Few people stumble into a lifelong calling the way Stackpole did. A descendant of a whaling family, he spent his early childhood on Nantucket, Massachusetts. His father, Edouard—an author of numerous books and monographs on whaling and Nantucket—moved the family to Mystic, Connecticut, in 1953 when he became director of Mystic Seaport Museum. Matthew grew up climbing and playing aboard the whaleship Charles W. Morgan, later working as a rigger at Mystic and crewing for five years on the topsail schooner Shenandoah. Those years introduced him to Martha’s Vineyard, which would remain an important place in his life.

In the early 1970s, Matthew and his wife Martha bought the 50-foot Concordia schooner Mya. Both schoolteachers at the time, they lived aboard during summers and operated Mya as a charter. His professional life has included serving as executive director of the Martha’s Vineyard Museum and president of Sail Martha’s Vineyard—organizations where he continues to contribute as an honorary director. He later returned to Mystic to help lead major fundraising and restoration work for the Charles W. Morgan, and today consults on the restoration of the historic schooner Ernestina-Morrissey while working with the Martha’s Vineyard Preservation Trust.

First Memory of Being on a Boat

My earliest clear memory is sailing a Beetle Cat called Curlew at Mystic Seaport. My father used that boat, and my twin brother Chris and I learned to sail on her. Those childhood days of learning to trim and tack together planted the roots of a lifelong love for small sailing craft.

First Boat I Owned

Our first boat was the 50-foot Concordia schooner Mya. Martha and I bought her in the early 1970s and, as teachers, spent our summers living aboard and running charters out of Vineyard Haven. Those 14 summers created a world of friendships, memories and formative experiences that remain central to my love of sailing.

Power or Sail—and Why

I’ve always favored sail. Sailing invites you to be part of the immediate environment, to work in harmony with wind and tide, and to enjoy a quiet that powerboats rarely offer. That connection to nature and the skillful teamwork involved are what I find most rewarding.

Your Current Boat

I currently own a 1976, 23-foot Stone Horse built by Edey and Duff in Mattapoisett, Massachusetts. It’s a fiberglass interpretation of a 1930s Crocker-designed wooden cutter and makes a very handy pocket cruiser—stable, responsive and perfect for short coastal cruises.

Favorite Boat You’ve Owned

It’s always easy to love the boat you have, but the Mya holds a special place as my first big boat and the one that opened so many doors. After Mya, a Herreshoff Fish Class sloop also brought me great joy; she was simple, elegant and a delight to sail.

Your Dream Boat

Dream boats change with life’s seasons. Mya was a dream in its time. Today, I find myself admiring a 28-foot Marconi sloop by Nat Benjamin—a well-built, classic small cruiser that would be my ideal if fortune ever allowed.

Most Rewarding Professional Experience

Being part of the team at Mystic Seaport that restored the Charles W. Morgan and sailed her on her “38th voyage” in 2014 was profoundly rewarding. For six and a half years we planned, fundraised, restored and ultimately sailed the ship—an effort that not only preserved an important artifact but also made history come alive for a new generation.

Scariest Adventure Aboard

On Shenandoah, during a wet, windy squall, the mainsheet ran away. Another crewmember and I were knocked down amidst the sheet as it raced through the blocks. Pinned in our foul-weather gear, we were spun helplessly—until a bight jammed in the block and saved us. It was a sobering reminder of how quickly conditions can turn and how fortunate we were that day.

Most Memorable Moment Aboard

Two moments stand out. One is the symbolic passage of the Charles W. Morgan through the Mystic drawbridge in May 2014. The other is sailing her up Vineyard Sound; both were surreal and deeply emotional experiences that underscored how impossible-seeming dreams can become reality.

Longest Time Spent Aboard

The longest continuous stretch was the many summers we lived on Mya—seasons full of distance, discovery and dockside life.

Favorite Destinations

Sailing the Elizabeth Islands and anchoring at Tarpaulin Cove is high on my list. I also cherish Brooklin, Maine, and the journey there—classic New England cruising that blends scenery, craftsmanship and hospitable harbors.

Favorite Nautical Books

I’m torn between John Masefield’s Jim Davis and Erskine Childers’ The Riddle of the Sands—both memorable works that capture elements of seamanship, adventure and atmosphere.

Favorite Nautical Cause

I support historic vessel restoration. Experiencing an authentic historic ship—being aboard, touching timbers that carried sailors of the past—creates a visceral link to history that no replica or exhibit can match. Restored vessels are living classrooms that inform and inspire future generations.

Favorite Quote About the Sea

George Adams, who was first mate on Shenandoah during my first year aboard, shared a line attributed to a Joseph Conrad character: “The only thing I care about when I’m on the ocean is the ocean not know that I’m there.” I’ve never found it in Conrad’s work, so I credit George with passing it on—a succinct expression of the humility the sea inspires.