The 2025 edition of the Shaw Island Winter Classic was on par with the prior runnings in almost every way, other than maybe the most important one, the direction.

During the Summer Shaw, you get to choose your rounding direction and you get the joy and pain of guessing whether you went the right way, but at the Winter Shaw the race committee decides for you.  

In June, when you sail the Round Orcas Race, the direction is decided by democratic vote of the racers. But the Winter Shaw is not your choice and has been clockwise for at least 20 years, right up until this year. To be accurate, right until the evening before the race. It’s true that we had a very frigid week before the event, and it’s true that the wind forecast was light and the possibility of current was significant, but we all found out that it was possible to go the other way in the winter.

Speaking of frigid, all the schools in the North Sound spent the week with late starts and snow days, and the forecast for race day was far from balmy. One of my trusty race crew suggested doing the race in survival suits. I replied that I was planning on wearing my sub-zero down jacket and that I would have my Mr. Buddy Heater with three cans of propane for the adventure. She may have replied that sub-zero down and survival suits are pretty much the same, but I humbly beg to differ. 

And speaking of crew, in addition to my friend Mark Harang and my son Dylan (who often sail Wild Rumpus with me), I was also joined by the crew I’ll be sailing with for the upcoming WA360 Race on Team Salish Seasters. It’ll be a challenge that’s not in my racing wheelhouse, but it will also be a great adventure! We have big plans for getting our biking legs in shape and testing the waters of the South Sound, but our first test was a February sail through the islands.

On race day morning, I fired up coffee and three thermoses, and loaded up the car to find out that it was at least 10 degrees warmer than predicted. Things were already better than expected. After eventually getting the outboard to start on a cold morning, we motored to the Orcas Island ferry landing. The sun was shining, the breeze was light but not nothing, and the current was not enough to visually notice from the dock. 

The starting line is the entire stretch of Cayou Channel (formerly Harney Channel) which can be a bit hard to judge, and this time from the opposite direction. As happens, we thought we were dangerously close to the line, and some boats were well ahead of us, and the race committee from the peanut gallery on the Orcas Island shoreline called out on the radio “ALL WELL CLEAR” at the start. Well, ok then! Off we went.  

Fairly soon we went to kites, and it was light but some puffs rolled through and made a few moments exciting. Most of the lead boats had asymmetrical spinnakers that were barely brushing the water in front of them, meaning they occasionally had surprising moments of land and rocks and other boats in their immediate future. On my Santa Cruz 27 Wild Rumpus, we caught some great surprised expressions right behind some big kites, particularly a smiling face of Chris Wolfe on Ripple just off our transom and Bob Brunius calling out, “Don’t hit Steph!” from behind the kite of the J/70 A-ha! With no faces to be seen!  

For the most part, we made it through Wasp Pass unscathed, and there weren’t a lot of passing lanes in San Juan Channel. Getting too close to Shaw Island proved to be slow, and we weren’t sure if we were going to finish at the short course off Flat Point on Lopez Island. Again, the short and full course finishes were the width of the respective channels.  It made a difference if you were planning to finish there, or if you were going to connect the dots to round the last corner to the finish. As it turned out, we did the whole course. And we even did it in a reasonable time, with the sun shining. 

Sure, it snowed on us shortly after the start, but mostly it was just a beautiful day on the water with a delicious awards dinner at the Orcas Hotel and a fun slumber party on the island afterward. Maybe the frigid weather scared away some boats this year, but if there’s a lesson to be learned—the weekend was far better than the forecasters predicted and things are almost always better than your worst fears. You just had to get out there and give it a go. 

This year the podium places went to our Wild Rumpus crew; Justin and Christina Wolfe sailing doublehanded on their new whip, the Riptide 35 Ripple; and Rhys Balmer also sailing shorthanded with his Soverel 33 Elsewhere.

Results can be found at oiyc.org.