In Oakcliff Sailing Center’s main building near Oyster Bay Harbor on New York’s Long Island, a half-dozen employees, students and volunteers are bustling around the office, organizing upcoming regattas and other events. In the adjacent maintenance shop, a staffer is finishing a fiberglass repair to the bow of a catamaran shattered in a collision. Upstairs in a new dormitory, eight young sailors are holding a “debrief” on how they might have performed better in a race in Newport, Rhode Island, the previous weekend. Across the street in Oakcliff’s boatyard, another staffer rolls touch-up paint onto a 40-foot sloop.
If we’re lucky, most of us stumble into doing something we enjoy. Few of us are born to a purpose, as Matthew Stackpole seems to be. A descendant of a whaling family, he spent the first seven years of his life on Nantucket, Massachusetts. His father, Edouard — the author of 28 books and monographs on whaling and Nantucket — moved the family to Mystic, Connecticut, in 1953 when he was made director of Mystic Seaport Museum. Stackpole grew up playing aboard the whaleship Charles W. Morgan, then worked as a rigger at Mystic. He spent five years crewing on the topsail schooner Shenandoah and fell in love with Martha’s Vineyard. In the early 1970s, Matthew and his wife, Martha, bought the 50-foot Concordia schooner Mya. They were schoolteachers at the time, so they lived aboard in the summer and ran charters. Stackpole was also the executive director of the Martha’s Vineyard Museum and president of Sail Martha’s Vineyard, where he is still an honorary director.
It seemed somewhat inevitable, though, that he would eventually be called home to Mystic and the Charles W. Morgan. Stackpole was the major gifts officer on the team — leading the fundraising effort for the historic ship’s restoration — as well as Mystic’s designated Morgan expert in the years leading up to her 38th voyage in 2014. Now he works with the Martha’s Vineyard Preservation Trust and as a consultant on the restoration of the historic schooner Ernestina-Morrissey.
If the Ernestina-Morrisey wasn’t considered a lucky ship before, she sure is now.
First memory of being on a boat: The first boat I remember sailing on was a beetle cat called Curlew, a sweet boat, at Mystic Seaport, which my dad used. My twin brother Chris and I learned to sail, and enjoyed arguing with each other, on her.
First boat you owned: The 50-foot Concordia schooner Mya. My wife, Martha, and I bought her in the early ’70s, and as we were both schoolteachers, we lived on and ran her as a charter business for 14 summers out of Vineyard Haven on Martha’s Vineyard.
In general, power or sail and why: I have always been on or had sailboats, so that’s clearly my preference. The concept of being a part of the immediate environment, which requires you work in harmony with it to get to wherever you want to go, and the quiet are most pleasing to me.
Your current boat: A 1976 23-foot Stone Horse. It was built by Edey and Duff in Mattapoisett, Massachusetts, and is a fiberglass copy of a wooden Crocker-designed cutter built in the 1930s. It’s a handy pocket cruiser.
Favorite boat you’ve owned: I suspect we all have to love the boat we currently have, but it’s hard not to love one’s first boat. We were so lucky to own and sail Mya, a truly beautiful and fine sailing vessel that transported us into a wonderful world of friends and experiences. That said, we subsequently had a Herreshoff Fish Class sloop that was a joy to sail.
Your dream boat: That depends on where you are in your life. Mya was a dream boat. However, there is a 28-foot Marconi sloop designed by Nat Benjamin I covet; that would be a perfect dream if someone wanted to give it to me!
Most rewarding professional experience: Being a small part of the amazing, talented and passionate team at Mystic Seaport that restored the Charles W. Morgan, and planned and sailed her on her “38th voyage” in 2014. Every aspect of the six and a half years I was part of that project was incredibly stimulating and satisfying. We not only saved history — we made history, too.
Scariest adventure aboard: When the mainsheet got away from us in a windy, wet squall on Shenandoah. I was knocked over, along with another crewmember, amidst the mainsheet as it was racing out through the block. We were in full foul-weather gear and were like two Galapagos Island turtles on their backs being spun around. Fate intervened when a bight in the sheet jammed in the block, saving us.
Most memorable experience aboard: It’s a tie between the symbolic moment the Morgan went out through the Mystic drawbridge in May 2014 and, for all sorts of personal reasons, sailing up Vineyard Sound on her. In many ways it was a surreal experience that still takes my breath away when I think of it. Impossible dreams do sometimes come true!
Longest time you’ve spent aboard: The summers we lived on board Mya
Favorite destination so far: Sailing along the Elizabeth Islands and the anchorage at Tarpaulin Cove top my list, closely followed by both Brooklin, Maine, and the journey there.
Favorite nautical book: Another tie: John Masefield’s Jim Davis and Erskine Childers’ The Riddle of The Sands
Favorite nautical cause you support and why: Historic vessel restoration. I’ve seen the power that the authentic — the real thing — has to make history come alive; nothing can duplicate it. Something one can be on and/or touch is a magic portal that allows history, and the people who made it, to come to life and do its important job of informing the future.
Favorite quote about the sea: George Adams, who was the First Mate on Shenandoah my first year aboard, told me this quote, which he said came from a character in one of Joseph Conrad’s books. I’ve never come across it, so I now attribute it to George: “The only thing I care about when I’m on the ocean is the ocean not know that I’m there.”
This article originally appeared in the October 2015 issue.
Stewart Workman avoided the urge to hunker down when business got tough. Now that’s paying off.
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If you’ve ever been to Newport, Rhode Island, or to any of the world’s great classic yacht regattas, you have seen them: the stunning — and winning — W-Class sailing yachts. In 1997, Boston real estate developer and passionate sailor Donald Tofias approached designer Joel White, of Brooklin Boatyard in Maine, with an idea to revive one-design match racing and spirit-of-tradition yachting.
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