Chestertown’s Krazy Downhill Derby 2025

Wild and wacky winter fun on Dynamite Hill.

Chestertown’s annual downhill derby is always entertaining.

Don’t miss Chestertown’s annual Krazy Downhill Derby at the Dynamite Hill Recreation Area.

Watch as community members of all ages vie for prizes for the fastest, most creative, and funniest sleds. In the past, there has been a mermaid, a Viking ship, a firetruck, a helicopter, and other unique sleds. Use your imagination and start creating.

It’s more than just a cardboard sled race. The Krazy Downhill Derby also includes music, face painting, s'mores, make-your-own sundaes, and other fun activities.

If you plan to compete, a few particulars to note:

Get creative with your Krazy Downhill Derby entry.

• Four people per sled (max)

• All racers must wear helmets and sleds must be gravity dependent

• No motorized vehicles and big sleds must have steering with brakes

• Big sleds also have a maximum capacity of four people

• Sleds can only go down once in both races

• Registration starts at 10 am

• Kids’ cardboard sled race begins at 11:30 am

• Krazy sled racing begins at 12 pm

Come and watch the Krazyness even if you're not competing - it's tons of cool outdoor winter fun!

For current information, visit the North Warren Chamber of Commerce website.

Lil’ ADKers get in on the Krazy Downhill Derby Action in Chestertown. Photo credit: Brandon J. Himoff.

Places to eat, shop, stay and things to do near Chestertown.

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Listen to our episode featuring Gore Mountain. Hear about what’s new at Gore, it’s history as one of America’s oldest ski resorts, and future enhancements.

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Navigate to Dynamite Hill in Chestertown.