This weekend, the who’s who of Northwest sailboat racers will converge on Orcas Island for one of the most beloved races of the year, the Round the County regatta.

This year’s race, with 69 boats in six divisions, will feature the largest and fastest fleet in the event’s 22-year history, said race chairman Betsy Wareham.

“We have just about everything,” Wareham said. “We from Santa Cruz 70 to Santa Cruz 27s in size, and ratings from minus 75 to plus 180. This is actually the fastest fleet we’ve ever had.”

As in previous years, the regatta is drawing some of the most familiar names in Northwest racing. Paul LaMarche’s Santa Cruz 70, Neptune’s Car, will be the largest boat in the regatta, which also includes Charles Burnett’s Transpac 52, Braveheart, Carl Buchan’s custom 40, Madrona, Louis Bianco’s Andrews 53, Artemis, and Kevin Welch’s Robert Perry 65, Icon, among others.

The two-day race, which is about 76 miles in total and includes an overnight stop in Roche Harbor, starts on Saturday morning at Lydia Shoal in Rosario Strait, just east of Obstruction Pass. The course goes around Clark, Sucia and Patos islands, then continues down Boundary Pass past the Turn Point Lighthouse on Stuart Island, finishing for the day at Roche Harbor.

On Sunday, the second leg of the course starts in Mosquito Bay, south of Henry Island, and continues south along the shore of San Juan Island, across Salmon Bank and around Lopez, Decatur and Blakely islands to finish at Lydia Shoal.

Taking sailors around San Juan County, the regatta has become a favorite for its breathtaking scenery. But racers also appreciate the course’s variable conditions—the shifting currents and tidal changes, the eddies and winds coming off the various islands.

Sailboats Roxanne and Artemis compete in a previous Round the County race.

To increase the variety, the race course switches direction from year to year. Every other year the boats depart south, heading clockwise around the islands, while on opposite years they depart north, for a counter-clockwise circumnavigation.

“The weather conditions are different every time and the current conditions are different every time,” Wareham said. “That’s all factored in there. It makes it challenging, but also a lot of fun because it’s a great fleet and there’s a lot of competition.”

And the Saturday overnight stop in Roche Harbor provides an opportunity for post-race fun, Wareham said. “It’s 35 miles (each day) and you don’t get beat to pieces. Instead of doing an overnight race in freezing cold weather, you get to stop for the night in Roche Harbor and have another party,” she said.

“There’s a party Friday night, there’s a party Saturday night, there’s a party Sunday night. It’s just a lot of fun.”

Put on by the Orcas Island Yacht Club and the Friday Harbor Sailing School, the regatta was the brainchild of Wareham’s late father, Mike Wareham, and racing buddy Eustace “Sunny” Vynne. As Wareham tells it, the pair thought it would be fun to organize a race around San Juan County. So Wareham, then the fleet captain for the Orcas Island Yacht Club, set about organizing an event.

She chose the Veterans Day weekend, since there weren’t any other races scheduled that weekend. Thirteen boats turned up for the inaugural regatta in 1988 and the event quickly became an annual favorite, continuing on each year since then.

Though the date of the regatta was originally chosen because it didn’t conflict with other events, the timing has been advantageous in another critical way, Wareham said.

“We usually get wind. If you did this same race in the summertime, you would be very unlikely to finish,” she said. “In the summer, we just don’t have the breeze. That’s one reason we hold it when we do.”

Though the second day of last year’s regatta saw little wind, the first day brought 50-knot gusts, causing Buchan’s new boat to lose its mast. Wareham said there have been some spectacular mishaps over the years, but fortunately, no injuries.

“We’ve had some pretty incredible wipeouts, spinnakers torn up and masts come down and things like that,” she said. “But we’ve never had any danger to people or boats, which is a good thing. No one’s ever had to be evacuated off their boat or anything like that.”