Harken Blockheads | Contests

2026 First Blockhead to Mackinac Island

Calling all Chicago Mackinac Youth racers! Are you under 25 and sailing the 2025 Chicago 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

April 2026 Contest

APRIL 2026 CONTEST Show us your #EpicSend moment for a chance to win FREE Harken swag! 👇 How to enter 👇 1. Dig up your best #EpicSend photo. Big breeze, full send, total wipeout—we want it all. 2. Submit your

DECEMBER 2025 CONTEST

December 2025 Contest: Test Your Iceboating Knowledge The deadline to enter is December 25th. You could be the one lucky Blockhead to win some Harken Blockheads gear! Take a stab at our short quiz to be entered. Winners will be

OCTOBER 2025 CONTEST

WHAT’S YOUR FAVORITE BOAT MAINTENANCE? Contest Closed! Make sure you’re a member of Harken Blockheads – it’s the only way to win! Learn more here.

AUGUST 2025 CONTEST

Contest closed! Thanks for participating, see you next contest! CAN YOU UNSCRAMBLE THE LETTERS? "lyf FsOt - cAthat Kcolb" Correct answer: Fly Soft-Attach Block The winner will be randomly drawn from the list of correct answers. Make sure you’re a

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 keep the flag—now’s your chance! Take home the official 2025 ILYA Opti & X-Boat Championships Harken Blockheads Flag. It’s easy—just fill out

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 Roszak, and Torston Thiel were sailing aboard Vogue, a C&C 41 in the cruising division. It was a light upwind race for

Contests, Regatta

The First Blockheads to the Island 2024 are BACK for 2025

2024 First Blockheads to the Island are BACK for 2025 on Andrews 70 “Illuminati" John Sullivan, along with crew member and fellow-Blockhead Charlie Burris, were the First Blockheads to the Island 2024 AND the First to Finish in the Racing

Will You Be the First Blockhead to the Island?

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

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 to the island, they also broke the race record, finishing in 22 hours, 24 minutes, and 23 seconds. John Sullivan and Charlie

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 race — 289.4 nautical miles up Lake Michigan, starting in Chicago, Illinois and finishing on Mackinac Island, Michigan. Are you under 25

First Blockhead to the Island 2023

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?

First Blockhead to the Island

Megan Geith is the ‘First Blockhead To The Island’ in the 2022 Chicago Yacht Club Race to Mackinac®! Megan is 20. She sailed aboard the Beneteau 47.7 'Dakota' from Chicago Yacht Club. They finished in 1 day, 17 hours 34 minutes and

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 up Lake Michigan, starting in Chicago and racing to Mackinac Island, Michigan. Are you under 25 and sailing the 2022 Mac Race?

Introducing…Schmicter!

Until this very moment, the spiky-haired, cool glasses, big attitude Blockheads face man has not had a name. We thought...Darn it, he deserves better! So we asked you! Thanks to all of your wonderful ideas, we found one that fits

BEST BAILER CONTEST

Blockheads love DIY projects. Over the years, we've seen some creative takes on bailers. You know what gets us excited? Not the $20 red bailers you can buy from the store (yawn!), but the duct-taped, painted, stickered-up, and completely customized

Contest: Name The Blockhead!

Here at Harken, we’re facing an ENORMOUS CHALLENGE. The spiky-haired, cool glasses, big attitude Blockheads face man-who-shall-remain-nameless…remains nameless. And darn it, he deserves better! Let’s not overthink this: Within the next two weeks (by Midnight, January 28) we’re slapping a

January Trivia Contest

The deadline to enter was January 28, 2021. One lucky sailor, Eli, was drawn randomly from the list of correct answers and won a Blockheads Dry Bag and Brandana. 👉 Question: In 1983 Australia II ended the New York Yacht

November Trivia Contest

The deadline to enter was November 24, 2020. 👉 Question: Who holds the circumnavigation record for the Vendée Globe? How long did it take this person to complete this legendary, around-the-world, solo, non-stop race? And just for fun, tell us:

Contests, Maintenance & Repair

What’s Your Favorite Boat Maintenance Task?

We were curious...We wanted to know what your absolute favorite boat maintenance task was...so we asked you! You had a lot to say! Here are the results: Looks like Blockheads love splicing! Check out some of the responses on the

August Trivia Contest

The deadline to enter is August 24, 2020. One lucky sailor will be drawn randomly from the list of correct answers to win a Blockheads Dry Bag and Brandana. Must be a Harken Blockheads Member under the age of 25

June Trivia Contest

The deadline to enter is June 25, 2020. One lucky sailor will be drawn randomly from the list of correct answers to win a Blockheads Dry Bag and Brandana. Must be a Harken Blockheads Member under the age of 25

May Trivia Contest

J.J. Smith was drawn randomly from the list of correct answers and won a Blockheads Dry Bag and Brandana. Congratulations, J.J.! 👉 Question: What is the name of this knot? It ties two lines together. Unlike a square knot, this

10 Nuggets of Blockheaded Advice

Since day one, we’ve filled this website with hundreds of tips and videos to help you build your skills. We ran the Think Like A Blockhead Contest to see what kind of advice you would give to other Blockheads. Here's

April Trivia Contest

👉 Question: This month's trivia contest is about team racing. Tell us what a Mark Trap is and why it's used. 👉 Answer: Mark Trap is one of the most common maneuvers in team racing. Use one to allow

February Trivia Contest

The deadline to enter is February 18, 2020. One lucky sailor will be drawn randomly from the list of correct answers for the chance to win a Blockheads Dry Bag and Brandana. Must be a Harken Blockheads Member to win.

The Think Like a Blockhead Contest

WANTED: BLOCKHEADED IDEAS Since day one, we've filled harkenblockheads.com with hundreds of tips and videos to help you build your skills. It's your turn to share. We're in search of the best sailing advice ever. Enter your best tip in

January Trivia Contest

Take a swing at the monthly Harken Blockheads Trivia Contest: 👉 Question: How is it possible for some sailboats to go faster than the wind? 👉 Answer: Sailboats can go faster than the ambient wind because of apparent wind. Once

December Trivia Contest

Take a swing at the monthly Harken Blockheads Trivia Contest. One lucky Harken Blockheads Member will be drawn randomly from the list of correct answers for the chance to win a Blockheads Dry Bag and Brandana. Submit your answer before

November Trivia Contest

Check out last month’s answer to the monthly Harken Blockheads Trivia Contest: 👉 Question: During the Age of Sail, mariners who had survived the treacherous Cape Horn rounding were allowed to wear this piece of jewelry. What could they now

October Trivia Contest

Check out last month’s answer to the monthly Harken Blockheads Trivia Contest: 👉 Question: When was the very first Olympic women’s yachting event, and who won? 👉 Answer: Women’s yachting was first introduced in the 1988 Olympics with a doublehanded

August Trivia Contest

Check out last month's answer and winner to the montly Harken Blockheads Trivia Contest: 👉 August Question: Who is the youngest sailor to sail around the world solo and unassisted? Identify the sailor! 👉 August Answer: Jesse Martin is a

Aiden Martin Is the ‘First Blockhead To The Island’

Aiden Martin Is the ‘First Blockhead To The Island’ in the 2019 Chicago Yacht Club Race to Mackinac More importantly, his team won Section 1. Aiden is 14. He sailed aboard the Nelson Marek 68 Sagamore. They finished in 1

June Trivia Contest

Check out last month's answer and winner: 👉June Question: 2019 marks the 50th running of the famous Transpac Race which starts on July 10th. One of the entries, the iconic black Spencer 63 Ragtime will be making her 17th Transpac

April Trivia Contest

Test your knowledge of all things nautical by taking a swing at the monthly Blockheads trivia question. If your answer is correct, you could be randomly drawn to win a Blockheads Dry Bag and Brandana! Join Harken Blockheads to start

March Trivia Contest

Test your knowledge of all things nautical by taking a swing at the monthly Blockheads trivia question. If your answer is correct, you could be randomly drawn to win a Blockheads Dry Bag and Brandana! Join Harken Blockheads to start

February Trivia Contest

Test your knowledge of all things nautical by taking a swing at the monthly Blockheads trivia question. If your answer is correct, you could be randomly drawn to win a Blockheads Dry Bag and Brandana! Join Harken Blockheads to start

#EpicSend Photo Contest Winners!

Blockheads, we asked to see your epic moments and you did not disappoint! Narrowing so many fun, fast, and all-around awesome photos down to just five winners was not easy. Thank you to everyone for sharing your sailing memories with

Contests, Regatta

Lift Off in Miami

Earlier this month, speed-loving sailors of all varieties descended on Miami, Florida for the most recent edition of the Foiling Week regatta. A coming together of all matters foiling, the event played host to classes like the Moth, UFO, and

Learn How to Fly at Foiling Week / Harken Kidz Trials

>>> ATTENTION: After having received 100+ compelling applications, we have decided to close entries for the Miami iteration of the Foiling Week / Harken Kidz Trials. We have selected the top 8 applications and have since contacted those selected. All

Contests, Regatta

Breeze-On for Blockheads at Charleston Race Week

Sail22 and Harken Blockheads teamed-up again in support of two youth teams competing in the J/70 fleet at Charleston Race Week 2017. Hailing from Annapolis and South Carolina Yacht Clubs, both groups jumped on the opportunity to hone their keelboat

Contests, Regatta

Blockheads Race Bacardi Sailing Week

Blockheads made a splash at Bacardi Miami Sailing Week 2017. Of the thirty six J/70 teams that competed, only eight raced without pro sailors, and only ONE was crewed entirely by youth sailors. Say hello to Team Sail22 / Harken Blockheads!