Greg Gilbert’s 1926 Lake Union Dreamboat, Winifred. Photos by Greg Gilbert

For almost 30 years, Greg Gilbert dreamed of reclaiming victory at the Victoria Classic Boat Festival.

In 1983, Gilbert won the festival’s coveted best of show award for his 1930 36-foot Blanchard powerboat, Mer-Na. After selling the boat in 1987 and buying his 1926 Lake Union Wooden Dreamboat, Winifred, in 2000, Gilbert set his sights on a second win.

“It’s been my dream to come back to the show with another boat and win again,” he said.

Gilbert moved aboard Winifred and worked endlessly on his floating baby, becoming known among his dockmates at Seattle’s Stimson Marina as “the midnight varnisher.”

He started entering Winifred annually in the Victoria festival, winning awards for best tender and best liveaboard boat in 2008 and 2010, respectively.

But the top prize eluded him. He was often competing with boat owners with resources to hire teams of artisans to maintain their vessels, a luxury that Gilbert, a staff photographer at the Seattle Times, does not have.

“There were some years that was kind of anxious and hoping maybe it was my year, but it didn’t happen,” he said.

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Watch the audio slide show about Greg Gilbert and Winifred below:

Gilbert ramped up his efforts this year, repainting Winifred‘s hull, painting the foredeck and revarnishing her exterior. A couple of days before leaving for the Victoria festival, held over the Labor Day weekend, Gilbert was still revarnishing after dark with floodlights on the railing of the boat, which he keeps in a covered slip.

His faithful dedication was finally rewarded — Winifred won the award for Best Overall Powerboat at this year’s festival.

Gilbert was hopeful for a win this year before learning that Olympus, a stunning, immaculately maintained 97-foot 1929 fantail yacht and a perennial festival winner, was competing in Victoria again after a multiyear break.

Gilbert’s hopes were dampened. But he had a new arrow in his quiver, a 1923 Johnson Waterbug brass and bronze outboard engine he bought on eBay. The two-horsepower engine had been restored and polished to a mirror-like shine.

Winifred’s tender, Fred.

When Gilbert took the engine out and put it on Winifred‘s tender, people began coming over and asking about it. More judges than usual toured Winifred, Gilbert said, asking if he was attending the awards ceremony.

“I’ve never had so many judges on the boat, and they were all so complimentary,” he said. “One said, ‘When you come on the boat, it’s like turning back the clock.’”

Hearing his name announced at the awards ceremony on the last day of the festival, Gilbert was ecstatic.

“This is a big thrill for me,” Gilbert said. “I was honored.”

About Deborah Bach

Deborah Bach is the editor and co-founder of Three Sheets Northwest. She is an avid sailor and longtime professional journalist. You can find Deborah aboard her Passport 40, Meridian, with her husband Marty and their cat Lily.

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