The Kickapoo Valley Reserve hosts annual events. Each are fund raisers for education and event programming.

The Kickapoo Reserve Dam Challenge Triathlon challenges participants to compete among the rugged hills of scenic southwestern Wisconsin's rural countryside and the Kickapoo Valley Reserve. Proceeds from this event benefit the Kickapoo Valley Reserve education program. The Dam Challenge Triathlon is a triathlon for 500 folks. Paddle 7 miles, bike 16 miles, and trail run 3 miles.

The Tromp & Chomp offers 8-mile and half-marathon trail run courses, all within the scenic Kickapoo Valley Reserve. Racers will receive a race shirt and a post-race buffet meal of local seasonal foods. Proceeds from this event benefit the Kickapoo Valley Reserve education and events programs.