The ever-popular autumnal trip around the San Juan Islands delievered in every aspect this year… except maybe the wind.

Throughout each year, anticipation grows, leading to that one-of-a-kind November moment when you cast off the lines and start the motor out to the Round the County start line at 6:30 a.m., joining 878 other sailors across 126 boats for our annual rally around San Juan County. While Round the County is very much a race, it is also a way to enjoy some of the most stunning scenery you can find in yachting. 

For the uninitiated, Round the County is a two-day race that circumnavigates the San Juan Islands starting off of Lydia Shoal, with an invariably festive stopover at Roche Harbor. Hosted by Orcas Island Yacht Club and Friday Harbor Sailing Club, the course alternates directions every year, and this was a counter-clockwise edition.

We were lucky enough to be sailing again on Jonathan and Libby McKee’s custom Bieker 44, Dark Star. Our work was cut out for us as we had a challenging class ranging from TP52s to a J/125; but luckily, we had a crack crew with a plan.

However… to have a plan, you need wind, which we were all short of this weekend!  

Saturday’s motor out to the start line was, dare I say, warm? Almost as warm as our piping-hot burritos, pulled out of the oven on Dark Star (it’s a cruising boat after all). However, once we arrived at the starting area, cruising time was over, and we were faced with the daunting task of picking our way through the sea of boats dotted across Lydia Shoal. 

After a few false starts and general recalls, we had a very average start near the starboard end and soon tacked off to port in search of some more wind and a better lane. We picked up a nice right shift and tacked back towards the Peapods. As we sailed towards Point Lawrence, the wind continued to deteriorate, and the foul tide increased. We managed to poke our way over to the Orcas shore in pursuit of the Riptide 30 Baby Blue, which was zipping along under its sweet Code 55—essentially a flatter, smaller code zero that still sheets to the rail lead. Fortune favored the brave as we tacked around the point, and we managed to find a good lane near shore and stayed out of most of the negative current that slowed up Riptide 41 Blue and TP52 Smoke. 

This began a very tricky phase of the race, as it was difficult to reposition your boat as we all began fetching Clark Island. Sometimes the boats to the east would punch forward in a nice puff; then the wind would fill from the west, and those boats would advance. Eventually, the wind completely shut off near Matia, but not before testing every bow team with a slew of sail changes in very, very little breeze. 

The consolation to this lack of sailable wind was that the weather was absolutely gorgeous. We were all treated to incredible views of Mount Baker and the North Cascades, while some more intrepid drifters were becoming increasingly familiar with the coasts of Matia or Lummi Island as they bobbed several hundred yards from shore. For hours, we had been eying some smoke over to the northeast that appeared to be lying down in an easterly on the shoreline, but that wind never seemed to touch the water and make its way towards us. Eventually, we suddenly saw a kite go up and fill instantly. It was the unmistakable outline of Peter Dennis’s Swan 46 Setri. Soon after, another symmetrical kite went up. This time, it was Rosebud, owned by a collection of top-level 505 sailors—they were making the most of this rather unusual breeze. 

Finally, the wind began to filter down towards the west, and we managed to just get our noses into the breeze and pop our A1 as we sailed toward Patos. Soon, the wind rose above 10 knots, and I meekly suggested, “Peel?” Jonathan enthusiastically agreed, and the bow team plugged in the A2. Up it went and down came the A1. The boat continued to surge forward towards Patos, but we could see that it was getting softer ahead. 

Our fearless navigator, Mike, reminded us that we had to reach the halfway point by the 4:00 p.m. cut-off, which was becoming increasingly questionable. Luckily, we made the cut-off by 3 minutes. Now the wind was truly in, and we set the kite again, bound for Turn Point. After some quick math, we determined we needed a 9.6-knot average to finish by the 6:00 p.m. time limit at Roche Harbor. We pressed on and began to reel in the heroes of the day, who managed to escape with the over 50-footers, Tripp 41 Bandit, modified Melges 30 Maelstrom, and Setri. While there were a few glorious moments when we shaved minutes off our ETA, with the lowest at 17:48, as we neared Turn Point, the math started to turn against us, and we eventually called it quits and motored to Roche where we arrived well after dark. 

As always, the dock tent provided ample entertainment with a harmonica player agreeing to a few encores and hot grills for BBQ’ing.

Sunday brought us more sunshine, a weak northerly drainage breeze, and a difficult starting strategy. Would you take the line bias and start at the starboard end, or would begin to windward and maintain clear air? As it turned out, starting to windward was the smart move with Santa Cruz 70 Westerly and Riptide 35 Ripple getting off to an early lead. However, as time would soon reveal in this game of snakes and ladders, it’s never over until it’s over. 

Spinnakers went up and down, zeroes up and down, and jibs up and down in a sail inventory fashion show—a sign of sail selection indecision from the afterguard on many boats. Then came an incredibly challenging decision: take the long way around and stay in the breeze to the east, or try to minimize distance by sticking towards the shore? In the end, both options worked as long as you committed to one. 

We identified the shortcomings of both options, and at one point, we were nearly the last boat on the water. We regrouped, ate about 5kg of cookies and, by Davidson Rock, had managed to pick our way back to within sight of the leaders. Thus ensued another game of shoots and ladders between the three Bieker siblings (Blue, Riptide 35 MKII Longboard, and Dark Star) and the Santa Cruz 52 Rosebud. 

In the distance, we could see that the line honours leaders were totally parked and realized that finishing would be anything but simple. Blue led the way with their nifty new J0 (a very lightweight, furling jib that goes to the top of the mast, tacks to the end of the bowsprit, but still sheets to the jib track), and we were struggling with just main and jib. However, as the angle opened up, we managed to get the kite on before the boats around us and had a bit of a jump on them. 

We jibed towards Lydia Shoal and had the finish in our sights when yet another wrench was thrown in the works. A total and complete shut down at the finish line. Mist managed to pick their way through the minefield and take a well-deserved line honours victory. Zvi showed some real promise with a top result in Sunday’s race, managing to pip a few of the 52s over the line. We drifted across the finish just behind Blue and Rosebud and began to motor back through the one-hundred boats battling towards the finish line. We saw every stage of chaos on our motor back in—every variation of sail combination, all pointing in the same direction in the range of wind strengths and orientations. It was clear that the finish for the bulk of the fleet was going to be extremely random and chaotic.  

There were lots of great performances throughout the fleet, but the coveted overall prize for 2025 went to Setri. They were followed for the overall podium by Rosebud and Maelstrom. On Dark Star, we took home second in class and fifth overall. 

Each year, Round the County is an excellent reminder that we sail in one of the most diverse sailing venues on the planet. Having now completed my eleventh Round the County, I can’t remember any two races being the same. What I do remember are the many gorgeous sunrises and sunsets we get to experience out on the water in the late fall. Where else on earth do you get nearly 1,000 like-minded people to go out and spend their leisure time messing about on boats in one of the darkest, wettest, and coldest months of the year?

Full Results at roundthecounty.com

Title background photo by Alyosha Strum-Palerm. All photos are by the authors.