Surfski! Downwind! 110% Paddling with Oscar Chalupsky

Googling "downwind paddling" gives limited results. In my searches, I found myself reading the same few articles over and over, trying to grasp what I had tasted in Guadeloupe, where the tradewinds that delivered Columbus to the Caribbean still blow. One article I reread was a post on the TC Surfski website. Since I had never surfski'd I reread the post with interest but kept sweeping the internet looking for more opportunities for outrigger downwind. TC Surfski, however, kept popping up. I ended up on an email list, and I discovered in my inbox one day an invite to downwind surfski immersion with TC. I ignored it. Then, after some time, I saw it again and actually read it: beginners welcome.

I signed up.

I bought my ticket to an area of Michigan I had never heard of, via the curiously named Cherry Capital Airport, and prepared for another fool's adventure, this time into a paddling realm I knew only two things about: surfskis go faster than outriggers (less drag) and paddlers fall off of them all the time. I jokingly referred to the upcoming immersion as my "submersion."

Now, what occasionally gets washed. The shirt or the paddler?

Now, what occasionally gets washed. The shirt or the paddler?

I started paying more attention to this chap named Oscar Chalupsky, who was to be our main instructor. I was fascinated by his Youtube videos, though I couldn't really grasp what he was seeing in the waves in front of him, no more than I had vaguely grasped what was happening with the waves in the Caribbean Ocean in January. I had scoured for online resources and possibly books about waves and finally settled on WAVES by Frederic Raichlen. Raichlen swears he won't bury the reader in math in the terse intro then promptly buries the reader in formulas. I wasn't about to turn a page without understanding a single formula, so I very slowly started making my way through the book, starting here:


L (length)L=P(SQ)* 1.56mLength

P (period)L=P(SQ)* 5.12fLength

After a few months I was still poking my way through the math and learning a lot, but I wasn't paddling. I figured if I could ask Oscar what he was looking at when choosing his runs, if I could learn one thing about what he was seeing, what he understood, the surfski immersion would be worth it. I packed my book on WAVES and my neoprene but not my GoPro camera. Who in the world would want to watch footage of my rolling face-first into Lake Michigan over and over again?


Oscar taught me a little something when I showed him this book. Trick question: How many waves do you see on the cover?

Lucky me learning side saddle stability and bracing in the 2ski with Oscar.

Lucky me learning side saddle stability and bracing in the 2ski with Oscar.

As a total beginner the one thing I couldn't take with me was a surfski. Oscar easily remembered my name and playfully growled at me I was to paddle with him in a double to start. One rarely has the opportunity in life to learn from a master, especially from the very beginning. I was very fortunate to have excellent surfski paddling instilled in me from minute one. In the hours that followed, Oscar dutifully deconstructed paddling and provided insight into downwind I will certainly never forget. Thanks to Oscar, I never rolled off the surfski, I got a cool shirt with awesome fine print in keeping with Oscar's sense of humor, and I know something about waves that changed my life. Thanks to local Andrew Amato for capturing this awesome drone video. Stay tuned this summer. I will be deconstructing outrigger paddling Oscar style and fine-tuning the fundamentals.

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