The Past Winners

Father Benson of Orcas

Father Benson

The Benson Cup

2023 Results (after event)


The Benson Cup, a thrilling sailboat race around Waldron Island, was an adventure filled with cunning tactics and unexpected turns. On October 7, 2023, the wind and currents favored a counter-clockwise route, a decision easily made by captain Jimmy and his crew, Ryan Samantha-Carson aboard the J/70 sailboat, Ad Lib. As they lined up with 14 other boats for the 11:00 AM start, the north-easterly wind shifted to easterly, setting the stage for an exciting race.

As the race progressed, they noticed the Treachery, skippered by Ken Matchley, a top contender for Boat of the Year, taking a bold move by sailing clockwise, opposite to the rest of the fleet. This odd choice raised eyebrows, hinting at a possible strategic play.

Reaching the northeast point of Waldron Island, the wind died down, and the current turned against them, forcing Ad Lib and others to anchor. Two J/70s, Riff and Mossy, eventually broke free, with Ad Lib closely following along the beach to avoid the current. Surprisingly, Treachery was seen moving steadily on the opposite side.

Despite slow progress, Ad Lib managed to navigate around the north side of the island. Approaching Sandy Point, they saw Riff and Mossy pulling ahead towards the west for better current. In Cowlitz Bay, light wind puffs sporadically aided Ad Lib's progress. They saw a consistent line of wind approaching, bringing hope of overtaking the fleet, which seemed to be stalled behind them.

As Ad Lib rounded Pt. Disney, their hearts sank at the sight of Treachery, under full spinnaker in the new breeze, seemingly heading for a close finish. Just then, the new breeze propelled Ad Lib forward at an exhilarating 5 knots. The fleet behind appeared motionless, with several boats even calling to retire due to the lack of wind. Ad Lib, seizing the moment, hoisted their spinnaker and surged towards the finish line.

In an unexpected twist, Treachery suddenly called in to retire, baffling everyone. As Ad Lib crossed the finish line, the realization dawned that they might be the sole finisher. Enjoying their victory beer, the crew remained puzzled until Ken, with a mischievous grin, approached them at the dock. He revealed that Treachery had used a motor to navigate around Waldron, only raising their sails near the end to feign competition. Ad Lib was the only boat to finish in 2023.This devious move explained their sudden retirement and underscored the unpredictable nature of the Benson Cup, making it a race to remember.

Past Results:
2001 2003 2004 2005 2006 2008 2009 2010 2011 2012

2013 2014 2015 2016 2017 2018 2019 2020 2021 2022 2023

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The Benson Cup is a copper tea pot

The party after the 2012 race on the Jones Island dock.