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:

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Contests

OCTOBER 2025 CONTEST

WHAT’S YOUR FAVORITE BOAT MAINTENANCE? This contest is now closed!   The winner has been contacted. Learn more

Contests

AUGUST 2025 CONTEST

Contest closed! Thanks for participating, see you next contest! CAN YOU UNSCRAMBLE THE LETTERS? “lyf FsOt – cAthat

Contests

WIN THE ILYA OPTI & X-BOAT BLOCKHEADS FLAG!

DID YOU SIGN THE BLOCKHEADS FLAG AT THE ILYA DINGHY CHAMPIONSHIPS? Lots of Blockheads asked who gets to

Contests, Regatta

First Blockheads to the Island 2025

In 2025 THREE Blockheads made it to the Island first during the Race to Mackinac. Jack Reiske, Murphy
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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.
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