREE
Saturday, May 10, 2005
Get up close and personal with NYC’s wild residents. Learn about squirrels, turtles, raccoons, opossums, and coyotes, and discover the best places in New York City and New York state to watch wildlife. READ MORE

Show Brooklyn Some Love Fest at Albee Square

Downtown Brooklyn – FREE
Saturday, May 10, 2025
Brooklyn Org, Brooklyn Bridge Parents, Downtown Brooklyn Partnership and City Point unite for a hands-on floral experience just in time for Mother's Day! Pick your favorite stems from the fresh “Flower Bar,” then design your very own custom bouquet. Add your personal flair with rhinestones, pretty ribbons, and Mother's Day message!   READ MORE

Japan Day Parade and Street Fair on Central Park West

Upper West Side – FREE
Saturday, May 10, 2025
Japan Day is celebrated with a parade and street fair. Watch the parade march down Central Park West before enjoying the festive street fair along 72nd Street.  READ MORE

Bird Bonanza on Randall's Island

Randall's Island – FREE
Sunday, May 10, 2025
Celebrate birds, especially those that are currently migrating through NYC, at the Randall’s Island Bird Bonanza. The entire day is dedicated to flying feathered friends, with activities and games for all ages. READ MORE

Mother's Day Weekend Garden Party at NYBG

Bronx Park, the Bronx
Saturday, May 10-Sunday, May 11, 2025
Mother's Day at the New York Botanical Garden is abloom with activities, music, crafts, and face painting—not to mention walking tours packed with colors and gorgeous spring scents. READ MORE

Greek Jewish Festival

Lower East Side – FREE
Sunday, May 11, 2025
This Greek Jewish Festival celebrates the unique Romaniote and Sephardic heritage of the Jews of Greece. Enjoy a feast for the senses, including authentic kosher Greek foods and homemade Greek pastries. READ MORE

Apple Blossom Children's Carnival at the Queens County Farm Museum

Glen Oaks, Queens
Weekends through Sunday, May 11, 2025
Celebrate spring at the Queens County Farm Museum. This children's carnival kicks off the farm's special event season. Tilt-A-Whirl in the orchard and enjoy carnival rides, hayrides, and midway games. READ MORE

Kite Festival in Brooklyn Bridge Park

Brooklyn Bridge Park – FREE
Saturday, May 17, 2025
Brooklyn Bridge Park kicks off its spring and summer programming season with this beloved kite-flying fest. This family-friendly event takes over BBP's Pier 5, offering all ages the opportunity to watch their kites soar above the Manhattan skyline while enjoying special activities exploring the science of flight. READ MORE

Willowtown Spring Fair

Brooklyn Heights
Saturday, May 17, 2025
The Willowtown Association hosts its annual spring fair with face painters, a bouncy house, a bake sale, music, games, and more.  READ MORE

Big Truck Day on Randall's Island

Randall's Island – FREE
Saturday, May 17, 2025
Strap on your seatbelt and get a close-up view of the big trucks that keep New York City clean and safe. Learn how firefighters, garbage truck drivers, and other big truck operators use these vehicles to drive our city forward. READ MORE

Submerge: NYC Marine Science Festival at Pier 84

Midtown West – FREE
Saturday, May 17, 2025
Hudson River Park presents Submerge—a free science extravaganza devoted to raising awareness about our coastal waters. Celebrate local marine science through hands-on activities, catch-and-release fishing, science stage events, kayaking, and more!  READ MORE

Pinkster Celebration at Wyckoff Farmhouse Museum

Flatbush, Brooklyn – FREE
Saturday, May 17, 2025
The Wyckoff House Museum and Elite Learners join forces for a special Pinkster Festival with live music, carnival activities, drumming, and more. READ MORE

Spring Festival at Shoelace Park

Woodlawn Heights, the Bronx – FREE
Saturday, May 17, 2025
NYC Parks and Council Member Kevin Riley host a spring festival that includes games, arts and crafts, sports, and much more. READ MORE

Queens International Children's Festival at Rufus King Park

Jamaica, Queens – FREE
Saturday, May 17, 2025
JCAL's Queens International Children's Festival returns with high-quality arts performances and craft activities to inspire young people and families to enjoy the arts.  READ MORE

Forest Hills Youth Association's Spring Fling

Forest Hills, Queens
Saturday, May 17,2025
The FHYAA hosts its annual premier fundraising event, complete with bounce houses, face painting, glitter body art, live music, games, a pie-eating contest, chili cook-off, and more.   READ MORE

Family Fun Day at Hudson Yards

Midtown West – FREE
Saturday, May 17, 2025
Hudson Yards hosts an action-packed day of family-friendly entertainment, with music, magic, and interactive performances, including a high-energy western set by Hopalong Andrew, a special Resonant Minds concert by Mozart for Munchkins celebrating its latest book launch, and a magical show featuring a real (and very loved) rabbit! READ MORE

Dance Parade + DanceFest in the East Village

East Village – FREE
Saturday, May 17, 2025
Dance Parade returns to the streets, celebrating its 19th-annual procession and festival with 10,000 dancers and more than 100 unique styles of dance. READ MORE

Family Fun Day at Carl Schurz Park

Upper East Side – FREE
Saturday, May 17, 2025
NYC Parks and Council Member Julie Menin host a fun afternoon of crafts, music, jumbo games, the challenging Grit N’ Wit obstacle course, and more. READ MORE

May Fair at New Amsterdam School

Lower East Side
Saturday, May 17, 2025
May Fair welcomes the arrival of spring with Maypole dancing, vibrant flower crowns, puppet shows, international foods, baked goods, and more.   READ MORE

Ninth Avenue International Food Festival

Hell's Kitchen
Saturday, May 17-Sunday, May 18, 2025
Enjoy cuisines from different countries, including Poland, Italy, Spain, Greece, Japan, Thailand, and more. From open to close, visitors can browse the offerings along 15 city blocks of gourmet food and beverages. READ MORE

Sheep Shearing Festival at the Queens County Farm Museum

Glen Oaks, Queens
Sunday, May 18, 2025
Visit the Queens County Farm Museum on the Nassau-Queens border to see the sheep get their annual haircuts. Move to the foot-stomping rhythms of live music, and enjoy farmer-led tours and a plant sale all day.  READ MORE

The Fabulous Fifth Avenue Street Fair

Park Slope, Brooklyn
Sunday, May 18, 2025
Head to Park Slope's Fifth Avenue to peruse this street fair, featuring food and sale items, rides, bouncy castles, music performances, and more.  READ MORE

Emanu-El Downtown: 33 Jamboree at Chelsea Piers

Chelsea
Sunday, May 18, 2025
Celebrate community at a Lag B’Omer-inspired camp festival filled with sports, (phony) bonfires, and non-stop fun! Crowd around the campfire and hear songs from Shira and Rabbi Sarah, make s’mores, eat ice cream, and then run around playing all the sports (baseball, basketball, relay races, and more!)   READ MORE

Spring Fling on Car-Free Montague Street

Brooklyn Heights – FREE
Sunday, May 18, 2025
Mommy Poppins and Brooklyn Bridge Parents host their first Spring Fling during Open Streets on Montague, with 25 free kids' activities, a dance party, and a puppet show. Stop by for games, arts and crafts, soccer, face painting, building activities, an obstacle course, and much more.   READ MORE

Party on Wheels at the NY Transit Museum

Downtown Brooklyn
Sunday, May 18, 2025
The New York Transit Museum celebrates its Earth-friendly transit system at the Party on Wheels, its annual family benefit. Bring the whole family for breakfast and coffee, artmaking and face painting, a photo opportunity, a scavenger hunt, and unlimited rides on vintage subway cars from the museum platform to Hoyt-Schermerhorn and back.  READ MORE

Strawberry Festival at Brick Presbyterian Church

Upper East Side – FREE
Sunday, May 18, 2025
Don't miss the highly anticipated all-church picnic and strawberry festival on 92nd Street, featuring live music, scrumptious food, exciting kids' activities, and joyful conversations with friends and neighbors.  READ MORE

Fleet Week NYC

Hell's Kitchen – FREE
Wednesday, May 21-Monday, May 26, 2025
The US Navy, US Marine Corps, and US Coast Guard's celebration of sea services invites families to tour ships, watch the Parade of Ships, and enjoy exhibits, military band concerts, and aviation events throughout the week.   READ MORE

Lower East Side Festival of the Arts Street Fair

Lower East Side – FREE
Friday, May 23-Sunday, May 25, 2025
NYC's Lower East Side Festival of the Arts is a cabaret-style festival featuring more than 100 performing groups from the Lower East Side. This year's theme: We will not be silenced, speak up for democracy. READ MORE

NY Family Travel Fest, Presented by Dreams Resorts & Spas

Downtown Brooklyn – FREE
Saturday, May 31, 2025
Join Mommy Poppins for a fun-filled, travel-themed festival, including a world music dance party, fun cultural activities, and games and prizes, including the chance to win a birthday party at Dave & Buster's! Families can walk the red carpet and snap photos on the step & repeat and participate in a Masterchef Junior Mystery Box Challenge inspired by the hit competition show from our partner Dreams Resorts & Spas.  READ MORE

LIC Springs into Summer

Long Island City, Queens – FREE
Saturday, May 31, 2025
The Long Island City Partnership celebrates Long Island City with live music, dance, and performances, plus interactive lessons, art, fitness classes, outdoor dining, pop-up activities, games, and more. READ MORE

Family Fun Day in John Jay Park

Upper East Side – FREE
Saturday, May 31, 2025
NYC Parks and Council Member Julie Menin host a fun afternoon of crafts, inflatables, music, jumbo games, an obstacle course, and more READ MORE

14th Annual Bushwick Collective Block Party

Bushwick, Brooklyn
Saturday, May 31, 2025
Graffiti, street art, live music, food trucks, and local vendors converge to create an immersive experience that showcases the best of the community.   READ MORE

Places featured in this article:

Urban Farm at Randall's Island Park
Forest Hills Youth Athletic Association
Chelsea Piers Field House
Various locations

About the Author

Drew Kristofik
Drew Kristofik’s career took a twist from editing teen magazines to a seven-year stint at MacNeil/Lehrer, followed by a long run at Nickelodeon/Viacom as Director of Content for Nick Online and Editor-in-Chief of ParentsConnect.com. A founding member of the Webby Award-winning GoCityKids, she’s written for Family Fun, Vanity Fair, and New York. Her middle school novel, The Time Boat, is available on Amazon Kindle. Drew keeps the MommyPoppins New York Events calendar spot-on and can be reached at events@mommypoppins.com.
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