The first North Sound race of the year is a predictably great tradition, the good times always surpass questions about the forecast.

Wylie 24, Tanuki, on their way to the overall win. Photo by Julia Soes.

The Orcas Island Yacht Club’s Shaw Island Winter Classic is the first race of the season in the North Sound, and it’s a good reason to get your winter boat projects finished early. This year’s Winter Shaw, as it’s affectionately known, was sailed on Saturday February 10, and although the forecast was not terrific, it wasn’t terrible either. The thing about Winter Shaw is that it’ll always be better sailing weather than you predicted. You may not have high hopes for February racing, but maybe you should.

Winter Shaw begins and ends in Cayou Channel in front of the Orcas Hotel. In fact, the flag on the hotel’s balcony marks the pin end of the start/finish line. From there, it’s a clockwise circumnavigation of Shaw Island, which is just south of Orcas.

For those of us visiting Orcas for the race, there are always good Orcas Island sailors to learn some new tricks from, and even kind souls to take in your derelict crew for a night or two. They may even let you set up camp in the living room and will probably feed you breakfast in the morning—thanks, Ken!

During any Winter Shaw, odds are high that you’ll get parked about three-quarters of the way through. You’ll then make at least one regrettable tack and get passed by someone as you round the far corner of Shaw Island. And chances are, you’ll also make a few good calls and get them back! Wasp Pass is a wily one, and it’s a big part of doing the race.

This year, 14 boats competed in the Winter Shaw ranging from several 22.5-foot J/70s to the gorgeous 49-foot schooner, Sir Isaac. The big tidal exchanges were taking place at night, meaning a mellower day for currents, and a building breeze was predicted over the weekend.

There was a brisk 5-knot breeze for the start, along with a good half-knot current push. It was a pretty clean start for a line that stretches all the way across the channel. The breeze and current were mostly in the middle as we began our trip around the island heading east.

The author and crew aboard Wild Rumpus for Winter Shaw 2024.

Aboard the Santa Cruz 27 Wild Rumpus, we swapped tacks on our way up Cayou Channel (formerly named Harney Channel) in a true upwind easterly. It made sense to take the middle, except when avoiding two ferries that came through passing us and each other while we were going up the channel. Some boats made gains on each of the shores, but mostly it was the Shaw side that paid off.

As we turned the corner to head south through Upright Channel, the wind backed off and we were able to crack off a bit and eventually hoist kites. The game here was to keep the boat moving rather than pointing at the next corner. Sailing hot angles helped, and maybe we were copying the two lead boats that naturally sail those angles. Taking a jibe towards the Shaw Island shore provided some unexpected magic for Rumpus.

Passing the south end of Shaw, the faster boats had an easier time getting away to the next breeze, and there was definitely more money in sailing in breeze than trying to stay on the correct side of a tide line in the San Juan Channel.

Nearing the end of the race, and the foretold location of frequent park-ups, Wasp Pass provided its usual test of wits. It’s fun to catch up to boats who had escaped earlier in the race, but you can’t help knowing that the sailors behind you are thinking the same thing about you. With so many little bays, and the wind changing direction at every turn, you just took your turn moving forward and hoped that the breeze would be kind and let you be the boat with a turn of speed in that decisive final moment.


In the end, Miles Johannessen came out on top with his new super-mod X-Wylie 24 Tanuki. It will be fun to watch this new boat and see how it goes in a real breeze. Finishing first and correcting shortly behind was Nigel Oswald and his all-star crew on the F-25c trimaran, Makika. Aboard Wild Rumpus, we hovered around the J/70s all day, and managed to come in third for the day, just edging out Chris Wolfe on her J/70 Mossy who was the top finishing shorthanded boat.

Dash 34, Pulelehua, navigates Wasp Passage. Photo by Thomas Bridge.

Thank you Orcas Island Yacht Club for another weekend of early season good times!

For the full race results, visit

Title background photo by Julia Soes.