BOOTHBAY HARBOR, Maine — Decades-old technology will pit itself against technology as old as mankind itself in a race next Monday, and the outcome likely will depend on which way the wind blows.

At 7 a.m. Monday, the schooner Timberwind will set sail from Rockport, while Aquilino Alamo, a Boothbay Harbor-based physician, laces up his running shoes for the 42-mile run to Boothbay Harbor. Though winning isn’t his primary goal, Alamo said he’s hoping for wind in the face of the schooner to slow it down.

“Fortunately or unfortunately for me, I’m the only crazy runner they know in town,” said Alamo. “As long as they’re not pressed for time, I will run the whole course.”

On the sea side will be Joe and Bob Tassi on the 98-foot schooner Timberwinds, which from 1931 to 1969 served as the pilot ship in Portland Harbor, meaning it met incoming ships so local captains could navigate them into port.

“The Alamo family could end up beating the pants off us if the wind and tide don’t work with us,” said Joe Tassi. “If the wind is at our nose all day, it could really foil our efforts.”

While the crew of the Timberwinds enjoys homemade corn chowder cooked traditionally on the Timberwinds’ woodstove, Alamo will depend on fluids and food provided along the run by his family.

The event is designed to kick off the 50th annual Windjammer Days Festival in Boothbay Harbor, which runs June 24-27. Alamo, an internal medicine doctor who works for Lincoln County Healthcare, said he took on the challenge so he can follow the same advice he gives his patients on a nearly daily basis: exercise.

“Hopefully I can promote an active lifestyle,” said Alamo, who prior to 2002 worked in the Machias area for four years. “If I can inspire one person or one family to do that, it’s well worth the effort.”

Alamo is no stranger to running long distances. He has competed in a dozen marathons and several triathlons, including some of each already this year. He has a long-term goal of running a marathon in each of the 50 states by the time he’s 50 — but at age 45, he said he might be a few years late in reaching that goal.

“I’m not a very fast runner,” he said. “I’ve run a dozen marathons but I don’t win them. For me, it’s not how fast you are, it’s how good you look when you cross the finish line. It’s just for fun.”

Alamo said it’s sometimes challenging to find the time to exercise, especially with four children and a full-time job, but he usually runs in the early morning with his dog, a husky named Jack. Jack and Alamo’s wife and children — including his 6-year-old daughter, Ariel — will join him for parts of the race. The plan is, he said, for the family to cross the finish line together sometime Monday evening. Also running in various stages of the race will be his wife, Chat, and his sons, Jude, 16, and twins Kyle and Karl, 15.

“The whole family will run the last mile or two together,” said Alamo. “It will be an interesting experience. We love this town and this is to support windjammer week.”

Alamo’s run, and the Lassis’ sailing voyage, will begin at the Rockport Marine Park on Pascal Avenue in Rockport, where they will depart at about 7 a.m. June 25. Alamo will run south on Route 1 before turning onto Route 90. He’ll rejoin Route 1 in Warren before making his final turn on Route 27 down the Boothbay peninsula. The Timberwinds will take whatever route the wind allows.

Alamo said the strength of the wind doesn’t make much difference for a runner, but it sure does for a windjammer.

“I’m hoping for a southwesterly wind,” he said.

Tassi said winning isn’t the point, though something in him hopes the schooner doesn’t lose.

“I hope we both end up coming into the harbor at the same time,” he said. “I hope it all evens out, but there’s no way of knowing until the day of sail.”

Cherie Scott of the Boothbay Harbor Region Chamber of Commerce, who is the festival’s project manager, said many of the traditional attractions, along with some new ones, will make the 50th installment of the festival bigger and better than ever. Windjammer Days is a family festival that this year will attract 12 windjammer ships and a pirate ship to Boothbay Harbor.

There also will be sailboat races, a golf tournament, an antique boat parade, a craft show and artist alley, lectures, live music, a boating treasure hunt and, according to Scott, a “real show-stopper of a parade,” which kicks off at 5 p.m. Wednesday, June 27.

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Christopher Cousins

Christopher Cousins has worked as a journalist in Maine for more than 15 years and covered state government for numerous media organizations before joining the Bangor Daily News in 2009.