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Labor Day Weekend in Westchester and the Hudson Valley 2024: Best Things To Do with Kids

Brilliantly colored hot air balloons take flight at the annual Hudson Valley Hot Air Balloon Festival this Labor Day weekend. Photo courtesy of the event
Brilliantly colored hot air balloons take flight at the annual Hudson Valley Hot Air Balloon Festival this Labor Day weekend. Photo courtesy of the event
8/30/24 - By Katherine Dhurandhar

Looking for the best things to do in Westchester and the Hudson Valley this Labor Day weekend? Here are some family-friendly events and activities to add to your list for the holiday weekend.

Fairs and festivals over this holiday weekend include the spectacular Hudson Valley Hot Air Balloon Festival, the Wakanda Celebration 2024, and Twin Star Orchards' Pig Road and apple picking kick off event. Families can also rock out at outdoor concerts like the Swiftie Dance Party at Playland and the West Point Band Labor Day Concert, both followed by stunning fireworks displays.

As the countdown to September begins, check out our end-of-summer bucket list for top things to do before school starts in Westchester and the Hudson Valley.

More Things To Do in Westchester and the Hudson Valley this Week with Kids:

As always, please click through our listings to confirm details—including dates, times, recommended ages, and any last-minute changes—before heading out.

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Things To Do This Weekend in Westchester and the Hudson Valley with Kids

Boscobel Chamber Music Festival

Garrison
Opens Friday, August 30
Boscobel House and Gardens is proud to announce the third annual Boscobel Chamber Music Festival in partnership with the Chamber Music Society of Palm Beach. Over nine days, the festival centers around five public performances featuring some of the most acclaimed chamber musicians in the country, plus wide-ranging educational and community offerings on Boscobel’s historic site. READ MORE

Children's Shakespeare Theatre Presents: Timon of Athens!

Tappan
Opens Friday, August 30
Children’s Shakespeare Theatre brings its modern production of Timon of Athens to three performance venues in Rockland County. Opening night includes picnicking on the grounds of the Manse Barn in Tappan before walking inside to enjoy the show in the air-conditioned luxury of the new Antrim Playhouse. READ MORE

Hudson Valley Hot Air Balloon Festival in Tymore Park

Union Vale
Friday, August 30-Sunday, September 1
Plan your next photo-op as some 75 hot-air balloons paint the sky in a rainbow of colors—or schedule a tethered or full flight of your own. Fireworks, helicopter rides, live music, food trucks, and family activities add to the fun at Tymore Park. READ MORE

WGGCon 2024 at Croton Point Park

Croton on Hudson
Friday, August 30-Monday, September 2
Come play board games in the park, eat barbecue, and engage in general geekery around the clock with the Westchester Gaming Group (WGG) this Labor Day Weekend at the Senasqua Lodge in Croton Point Park. Outdoor movies will be played after dark. READ MORE

Wakanda Celebration 2024 at Traphagen School

Mount Vernon – FREE
Saturday, August 31
Immerse yourself in the rhythms of Africa with live music performances, marvel at the stunning masquerade display, and let your little ones explore the wonders of the children’s village. Children's activities include workshops in African Arts, dancing and drumming, and an introduction to Swahili.  READ MORE

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

New Paltz
Saturday, August 31-Monday, September 2
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

Taylor's Version: A Swiftie Dance Party at Playland Park

Rye
Saturday, August 31
Enjoy a dance party for Swifties featuring the music of Taylor Swift at Playland Park. This special event is part of Playland's Summer Concert Series. Fireworks follow at 9pm. READ MORE

Kids' Sip-and-Paint at Fertile Crescent Cultural Center

New Windsor
Saturday, August 31
Bring the kids for some food, mocktails, and creativity at this back-to-school-themed sip-and-paint event at Fertile Crescent Cultural Center in New Windsor. READ MORE

Labor Day Weekend Pig Roast & Apple Picking at Twin Star Orchards

New Paltz – FREE
Saturday, August 31
Celebrate Labor Day and the start of the orchard's apple season with a pig roast featuring live music and apple picking.  READ MORE

Storytelling with Jonathan Kruk at Harvest Moon Farm & Orchard

North Salem – FREE
Saturday, August 31
Hudson Valley master storyteller Jonathan Kruk entertains and enthralls his audiences with an interactive storytelling show! Kruk is locally renowned for his annual retellings of The Legend of Sleepy Hollow and A Christmas Carol. READ MORE

Bearsville Country Music Festival

Woodstock
Sunday, September 1
Get your boots ready for a toe-tapping good time at the Bearsville Country Music & Dancing Festival! Saddle up for a weekend filled with live performances from top country artists, line dancing lessons, delicious Southern cuisine, a vendor market, and plenty of down-home fun. Free kids' activities include nature trails, painting, pingpong, cornhole, and other games. READ MORE

Hudson River Arts & Crafts Festival at Senasqua Park

Croton on Hudson – FREE
Sunday, September 1
Join your friends on the river this Labor Day weekend at Croton's huge outdoor fall festival. This year, Baked by Susan shares delicious empanadas, sweets, beer, wine, and cider, and there is a booth for kids to make a personalized, sparkly, beaded bracelet. READ MORE

West Point Band Labor Day Concert

West Point – FREE
Sunday, September 1
Celebrate the end of summer with world-class music, historic views, and fireworks at Trophy Point. This annual favorite features performances from the West Point Concert Band, Hellcats, and Benny Havens Band, topped off with a performance of the 1812 Overture with live cannon fire and a magnificent fireworks display.  READ MORE

Nan's Secret Garden Tour at Lasdon Park & Arboretum

Katonah – FREE
Sunday, September 1
Join one of the gardeners on a visit to Nan's Secret Garden at Lasdon Park. Learn about the native plants showcased behind the stone moon gate.  READ MORE

Harvest Festival at Bethel Woods Center for the Arts

Bethel
Sunday, September 1, 2024
Highlighting local farms, artisans, and flavors, this annual farmers market features live music, food trucks, crafts, special offerings, and more. Special attractions for this day include hayrides, a corn maze, henna tattoo artist, pet adoptions, and visitors from Rosehaven Alpacas.  READ MORE

Songs for Labor Day: Workers' Struggles, Organizing, and Unions

Mount Vernon – FREE
Monday, September 2
Celebrate Labor Day by learning about the history of the labor movement and how it has influenced our lives to this day at St. Paul's Church National Historic Site. Enjoy a performance and sing-along of songs made famous by workers, unions, and strikes, with historical commentary by St. Paul’s site manager David Osborn. READ MORE

Pound Ridge Artisan & Vintage Market

Pound Ridge – FREE
Monday, September 2
With more than 70 artisan and vintage vendors, this outdoor craft festival features live music, food trucks, and a family fun area.  READ MORE

Hudson River Valley Ramble: Guided Nature Hike at Westmoreland Sanctuary

Mount Kisco
Monday, September 2
Westmoreland Sanctuary is excited to partner with the Hudson River Valley National Heritage Area to host a guided nature hike as part of the Hudson River Valley Ramble. Weave in and out of fields and forests as you take in the serene beauty of Westmoreland’s educational campus. Learn about nature in the summer, forest and pond ecology, Westchester history, and native plants and animals. READ MORE

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