While looking for a summer job during high school, Emily deBettencourt found her way to the Oak Bluffs harbor. She wasn’t water savvy and at the time knew practically nothing about boats. But with friends already working at the marina, she thought the mooring attendant gig could be a great way to spend the summer.

Then she got hooked.

Nearly 10 years later, Ms. deBettencourt can still be found working around the Oak Bluffs harbor, but now with a wealth of experience and a new title: harbor master.

Emily deBettencourt, assistant harbor master Maeve Rice and office manager Jennifer Goeckel take a spin in the harbor master's boat.

Jeanna Shepard

Emily deBettencourt, assistant harbor master Maeve Rice and office manager Jennifer Goeckel take a spin in the harbor master's boat.

Jeanna Shepard

For years, Ms. deBettencourt served as assistant harbor master to longtime harbor master Todd Alexander until his retirement in spring 2021. She officially stepped into the lead role earlier this year.

“Todd was here for almost 30 years. He’s an enyclopedia of the Oak Bluffs harbor, Oak Bluffs in general, boating . . . pretty much everything,” she said. “Right now, I feel like I learn something new every day. I hope that I’ll know it all one day.”

But Ms. deBettencourt isn’t captaining the harbor all on her own. She recently appointed Maeve Rice as assistant harbor master, and the two are working hard to get the marina ready for the summer.

Ms. Rice grew up sailing around the Island and is no novice on the water. Between busy seasons at Offshore Ale Company, where she bartended for the past five years, she embarked on various sailing expeditions, traveling most recently on a catamaran to the U.S. Virgin Islands.

She said she feels most at home working on the water.

“[I am] exactly where I want to be now,” Ms. Rice said. “It’s been like a family ever since I’ve been here, even though I’m the new person.”

Ms. deBettencourt hopes the entire harbor staff feels the same way. She doesn’t take the “master” in her name too seriously, and wants harbor management to be a team-driven operation. In the office, she sits beside Jennifer Goeckel, who has been managing the office since her early days as a mooring attendant. She described Ms. Goeckel as the “brains of the harbor.”

Ms. Goeckel said that since Ms. deBettencourt’s promotion, she has had the opportunity to get more involved with the workings of the harbor. As a lifelong sailor, she enjoys opportunities to step out of the office and spend time on the docks.

“[Todd] just knew so much, and now everybody’s learning and working together,” she said.

Harbor management is a field historically dominated by men, and Ms. deBettencourt is currently the Island’s only woman harbor master.

Jeanna Shepard

Harbor management is a field historically dominated by men, and Ms. deBettencourt is currently the Island’s only woman harbor master.

Jeanna Shepard

Harbor management is a field historically dominated by men, and Ms. deBettencourt is currently the Island’s only woman harbor master. Ms. deBettencourt said that she still has to prove her place on the water.

“I feel like people can easily pick up on confidence or lack of confidence,” she said. “When I was younger, people would be like, ‘Do you have any guys in the office to help me with this?’ That happens all the time — ‘We need a guy.’ One time, someone was asking for that and we sent out our smallest little kid, Charlie.”

Thankfully, she added, most Islanders and other harbor masters have shown her and her team lots of support.

“We were walking down the harbor and it was a nice day with people out for the beginning of the season, and everyone was just congratulating her,” said Ms. Rice.