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Labor Day Weekend in Westchester and the Hudson Valley: 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
8/30/23 - By Katherine Dhurandhar

Looking for the best things to do in Westchester and the Hudson Valley on 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 and Wakanda 2023, a celebration of African culture and fashion. Families can also rock out at the Bearsville Jazz and Arts Festival or celebrate the start of the apple-picking season in the Hudson Valley at Twin Star Orchards' Pig Roast and Apple Picking Celebration.

As the countdown to September begins, be sure to 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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The Bearsville Jazz and Arts Fest brings live music, unique artwork, and plenty of family fun to Woodstock on Sunday. Photo courtesy of the event
The Bearsville Jazz and Arts Fest brings live music, unique artwork, and plenty of family fun to Woodstock on Sunday. Photo courtesy of the event

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

Hudson Valley Hot Air Balloon Festival

Union Vale
Friday, September 1-Sunday, September 3
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. READ MORE

Boscobel Chamber Music Festival

Garrison
Opens Friday, September 1
Boscobel House and Gardens is launching the first Boscobel Chamber Music Festival in partnership with the Chamber Music Society of Palm Beach. The event is led by artistic director Arnaud Sussmann. The festival kicks off with the Emerson String Quartet with the first performance of their farewell tour. READ MORE

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

New Paltz
Saturday, September 2-Monday, September 4
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

Wakanda 2023

Mount Vernon–FREE
Saturday, September 2
Celebrate the heritage of Africa with an all-day festival featuring a fashion show, shopping, food, and live performances that include African dancing and drumming. Kids can also enjoy storytelling, crafts, and Black Panther character appearances. READ MORE

Late Summer Habitat Walk

Rye–FREE
Saturday, September 3
Join a park naturalist for a guided walk around Marshlands Conservancy and see what's happening in late summer in the park. Marshlands' 147-acre wildlife sanctuary is composed of diverse habitats, including forests, meadows, salt marshes, and one-half mile of shoreline along the Long Island Sound. READ MORE

Community Day 5K and Family Fun Run

Cold Spring
Saturday, September 2
The Village of Cold Spring Community Day includes music, food, face painting, balloons, games, circus fun, and more! The event is kicked off by a 5K and Fun Run, a charity fundraiser. READ MORE

The Hudson River Music & Comedy Fest

Peekskill–FREE
Sunday, September 3
What better way to cap off the summer of ’23 than with a free concert on the banks of the Hudson? Celebrate Labor Day with an amazing line-up of comedy and music.   READ MORE

Labor Day Weekend Pig Roast & Apple Picking

New Paltz–FREE
Sunday, September 3
Celebrate Labor Day and the start of the orchard's apple season with a pig roast featuring live music and apple picking.  READ MORE

Bearsville Jazz & Arts Festival

Woodstock
Sunday, September 3
Celebrate Labor Day Weekend with world-class jazz plus painting demonstrations by the Woodstock School of Art. The park features a "gallery in the woods" plus a hand-built house using recycled materials, open for children of all ages to bring to life with paint and other crafting materials (all supplied). READ MORE

Town of Southeast Fireworks Extravaganza

Brewster–FREE
Sunday, September 3
Enjoy an evening of fireworks with a DJ providing live entertainment in the parking lot in front of DeCicco’s.  READ MORE

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

Mt Vernon–FREE
Monday, September 4
Celebrate Labor Day by learning about the history of the labor movement and how it has influenced our lives to this day. Musoc historian Robert Cohen sings and interprets songs of the labor movement.  READ MORE

Labor Day Race/Walk & Kids Fun Run

Warwick
Monday, September 4
Presented by the Warwick Lions Club, this race includes a five-miler, a 5K, and a children's fun run (100, 200, or 300 yards), as well as a DJ, prizes, and refreshments. This year marks the 32nd annual event. READ MORE

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