Calling all Chicago Mackinac racing Blockheads!
The Chicago Yacht Club Race to Mackinac® is an iconic freshwater offshore race — 289.4 nautical miles up Lake Michigan, starting in Chicago, Illinois and finishing on Mackinac Island, Michigan.
Are you under 25 and sailing the 2025 Mac Race? Simply sign up for the contest below, and you’ll be eligible for the ‘First Blockhead to the Island’ Award. The first one to the island wins! We’ll call the winner up onstage and present you with a plaque during the Sailors’ Celebration and awards on Mackinac Island after the racing. Exact date and time to be confirmed.
This could be you! Last year saw not one, but TWO first Blockheads to the Island, John Sullivan and Charlie Burris! They also broke the race record, finishing in 22 hours, 24 minutes, and 23 seconds onboard Maverick, an Andrews 80.

Have fun, sail safe, and good luck! See you on the Island. ️
Featured image: Barry Butler, Chicago Yacht Club Race to Mackinac presented by Wintrust