Krazy Downhill Derby | Chestertown, NY | February 21, 2026

Saturday, February 21, 2026
10:00 AM 1:00 PM

Dynamite Hill Recreation Area Dynamite Hill Road Chestertown, NY, 12817 United States (map)

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2026 Krazy Downhill Derby in Chestertown, NY

Chestertown’s annual cardboard sled competition.

Winter in the Adirondacks doesn’t get much more creative—or more fun—than the annual Krazy Downhill Derby, returning to Chestertown on Saturday, February 21, 2026.

Hosted at the Dynamite Hill Recreation Area, this high-energy community event invites families, kids, and local businesses to turn imagination into motion with wildly inventive sleds and a full day of outdoor winter fun.

Part cardboard engineering challenge, part costume parade, and part neighborhood winter carnival, the Krazy Downhill Derby celebrates everything that makes small-town Adirondack winters special.

What makes the Krazy Downhill Derby so fun.

Cardboard sled shaped like a Shark competing in Chestertown's Krazy Downhill Derby. — You never know what’s going to surface at the Krazy Downhill Derby.

The heart of the event lies in the sleds themselves. Participants build gravity-powered creations to compete for prizes in categories such as fastest, most creative, and funniest. Past entries have included a mermaid, a Viking ship, a fire truck, and even a helicopter—setting the bar high for 2026.

Creativity counts just as much as speed, making this a perfect event for families, friend groups, and local businesses looking to showcase their playful side. Spectators line the hill to cheer, laugh, and marvel at the ingenuity on display.

A day of winter festivities

Even if building a sled isn’t on the agenda, the Krazy Downhill Derby offers plenty to enjoy. The event features music, face painting, s’mores, make-your-own sundaes, and other kid-friendly activities that transform Dynamite Hill into a winter celebration hub.

It’s an easygoing, festive atmosphere where neighbors reconnect, visitors feel instantly welcome, and kids burn off energy in the best way possible—outside in the snow.

Event schedule at a glance.

Mermaid sled on Dynamite Hill in Chestertown. — Mermaid sled.

The day follows a simple, family-friendly schedule that keeps things moving while leaving plenty of time to soak in the fun.

10:00 am – Registration opens
11:30 am – Kids’ cardboard sled race
12:00 pm – Krazy Downhill Derby main event begins

Arriving early is a good idea, especially for competitors, as registration and prep happen before the crowds gather.

Rules competitors should know.

Safety and fairness keep the derby fun for everyone. Organizers have a few essential guidelines for participants:

A maximum of four people per sled
Helmets are required for all racers
Sleds must be gravity dependent—no motors allowed
Larger sleds must include steering and brakes
Each sled gets one run per race

These rules help ensure that creativity shines without compromising safety.

Snoopy and donut sleds compete in a downhill derby.

Support Chestertown while you’re here.

Events like the Krazy Downhill Derby play a vital role in sustaining Adirondack communities during the winter months. Visitors are encouraged to make a day of it—grab lunch at a local restaurant, warm up with coffee or cocoa, and browse nearby shops before or after the races.

Supporting local businesses helps keep events like this thriving year after year and strengthens the community spirit that makes Chestertown so special.

Know before you go.

For the most up-to-date details, including weather-related updates, visitors should check the North Warren Chamber of Commerce Facebook page before heading out.

Whether you come to race, cheer, or simply enjoy a winter afternoon filled with laughter and creativity, the Krazy Downhill Derby promises classic Adirondack fun—no lift ticket required.