Historic ferry built in 1911 finds temporary home in Greenport

Since mid-summer, the unmistakable wooden vessel Prudence has gotten more than a few curious glances in Greenport. The 64-foot boat, which hearkens back to the early 20th century, was hauled out in July and remains propped up at Greenport Yacht Yard.

“Everybody’s asking about it,” said Sean Gilligan, general manager of the yacht yard and Stirling Harbor Marina, both of which are now operated by Safe Harbor. “They want to make a bar out of it.”

So how did a century-old former steamer that once hosted private parties for Ted Kennedy end up in Greenport?

Built in 1911 in Boothbay Harbor, Maine, Prudence is one of only three “coastal steamers” still in operation, according to current owner Jonathan Wilkes. While it was converted to diesel power decades ago, likely in the 1960s, it has retained its original look. Mr. Wilkes captains the former ferry for Mystic Cruise Lines in Connecticut for catered events and parties.

“She’s full of history,” he said.

Mr. Gilligan said the yacht yard hauled Prudence out for a Coast Guard inspection. He said there are few places that can handle hauling out a wooden vessel of that size. Most boatyards would shy away from such a vessel, he said.

“We had the expertise to be able to help these people out,” he said.

Mr. Wilkes said the plan is to launch Prudence shortly after Labor Day, adding that it should return to service next year. He started a business chartering boats in the late ’00s after the market crash made it tough to sell boats as a broker, which he had been doing for nearly 20 years. He bought a 42-foot boat and began the business in Greenwich, Conn. He would soon realize he needed a bigger boat, and something with a little character and charm.

“I didn’t realize I was going to find something with such incredible history,” he said.

The top deck of Prudence. (Credit: Joe Werkmeister)

He bought Prudence at the end of 2012 and put it into service the following year, he said. He eventually moved the business to Mystic, Conn.

The vessel was christened Madeleine when it was built at Irving Reed Shipyard, according to a detailed account published in 2012 by the Wiscasset Newspaper in Maine. A fire in its boiler room damaged the vessel in 1920 and it was sold the following year to Island Navigation in Bristol, R.I., where it was renamed Prudence, according to the newspaper. For more than four decades, Prudence served as a ferry carrying not only people, but livestock, automobiles and freight.

Mr. Wilkes said the vessel would then become a boat used to tour the Kennedy compound from Nantucket Sound.

A family who owned a gas station in Hyannisport, Mass., had started doing tours of the compound by bus before the Secret Service put a stop to it, Mr. Wilkes said. So they decided to buy a boat. It was in 1962 that brothers Richard and Robert Scudder bought Prudence, according to the Wiscasset Newspaper.

“They grew one of the bigger passenger vessel companies in New England,” said Steve Pagels, who owned Prudence briefly before Mr. Wilkes. The Scudders launched Hyannis Harbor Tours, which became Hy-Line Cruises.

Mr. Pagels said he acquired Prudence shortly after it celebrated its 100th birthday.

“It’s quite a historic vessel,” he said. “There’s not many original old-style wooden ferries around.”

Steam ferries like Prudence would have been common back when the boat was first built, he said.

The propeller and wooden rudder. (Credit: Joe Werkmeister)

A replica of Prudence called Patience was built in 1982 in Stonington, Maine. It’s a slightly larger version, at 72 feet. That boat also began by providing tours of the Kennedy compound. Mr. Wilkes bought Patience as well in 2015. Patience is also currently sidelined and Mr. Wilkes said they are operating their 74-foot schooner Mystic Pearl this summer.

Prudence was lucky to ever make its 30-year anniversary. The boat managed to survive the Great Hurricane of 1938, Mr. Wilkes said, and the day after the storm, was found floating free in Narragansett Bay with the piers it had been tied to dragging behind.

When it comes to driving Prudence, Mr. Wilkes said, that job falls strictly to him.

“I haven’t met anyone else who can drive Prudence,” he said.

The vessel has a rope steering system, manual shift and manual throttle, he said.

Mr. Wilkes typically has two crew members — plus additional hands when the boat is filled for an event. He said they’ve been working on Prudence for about 18 months now.

“It’s been a real honor having her,” he said. “I invested a lot into her. By next spring she’ll be done and at that point she’ll be in the best shape she’s been in in over 30 years. Once we get her there, she’s good for a long time again.”

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