Here’s an idea. Let’s take everyone’s idea of a normal sailboat race and turn it on its head. First thing we’ll do is have it in the middle of winter. On the coldest day, in fact. Next, let’s get rid of anything hoity-toity-yachty. We’ll invite everyone, from owners of heavy, gaff-rigged non-racing boats to dinghies and board-boats, and no protests are allowed. So, you might see a dainty 20-footer named Underdog nipping at the heels of a 49-foot sled named Sir Isaac whose skipper, winning for the fourth time, quips, “I guess I’m just doomed to win.” Let’s get race committee members acting as judges to position their two rigid inflatables at various marks to watch for spinnaker wraps and other mishaps while commenting, “Ahhhh, carnage, nice.”

Now for the prizes. Instead of a silver winner’s cup, let’s have a genuine wooden peg leg for first place and require the winner to wear it as a handicap in next year’s race. Finally, let’s all have free beer and pizza afterward, at the Northwest Maritime Center. Sound good?

The annual Shipwright’s Regatta on February 25th saw 30 boats tacking and gybing hither and yon, with a few occasionally asking where the course was, or saying things like, “I thought we’d just keep going around until everyone else stopped.” That little gem won the gaff schooner Emerald the Whak-O-Matic Award, for the best use of misspent energy. The five souls who womanned the lovely but low-in-the-water double-ender Havhasten richly deserved the Golden Trident Award for saltiest crew.

One of the more difficult tasks for the race committee was deciding on who should win the Directional Helmet Award, for the boat that missed a mark or otherwise had trouble navigating the course, but Erin came through in fine style. If we had an award for the most starts, she’d get it. Amid some confusion at the line, she started once, decided to re-start, then came back just to make sure, and ended up (we think) racing in a class all her own. Well done, lads. There was much more jollity, but the solo skipper of the almost-submarine Orange Soda summed up the spirit of the regatta when asked, what kind of boat is that? He said “I don’t know!” And promptly won the Wet Ass Award.

As a 20-foot Flicka skipper put it, “It’s the race that most resonates with me.”

This first appeared in the Port Townsend Sailing Association newsletter.


  1. One modification that would be fun — stagger the start based on a rough PHRF rating, so that all boats are predicted to finish at the same time. The now defunct Steed Bonnet Pirate Race in Southport NC used to do this, so the finish was a an extra measure of calamity. Pirate dress was promoted, and water balloons battles were encouraged for any boats within throwing distance, but winter sailing may dictate otherwise.

    • That sounds like a good and proper pirate race, Joey. The staggered start-time, or “pursuit start” was, I think, considered for Shipwright’s, but that requires every boat to have a rating, which is a lot of work for the race committee since most of the boats don’t have them. Anyway, there’s already plenty of mayhem to go around in February. But you’re in luck, the Classic Mariner’s Regatta in June does this, so you’ll have another chance to witness the finish line carnage! Check the website for the Port Townsend Sailing Association for dates and info.

  2. What a fun and hilarious event! I think I would have been right there next to the confused souls and winning an award for “She who does not get it”!

  3. Anyone that ventures out and spends time on the water on a “organized?” winter day deservers an award in IMO.

  4. Being this endeavor is to take place on the first? day of winter, or there about I suggest that a power category should also be allowed but with hp penalties, perhaps 15 minutes/?hp. The mind runs amok. No rudder gets extra points. Those kind of things. The combined age of the crew? Time on the water?

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