“One thing that I love about distance racing is the 10-minute victories,” says Jaime Mack, a few hours into the 2025 Round the County Race.
This annual two-day event organized by the Orcas Island YC and the Friday Harbor Sailing Club circumnavigates the islands comprising Washington State’s San Juan County with a Saturday night stopover in Roche Harbor on San Juan Island. The 65 nautical-mile race regularly attracts triple-digit fleets and unfurls in early November, with even-numbered years rounding clockwise and odd-numbered years taking a counterclockwise course.
The direction matters, of course, because the waters surrounding the San Juans have notoriously strong currents that can leave a fleet parked up or inverted, especially when someone forgets to ply the wind machine with enough Benjamins. Much like the 2025 race.
I consider Mack’s words as we slowly fetch Matia Island, maybe 10 miles into our 34 nautical-mile first leg. While November in the Pacific Northwest is often wet and stormy, and always dark, this particular weekend is a stunner: bluebird skies, sunshine and warm temperatures.
Better still, our skipper Justin Wolfe has assembled a great crew consisting of Ben and Jen Morgan Glass, and Andy and Jaime Mack aboard Ripple (in still water), his Paul Bieker-designed Riptide 35. We’ve never sailed together as a crew, and most of us are new to the boat, but Ripple is well-prepared, and our logistics are carefully sorted.
There are just two hiccups: foul currents and a dearth of breeze.
Still, we’ve had our wins.
Take, for example, the first “chapter” from the starting area at Lydia Shoal, in Rosario Strait, to Point Lawrence, Orcas Island’s northeastern-most point. The smart money, at least temporarily, wagers on the course’s western edge, while we find ourselves milking a thin kelp- and rock-dodging breeze that carries us east, then north.
Flash forward two hours, and we’re slatting in lumpy waves next to other boats that started with us, temporarily looked smarter, only to be (closely) examining our sheer line or transom at this next restart.
I savor this 10-minute victory, as the rest of the day looks challenging.
The Round the County Race has a long history of temperamental winds, so the Sailing Instructions require boats to record their times at the legs’ halfway points, perchance it becomes impossible to finish the complete legs by the 1800 cutoff.
Such is our fate aboard Ripple, as it becomes clear by 1430 that our objective is evolving from finishing the leg to fetching the halfway mark by its 1600 deadline.
Still, math is math, and the VHF calls start at around 1530. We aren’t happy to announce our own retirement 10 minutes later, but the last 2 miles will be someone else’s 10-minute victory.
We tuck Ripple into its berth three hours later, and the reason for the race’s strong local following refocuses: Sailors, bundled in winter jackets, mingle on the docks with libations and victuals. There are a few groans about the day’s breeze, of course, but most scuttlebutt that I overhear involves sunshine and warm temperatures. This is my fifth time doing this race, and every year is different, from torrential rains to big breeze to frigid temperatures, but the race is (usually) good sailing, has a laid-back vibe, and the chance to hang with friends in Roche Harbor are—for me—its gravity.
We nail our boat-end start the following morning, and we assume a windward lane as we reach toward San Juan Island’s Hanbury Point. Our A1.5 spinnaker is pulling, and after yesterday, 7 knots of Speed Over Ground feels big.
We shift gears several times between the J1.5 and the A1.5 and commit to an offshore lane that gives us fine views of San Juan Island’s western shoreline. Jibing Ripple’s kite is easy in the 10 to 15 knot breeze, and the boat’s water-ballast system, combined with our active crew ballasting, keeps us rumbling.
Mount Baker’s glaciated summit appears as we reach San Juan Island’s southern flanks, and, eventually, the leg’s halfway point. But as we pass Colville Island, in the Strait of Juan de Fuca, the missing Benjamins again become problematic.
We push up Rosario Strait, bucking a 2-knot current and hanging onto increasingly fickle fingers of wind with Ripple’s A1.5.
Mack’s words about 10-minute victories play out again as our section of the fleet negotiates Bird Rocks. We opt for a westerly routing, but for a pregnant hour, the smart move looks to have been the easterly line. Jen Morgan Glass, our tactician, and Wolfe work some magic, linking scuffed-up stretches of brine amongst swaths of greasy-looking saline, while the rest of us keep the sails—and mood—trimmed.
It works, sort of.
Our position, which had been looking bearish, transitions into another 10-minute win, before the bottom falls out. Flow detaches from our foils, and nothing budges our SOG above zeros. Painful.
Mountaineers say the final 5 feet are the crux of any climb, and this truism resonates as we stare at the finishing line for what feels like hours. We’re talking frisbee range, but bow stems are all that matter.
And we’re not alone: the nearby fleet compresses, all of us parked, as we rifle through headsails and kites. All options hang limply as the sun slouches west.
We drift toward the finish line in a tight scrum-cum-rulebook-knowledge-melee. We finally catch the RC’s finishing whistle and clear out, making room for others who are still fighting for their final five feet.
The day’s bonnet blue sky fades to black as stars and a waning gibbous moon punctuate our delivery back to the Orcas Island YC. I burrow into my down jacket and consider how celebrating 10-minute victories helps to justify hours of hard work while also distributing the day’s dividends more widely across the fleet than mere award-ceremony hardware.
Granted, it would be nice to use some of these dividends to bribe next year’s wind machine, but it wouldn’t be a full value Round the County Race without restarts, challenging currents, kelp, and the tapping of local knowledge.
But hey, at least it didn’t rain.
