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

RECOMMENDED

Contests

The First Blockheads to the Island – New Race Record!

The 2024 Chicago-Mackinac was one for the record books. Not only were there TWO Blockheads who were first

Contests

First Blockhead to the Island 2024 – Could It Be You?

Calling all Chicago Mackinac racing Blockheads! The Chicago Yacht Club Race to Mackinac® is an iconic freshwater offshore

Contests

March Trivia Contest

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

Contests

First Blockhead to the Island 2023

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


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.