After 33 years, a Bainbridge Islander's dream boat sets sail

Just beyond the mouth of Eagle Harbor, Roy Jackson silenced the whining diesel engine onboard his twin-masted wooden schooner. Then, pushed by a timid wind, the Dolores M. Jackson set sail for the first time.

For Roy and wife Dolores – the schooner’s namesake – it was a moment they had been working toward for 33 years.

For three decades, the wooden schooner had been painstakingly handcrafted in the Jacksons’ shop on Crystal Springs Drive. A cast of islanders helped along the way.

After tens of thousands of hours of work, casting off last Friday for the maiden sail was an almost surreal moment.

“It’s emotional,” Dolores Jackson said as a crew of friends prepared to push off the dock in Eagle Harbor. “We’ve poured our heart and soul, and a whole lot more into this.”

Roy Jackson was 43 years old when he paid $1,000 for a set of plans for a 43-foot, double-masted schooner designed by East Coast naval architect Murray Peterson. Jackson had gotten the urge to build his own vessel after helping sail a boat from the Bahamas to Florida.

A job at the advertising firm McCann-Erickson brought the Jacksons to Bainbridge Island in 1974. Two years later, work began on the Dolores M. Jackson – slowly at first. Roy was still commuting to his career job. And as he worked on the Dolores he was training himself in the skills of a shipwright.

Gathering materials took time as well. For three years the Jacksons collected lead weights from local tire shops, which they melted down themselves to form the 10,000-pound ballast for the schooner’s keel.

The work moved incrementally faster as Roy transitioned into retirement, but it wasn’t until June 2007 that Dolores M. Jackson was ready for launch at a yard in Port Townsend. In March 2008, the Jacksons motored the schooner from Bainbridge to Poulsbo, where two Douglas fir masts, each 40-feet long, were lowered into place by a crane. An extension added another 15 feet to the main mast.

The last year was spent installing a traditional sailing rig with the help of friend and former Adventuress captain R. Gordon Sims.

Yacht horns honked as the Dolores M. Jackson, decked out in fluttering pennants, motored away from its private slip in Eagle Harbor for its first sail.

Onboard the Jacksons were joined by daughter Sheryl and a crew of seven friends. Roy had made Sims captain for the first sail, and Sims explained to the crew that there was serious sailing to do that day. On a first sail there are quirks to be worked out of the systems, and it’s not uncommon for a wooden boat to take on water as dry planks high on the hull are submerged.

“Despite the celebratory nature of the trip, it’s also a shakedown,” Sims said.

A light wind was ruffling the water as the Dolores M. Jackson reached the mouth of Eagle Harbor and the crew went to work hauling up four sails – a main, fores’l, stays’l and jib. Roy killed the engine and the boat was quiet, save for the rush of water and shouts from the crew.

Dolores was joined by the Bainbridge-based schooner Shan, and together they sliced across Puget Sound. Near the midway point the crew on the Dolores raised a “fisherman” – a small, triangular tops’l – bringing the sail count to five. The wind had picked up and the Dolores heeled over gracefully, easily keeping pace with the Shan.

Roy was smiling as his schooner scooted toward Magnolia.

“I’ve sailed on sister ships just like this,” Roy said. “But having your own is great.”

On the return trip the two schooners slowed to a crawl as the wind dissipated off Murden Cove. But the breeze rose again as they neared the mouth of Eagle Harbor.

Heeled over on a broad-reach, the Dolores rounded the final set of marker pilings like a barrel racer and stormed on toward the head of the harbor, drawing stares from onlookers aboard a passing ferry.

Five hours after its departure, the Dolores was safely back in its slip.

With a first sail under their belt, the Jacksons are thinking of taking Dolores to Lake Union for the Fourth of July and showing her off at the Port Townsend Wooden Boat Festival later in the summer. With practice, Roy believes he and Dolores will be able to sail the schooner with just one or two extra crew members. Judging by Friday’s sail, they won’t be hard to come by.

There are still a few rigging projects and plenty of cosmetic work left for the Jacksons to complete.

Indeed, work never ends on a wooden boat. But the maiden cruise was the first test for the Dolores M. Jackson, and by all accounts the schooner passed with flying colors.

“It was an A-one sail, I can tell you that,” Roy said. “We didn’t take on any water, she handled properly, nothing broke. It was a very exciting and exhilarating trip.”

Video by Review reporter Sean Roach

View a slideshow of the Dolores M. Jackson's maiden sail below. For even more photos from the cruise and the evolution of the schooner, visit the Jacksons' homepage at A 2007 Review feature on the construction of the Dolores M. Jackson is also available online.

We encourage an open exchange of ideas on this story's topic, but we ask you to follow our guidelines for respecting community standards. Personal attacks, inappropriate language, and off-topic comments may be removed, and comment privileges revoked, per our Terms of Use. Please see our FAQ if you have questions or concerns about using Facebook to comment.
blog comments powered by Disqus

Read the Oct 28
Green Edition

Browse the print edition page by page, including stories and ads.

Browse the archives.

Friends to Follow

View All Updates