The Island’s iconic schooner Shenandoah will be headed out of Vineyard Haven harbor this weekend as the ship owners and a Connecticut nonprofit consider a transfer of ownership.
While details of a potential deal are still being hammered out, the Martha’s Vineyard Ocean Academy on Saturday will be sailing the group’s 63-year-old vessel to Mystic, where it will be docked at the Mystic Nautical Heritage Society for the winter.
Once in Connecticut, the nautical heritage society will stabilize the aging topsail schooner and conduct a survey to tally up the needs of the vessel, the Ocean Academy, nautical heritage society and Island supporters said Friday.
That survey will help chart the course for the future of the beloved vessel and determine if work can be done to keep the Shenandoah in the water.
“We’re going to host her at our dock in Mystic,” said nautical heritage society president Geoffrey Jones. “And then we’ve got to figure out what happens next.”
Designed and captained by Robert Douglas, the founder of The Black Dog, the Shenandoah was a floating classroom that schooled generations of Island children in the ways of sailing.
In 2020, Captain Douglas handed the vessel over to the Ocean Academy, which carried on the educational mission. Last summer, the organization announced that it planned to retire the Shenandoah, saying it became untenable to continue pouring time and money into the wooden boat while also continuing programming.
After the schooner made its last trip with Chilmark School students last month, one of the biggest looming questions was what would happen to the boat in retirement as the Ocean Academy raises money to build a new boat.
While there still isn’t an exact answer to that, Shenandoah co-captain and Ocean Academy co-founder Casey Blum said the move to Mystic helps buy the vessel time.
“I think the hope on both sides is, of course, the preservation of Shenandoah,” she said. “Geoff has a long history with the boat and is offering to help give the boat some more time… There’s really no downsides to that.”
Mr. Jones’ organization has helped preserve other historic schooners, including the 100-plus-year-old Roseway and Alvei. This project was also personal for Mr. Jones, who got his first paying job on the water in 1979 when he did the dishes on the Shenandoah.
Along with Mr. Jones, a group of Islanders is working to help keep the vessel going, including the Douglas family and Island boatbuilders Gary and Kristi Maynard.
“We call ourselves Save Shenandoah but we don’t have an official name,” said Mr. Maynard.
Mr. Maynard was a galley boy on the Shenandoah in 1979 and is childhood friends with Mr. Jones. Mr. Maynard would go on to rise through the ranks until he made mate in 1986, and then got involved in carpentry and boat restoration.
These types of stories were a common refrain among the people around the deal, and all said that the boat represents a piece of Island culture.
“Shenandoah is just part of our lives and is beloved,” said Ms. Maynard. “We feel that she has some more life in her.”
The cost of keeping Shenandoah seaworthy was one of the main reasons the Ocean Academy didn’t feel it was feasible to continue operating the vessel. After the nonprofit took ownership of the boat in 2020, the organization put about $1 million into rebuilding the stern.
But continuing to use it to take kids out on the water would likely have needed a total rebuild, which could have cost upwards of $10 million, according to Ms. Blum.
“The Coast Guard has outlined significant work they would like done, which isn’t feasible for Martha’s Vineyard Ocean Academy to take on,” she said.
Keeping the Shenandoah in Vineyard Haven harbor as the Ocean Academy works to build a new vessel, Shenandoah II, was also less than ideal.
“It is expensive to keep it on the mooring in Vineyard haven and there’s cost with keeping insurance,” Ms. Blum said.
While in Mystic, the committee to save the Shenandoah and the nautical heritage society will look at repairing the leaky decks, and all the parties hope to have it open and available to the public. Mystic is one of the major wooden boat ports in New England and the vessel will be right alongside the city’s maritime museum.
“What’s appealing to us is that the boat is going to be fully rigged and dockside in Mystic and the public will have access to it,” said Ms. Blum.
While negotiations continue for the ownership transfer, Ms. Maynard said she is reaching out to people who would be potentially interested in stewarding the vessel for the long-term. The nautical heritage society will give the vessel a safe harbor and help with the next steps, but the ultimate goal is to pair her with another owner after that.
“We act kind of like match.com between old wooden boats and people crazy enough to take them on as projects,” said Mr. Jones.
Ms. Maynard is hoping to find people who want to see Shenandoah continue on, whether that be as a seaworthy vessel, a floating museum or something else.
“We really don’t know yet, but we are open to all possibilities,” she said.
Though it was built in 1963, the ship resembles a mid-19th century sailing vessel, and great effort was taken by Captain Douglas, who died in 2025, to keep its historic origins.
It was only the second commercial sailing ship built in the U.S. without an engine in the United States since 1921.
“She’s the most beautiful topsail schooner in the world,” Ms. Maynard said. “When she is sailing and you see her rounding West Chop your jaw drops.”
The boat will be pulled by a tug out of Vineyard Haven Saturday morning, before taking advantage of the tide and favorable weather for the 80-mile sail to Mystic, said Ian Ridgeway, who captains the Shenandoah founded the Ocean Academy with his partner Ms. Blum.
Mr. Ridgeway’s crew, Ms. Maynard and others will be on the vessel for what may be the Ocean Academy’s last sail as owner of the vessel. Looking back on his time at the helm, Mr. Ridgeway said he was proud of the work that went to keeping the vessel afloat and getting it this far.
“Caring for a 63-year-old wooden boat is a serious undertaking and we have been so proud of the six years of stewardship under Martha’s Vineyard Ocean Academy,” he said.
The descendants of Captain Douglas were grateful to everyone who has played a role in setting up the next chapter of the Shenandoah, even if the future is still unclear.
“I have wonderful memories of visiting Mystic with my father aboard Shenandoah when I was young and I am sure Dad would approve of this new chapter and be very happy to see his Shenandoah in Mystic, Connecticut,” said the captain’s son Rob Douglas Jr.
So great to hear. I worked on Shenandoah in the late 70s. Capt. Douglas created a boat of such sweet lines and full rig. He set a tone of living that touched many of us. This boat will always reflect all of this.
More generations may get to experience some parts of that understanding.