Throughout her career, Bellingham resident Deb Dempsey has been no stranger to danger, nor challenging the status quo. Dempsey, now 75, was the first female Columbia River Bar pilot, making her a trailblazer in an industry mostly made up of men.
The Columbia River Bar, or entrance to the Columbia River near Astoria, Oregon, is one of the most dangerous stretches of water in the world, with an amalgamation of high-speed winds, rushing tidal currents and shifting sand bars culminating in dangerously high seas. Expert pilots such as Dempsey climb aboard large ships and guide each crew through the bar with exacting preparation for the challenging conditions.
Dempsey trained for several months in December 1994 before receiving her license, as the organization requires the highest licensing standards of any pilotage in the U.S. to ensure safety of crews and cargo.
Not only was Dempsey the first woman to graduate from a maritime or service academy in the country, but she was also deck student valedictorian of an 88-member, all-male class at Maine Maritime Academy. Dempsey excelled in courses from celestial navigation to seamanship, along with a balancing act of three work-study jobs.
She had to face blatant disrespect, she recalled.
“You get spat on, you get a rock thrown through your window,” Dempsey said. “Not all of them were like that, but because I put blinders on, I found what I wanted to do.”
While diversity in the maritime industry has grown over the last several decades, the pilot organization has yet to hire another woman. It’s a highly selective field, with fewer than 1,300 ship pilots working throughout the country.
Co-founder of Community Boating Center
Outside of her 22-year piloting career, she co-founded the Community Boating Center near the Bellingham Ferry Terminal in 2007, now volunteering about eight hours a week and acting as treasurer for the center’s board of directors.
Dempsey can’t help but notice how much the center’s programming has grown from its start, as she squints to watch a group of children in sailing camp. A line of kids wearing life vests glide through the water, one by one, forming a circle around the buoys they’re instructed to follow.
Since the CBC’s inception, Dempsey noted the overwhelming growth of community interest, a result of the boating center’s commitment to inclusivity within outdoor recreation.
Over the years, the center has partnered with community organizations such as the Max Higbee Center, which provides recreation programs for youth and adults with developmental disabilities, the AIROW Project, that also provides recreation opportunities for those with disabilities, and Shifting Gears, that seeks to empower women through outdoor recreation.
In April, the boating center unveiled the completion of its highly anticipated Wheelhouse Building Project, marking a major milestone in improving accessibility in recreational boating.
Dempsey explained that once the small watercraft dock receiving permits through the Port of Bellingham is finished, they will secure adaptive equipment for individuals with disabilities.
“Sharing the story, filling a need, putting passion into action,” as Dempsey puts it, referring to the overarching mission of access for all on the water.
The mission on a smaller scale? “Seeing the smiles on participants’ faces from age 5 to 85!” she added.
It’s not uncommon to run into Dempsey on one of the docks, or on the water, calling out words of encouragement to other sailors.
The boating center’s executive director Bryan Rust worked with Dempsey to bring in accessible boating equipment.
“Deb and I are kind of two peas in a pod, so it was a pretty fast friendship,” Rust said of their first encounter in 2020. “I think we just align on sharing values via our time spent on the water and what that’s meant to us.”
Rust admires the various characteristics of the former mariner, fascinated by how Dempsey’s current job differs from her past as a pilot.
“She’s such a straight breed of character,” he said. “She perceives things that most people, I don’t think, see pretty quickly.”
Her former career plays a major role in how Dempsey approaches her work at the boating center. She recognizes the importance of being successful on the water, wherever you may be.
Love for the water at early age
Dempsey was born in 1949 in Essex, Connecticut, a town at the mouth of the Connecticut River and known for its strong network of boating and sailing communities.
At age 3, her parents and their friends opened the Pettipaug Junior Sailing Academy. She said she was surrounded by their teaching and love for the water from an early age.
One of Dempsey’s fondest memories is constructing a 13-foot Blue Jay — a small sailing dinghy — with her family in their home garage.
At age 12, Dempsey entered competitive races that yacht clubs throughout New England hosted each week.
“Learning to be successful on a small boat really helps being successful on a big boat,” she said. “You just have that innate sense of what’s going on.”
As a teenager, she attended the Williams School, a private school in New London, Connecticut, and continued to race for the same yacht clubs. Then, she traveled four hours north to study chemistry and math at the University of Vermont.
After graduating from UVM, Dempsey delivered yachts for three years before she started at Maine Maritime Academy in 1974, a suggestion from her father’s friend.
“He said to my dad, ‘Why doesn’t Debbie go up there and learn what she really wants to?’” she said.
At the academy, Dempsey was required to take three years of Coast Guard classes and six months of sea time as a cadet on Maine Maritime Academy’s training ship, and with a commercial company. All this was compressed into just two and a half years.
Shortly after graduation, Dempsey joined the International Organization of Master Mates and Pilots, up until 1994, when she received a call on April Fool’s Day from Captain Paul Jackson, former president of the Columbia River Bar Pilots.
But he wasn’t joking when he asked her to consider becoming a Columbia River bar pilot.
“When I first went there, we were working 22 days on, 22 days off … so you really get beat up in the wintertime by the weather,” Dempsey said.
In 2012, Dempsey was reminded of what made her job so harrowing. During a transfer, in which a pilot moves between the pilot boat and a vessel via a rope ladder, Dempsey became sandwiched between the two boats, dangling above the water. Her colleagues brought her back onto the deck, thanks to their significant training for situations such as this.
Piloting the path for other women
Another woman to break into the industry, Sandy Bendixen, is one of Dempsey’s mentees and has served as a Puget Sound Pilot since 2018.
As Washington’s first female pilot, Bendixen guides large cargo and cruise ships in and out of Puget Sound, drawing from her knowledge of waterways, docks and hazards that may impact a vessel’s safe passage.
A fellow Maine Maritime graduate, Bendixen “always knew” she wanted to work as a pilot. After Bendixen’s freshman year in Maine, the president of the academy mentioned Dempsey.
Her career piqued Bendixen’s interest, and that summer he suggested meeting Dempsey in person and grabbing coffee.
Dempsey responded with, “Absolutely not,” taking Bendixen by surprise. But Dempsey followed with, “You can come down to Astoria instead and work with me for two weeks.”
Looking back, Bendixen said she cherishes Dempsey’s teachings about confidence. As Bendixen transitioned from a ship captain to a pilot, she sent constant updates to Dempsey.
“There’s a fine line between confidence and overconfidence, and you just have to do your job well,” Bendixen said.
By her retirement in 2016, Dempsey had guided thousands of ships across the Columbia River Bar.
Now, with almost two decades of experience under her belt at the Community Boating Center, Dempsey said she is elated to pass down her leadership role in the future to “very competent staff and board members” who will outlive her.
