PROVINCETOWN — The year 2020 will see the 19th annual Great Provincetown Schooner Regatta, starting on Labor Day and running for four days, as long as somebody steps forward to take charge of organizing the event. Planning usually gets underway in winter. But after nine years at the helm, Cheryl Andrews says she is stepping down.
This is a familiar situation: the regatta has been a sort of dearly loved orphan ever since it was born in 2002. White knight organizers have saved the event on at least two other occasions, and the local sailing community is hoping that someone will come forward once again to keep the regatta afloat.
The Great Provincetown Schooner Regatta was the brainchild of charismatic captain John Bennett, who took his schooner Hindu to the Gloucester Schooner Festival every Labor Day weekend and wanted to invite his fellow captains back to the magnificent harbor of Provincetown for more races.
“John had sold everyone on this vision, and then he suddenly died that June of 2002, just three months before the first regatta,” said Andrews, chair of the regatta from 2011 to 2019. “A lot of people stepped in to help make it happen that year.”
Don Murphy became the lead organizer for the regatta, but he was running his main projects, the Provincetown Portuguese Festival and the Blessing of the Fleet, as well. “Those are huge events,” said Andrews, “and in 2007 Don said he couldn’t be the lead on the regatta anymore. We almost didn’t have one that year.”
Andrews said she remembered a big headline in the Banner that said, “Searching for a new commodore.”
“A couple of guys from out of town who were summer residents took it over, and they did an amazing job,” she added.
Ken DeGregorio and Cooper Ray were those guys. They ran the regatta for three years before moving back to Los Angeles full time, and during their tenure the event grew to include a schooner race from Gloucester to Provincetown on Tuesday in addition to the Long Point races in Provincetown Harbor on Thursday.
The next director, Charlotte Walker, added some races for smaller boats on Wednesday, and between the various races and the many classes of boat in each race there were dozens of trophies to give away at the post-race parties.
“One of the really special things about this event, you have these magnificent schooners, 100- foot boats, and they also allow smaller yachts in the same race,” said Andrews. “You’re tacking around Wood End buoy, and all of a sudden the Roseway, this 115-foot treasure, is coming up alongside you. As a boat owner, it’s just a blast. There’s nothing like it in the country.”
Getting the Schooners
“The challenge with the regatta is getting the schooners here,” said Murphy. “There are a lot of people in town who can lay out a race — it’s fun, you’re with your friends on the water. That part is great.
“The revenue model for the bigger schooners has changed though,” Murphy continued. “They can’t just make an appearance because they want to be here — they need to be doing charters, or they need ticket sales, and the financial side of it for them is much more complicated. And you can’t have a schooner race without schooners!”
Ron Robillard of the Provincetown Yacht Club confirmed that the schooner side of the equation is challenging. “We feel like we could run the Thursday Long Point race,” said Robillard, “but
recruiting the schooners, the whole project out of Gloucester — there’s a lot involved in the regatta beyond races. We don’t feel prepared to take that on.”
Andrews and Susan Avellar co-chaired the regatta after Walker stepped down. After a few years Avellar resigned as co-chair so she could focus on racing, and after nine years as chair, Andrews is retiring. A former Provincetown select board member, she has announced her intention to run for county commissioner next year.
“It’s the off-the-water activity beforehand, the organizational and financial work, that the regatta depends on,” said Murphy. “You gotta have the interest in racing and the love for sailboats, and the time. It’s a big challenge. Putting a model together — a financial model that can get these schooners here — it isn’t clear to me.
“I want to be encouraging, but I don’t know if the event is going to happen or not,” Murphy added. “These events happen because people believe in them and they want to see them. It won’t happen unless people volunteer to make it happen.”
“I remember the last time this happened,” said Avellar. “It was in the paper just like this, and we were talking about it in front of Wired Puppy, and that’s where we found Kenny, sitting on a bench. That’s really how we found him.”
“Kenny was fantastic — he had passion and energy, great contacts, he had style, and he walked the walk,” said Andrews. “He dedicated a lot of energy to make the regatta happen.”
