Challenge Cup is the creation of Boogie Wainui. It was named this simply because it was a challenge to the merchants. As a clerk at Young Brothers at Kahului Harbor, he worked with all the trucking companies on Maui. He did not create this race as a fundraiser but to help the merchants with their business and as a family community event. The Challenge Cup also helped the club recruit.

The structure of the event was straight forward. Ask what personnel each company had available to paddle. There were also personal challenges within the race, as trucking companies wanted to challenge a particular company. Prizes for best crew uniforms, best cheering and best tent set-up were also given.

In the early days, prizes included cases of soda, broken canoe paddles turned into trophies and recycled trophies. Expenses were kept to a bare minimum.

We run 1/8-mile sprints with multiple heats. Divisions usually include Novice, Open, and Keiki. NKE provides steersman if needed and practice can be arranged if wanted.