Calling all Blockheads!

The Chicago Yacht Club Race to Mackinac® is a legendary race — 289.4 nautical miles up Lake Michigan, starting in Chicago and racing to Mackinac Island, Michigan.

Are you under 25 and sailing the 2023 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 on Tuesday, July 26 2 p.m. to 3 p.m. EST.

To be eligible to win, register right here:



March Trivia Contest

The deadline to enter is April 30, 2024. With the correct answer, you could be the one lucky


First Blockhead to the Island

Megan Geith is the ‘First Blockhead To The Island’ in the 2022 Chicago Yacht Club Race to Mackinac®!


Will You Be the First Blockhead to the Island?

Calling all Blockheads! The Chicago Yacht Club Race to Mackinac is a legendary race — 289.4 nautical miles



Until this very moment, the spiky-haired, cool glasses, big attitude Blockheads face man has not had a name.

What exactly is a Blockhead? If you are totally obsessed with how to rig and sail your boat, you might already be one! Join the community of Blockheads to learn more about the sport, engage with others and share sailing experiences. This site serves as the hub for Blockheads globally, where you can discover how to join, media, tips and tricks, contests, and events. This program is all about YOU and we want to hear from everyone! Not seeing something? Your feedback is crucial, feel free to shoot us a comment or message.