On a cool day in early May, Ian Ridgeway stepped off the dock by The Black Dog Tavern in Vineyard Haven and into a small skiff. He was headed out to Shenandoah, the 108-foot topsail schooner moored in the harbor, to check in on the work being done to prepare the ship for its last-ever season of sailing.
Robert Douglas, who designed and built the schooner in the early 1960s and captained it for fifty-six years, usually liked to keep his names simple. The boat Ridgeway was standing on was called Black Skiff. A short ways away was White Skiff. Douglas’s famous dog, seen on shirts all around the country, was named simply Black Dog. But Shenandoah got a more evocative title, named for a beloved sea chantey.
The ship itself was an anachronism even when it was built. It lacked many of the contemporary features other boats had at the time, including an engine, but passengers – many of whom have been school-aged children out for a transformative week at sea – haven’t been bothered. They’ve been happy to pitch in and crank the capstan or the windlass, both man-powered mechanisms on board. The galley’s charcoal stove worked well enough to make breakfast, lunch, and dinner for the groups of children who learned to sail, tie knots, and muster the courage to climb the rigging and jump into the ocean below. The ship’s kerosene lamps lit the main saloon well enough to see Douglas’s face as he regaled them with stories and songs in the evening.
It was a conscious choice to build an old-fashioned boat. “When you have too many systems on board, you spend more time fixing them than actually sailing,” Ridgeway said. In other words, Shenandoah had exactly what was needed and nothing more.
This low-tech experience away from land made an impact on generations of children, including Ridgeway and his partner in business and in life, Casey Blum. Ridgeway, who was born in Connecticut and grew up on Martha’s Vineyard, first sailed aboard Shenandoah in fifth grade. He was a boy with white-blond hair and a knack for climbing the rigging barefoot. Blum, who grew up in Georgia, first cautiously stepped aboard Shenandoah’s sister ship, Alabama, around the same age while visiting the Island. At first, she was worried the ship might capsize. It didn’t, and both of them kept returning season after season, building a love for the ships and a bond with Douglas.
Ridgeway and Blum went on to get their captain’s credentials: he has a 500-ton master’s license and she a 100-ton master’s license. In 2017, they started a nonprofit, then called Foundation for Underway Experiential Learning, now called Martha’s Vineyard Ocean Academy (MVOA). Its goal is to carry on the mission that Douglas started: to change lives through experiences at sea. In 2020, when Douglas was ready to let go of Shenandoah’s helm, he donated the boat to their organization.
For several years, Ridgeway and Blum lovingly maintained and repaired the ship. But, eventually, the work needed to restore the boat became untenable. In the technical sense, it had been totaled: the cost of repairing it would be more than building a new one. So, that’s what they decided to do. Fundraising is now underway to build a new vessel. The original Shenandoah will retire from sailing after this summer.
It’s a momentous change for the Island. Ridgeway estimated that at least 17,000 people have sailed aboard Shenandoah over the years. Even those who have never set foot on its well-worn deck are likely familiar with its striking black hull and tall masts, or have been transported by the sight of it clipping along at full sail like a traveler from a bygone era. When moored, the ship has been an iconic sentinel greeting and bidding farewell to all who enter or leave Vineyard Haven Harbor.
But Douglas, who died in 2025, knew this day would eventually come, and he’d drawn up plans for a new schooner in the early 1970s. In the last years of his life, he collaborated with Ridgeway on some minor adjustments. “It’s a perfect boat and it should be built,” Douglas said in a trailer for a still-in-progress documentary about the ship.
Although the cabins and deck will still be made of wood, the hull of the new boat will be made of steel. This material will be stronger, longer-lasting, and more cost-effective to construct and maintain. It will allow them to travel farther, and for longer. A few other changes are planned too. The bunk rooms have been redesigned so that kids won’t have to climb over each other as much. The galley will be above deck, along with a small workshop for repairs and projects, in a deck house.
The deck house will be small, said Ridgeway, but just big enough. “There’s a quote I like from Robin Lee Graham who sailed around the world at age sixteen. ‘At sea, I learned how little a person needs, not how much.’”
This next iteration will carry on the same less-is-more, human-powered ethos as Shenandoah. And what will the new ship be called?
“I can’t tell you,” Ridgeway said with a smile.
Douglas had insisted that the new boat’s name be kept a secret until they’d signed a contract with the shipyard that would build it, Ridgeway explained. While I considered the idea of a question with no answer, Ridgeway pulled Black Skiff's ripcord once, twice, three times. Finally, the engine started and we were headed out.
•••
When the man who dreamed up Shenandoah was still a boy of fifteen, he visited the Island for the first time. It was 1947 and Douglas had learned to sail on Lake Michigan, near his home in Lake Forest, Illinois. His family had a couple of sailboats in Vineyard waters, but at the time, young Douglas had his eyes on the sky. He trained at the now-gone Oak Bluffs airport and flew solo for the first time at age seventeen, according to My Shenandoah: The Story of Captain Robert S. Douglas and His Schooner (Tilbury House Publishers, 2022) by Doug Cabral, a friend of Douglas’s.
After a few years in the Air Force, being airborne began to feel strange and unnatural and Douglas came back down to earth. One of his early boats was Ayuthia, a twenty-ton ketch. He sailed on others and began to envision plans for the ship that would become Shenandoah.
The boat was built in 1963 and launched in 1964 in South Bristol, Maine. Moored in the harbor, Shenandoah has been “a visible sign of what sailing vessels that plied the waters around the Vineyard and Nantucket used to look like,” said Bow Van Riper, historian and research librarian at the Martha’s Vineyard Museum in Vineyard Haven.
On any given day in the nineteenth century, there might be one hundred ships ranging from “smaller sloops of twenty or thirty feet, all the way up to schooners the size of Shenandoah and beyond,” Van Riper said.
More than a visual reminder of this once-packed port, the ship also served as a way to experience the past, he said. “Most of us, most of the time, encounter history in the pages of books, or in the history teacher you had in school who was like something out of Ferris Bueller’s Day Off.” However, stepping onto Shenandoah “gives you the opportunity to experience history through all your senses, through the feel of the rope in your hands, the smell of the wood, the feeling of the wind and the sun on your face, and the way the shadows of the sails fall over the deck,” Van Riper said. “That gives you something that no book, no movie, no lecture – no matter how good it is – can really recreate.”
Shenandoah was like a piece of living history and so, in some ways, was Douglas, said Nat Benjamin, who started Gannon & Benjamin Marine Railway in Vineyard Haven with Ross Gannon.
“He was kind of a nineteenth-century guy,” Benjamin said. “He was upholding these wonderful traditions, not just in design and construction, but in sailing and in living.” He cared about craftsmanship and upkeep and doing things the right way, even if it took longer.
Benjamin and his wife, Pam, first arrived to the Vineyard by water, sailing into Vineyard Haven Harbor in 1972, long after the harbor bustled with sloops and schooners. “We were in our early twenties, and the first boat we saw was the tall ship Shenandoah.” She made an impression on both of them.
“It was a beautiful harbor, but there wasn’t much going on” at the time, Benjamin said. There were a handful of wooden boats in mediocre condition. “But then there was the flagship, the Shenandoah, which was this shining citadel on the hill.”
Over the years, interest in Shenandoah and wooden boatbuilding increased. Locals couldn’t always afford a new boat, he said, but they could find an old one to repair. “If they were willing and industrious, they could fix it up and have themselves a pretty good boat.”
That energy led to the creation of the Gannon & Benjamin Marine Railway in 1980. Today, it is an internationally renowned center for expertly crafted wooden vessels.
Since he arrived in the seventies, Benjamin has seen the Vineyard Haven waterfront continue to evolve. “This is one of the few harbors in the United States that has really changed for the better,” he said with a laugh. “The way the harbor is run, the new harbormasters are really good. The docks are better, they’ve been rebuilt. This harbor works together. If someone’s in trouble, we all go and help out.”
The changing harbor has been visited by countless boats over the years, but perhaps few have had a greater impact in the last century than Douglas’s schooner. “Shenandoah was the catalyst that got this terrific harbor of ours involved in the wooden boat,” Benjamin said.
•••
Black Skiff puttered to a stop beside Shenandoah’s massive hull and Ridgeway and I climbed aboard. He apologized for the current state of the ship. Everywhere, patches of paint had been sanded down, and everything was coated with dust. A mast lay on its side; the flagpole, or very top of the mast, had been sawed off.
“Once you cut down a tree, it begins to die,” he said. Each year, Shenandoah requires weeks of maintenance work in order to get the boat in shipshape. There’s also a never-ending fight against the inevitable march of rot. The crew had cut off the rotten wood at the top of the mast and would replace it before setting sail.
Beyond upkeep and sailing, the crew is also tasked with mentorship. The group is often comprised of young adults, some with sailing experience, some with experiential education experience, and some with neither.
“It’s the most adventure you can have,” Ridgeway said. “And you have to like working with kids.”
Islander Kyra Whalen brought her previous experience as a teaching assistant at the Chilmark School on board as a crew member during the summers of 2023 and 2024. “The trips ran from Monday to Saturday,” she recalled, “and often the boat comes back into the Vineyard Haven Harbor on Friday evening.” She loved “the feeling of sailing back into the harbor...the sun is setting, and there are other boats sailing around you. It’s this very wonderful experience,” she said.
Yet at its core these trips are mission-driven. Kids are expected to be present and to help out. They’re treated like young members of the crew. “We need this opportunity for our youth to get off their screens and have these real and sometimes difficult, uncomfortable, and challenging experiences that they can grow from,” said Ridgeway.
MVOA is “a lot more than a recreational program,” said Blum. “A recreational program is concerned with questions like ‘How do people feel about the experience. Did they have fun?’ And we define ourselves as a developmental program. What that means is we are concerned not only with how our participants feel, but also how they think and how they behave.”
Blum, a social worker, is serious about MVOA’s impact and outcomes. She developed a curriculum that has been used by other programs on tall ships throughout the country. Her research, using the Shenandoah model as a case study, has been published in the Journal of Experiential Education.
With MVOA, Blum is instead asking questions such as: “What happens when you get these kids in this environment? How do they treat each other? How do they show up with empathy and respect? How do they contribute when they’re part of a community?”
“The fact that there’s inherent risk in the environment is what makes it authentic,” she added, “and even kids at a young age can sense that authenticity.”
At the end of every trip, Blum makes a point of gathering the children into a circle and asking what about the experience they were most grateful for. Answers range from the quality of the food (“I think the kids always expect that the food is going to be terrible,” she laughed) to the time spent connecting to others. Some say, “I’m grateful I was able to make friends without my phone. I didn’t think that was possible for me,” Blum recounted.
Hearing comments like those, “you realize, wow, this actually had a massive impact on how this person views themself in the world.”
Blum and Ridgeway would love to find a way to preserve Shenandoah, the site of all those moments that have shown people who they are. “The best way to do that is to pull it out of the water and put a roof over it,” Ridgeway said. He would like visitors to be able to climb aboard and run their hands along the railing, feel what it’s like to lie in the two-foot-wide bunks, and sit at the dining tables that are built to rock along with the waves.
As Ridgeway and I conducted our own tour, we climbed the ladder down into the captain’s quarters at the stern of the boat. Taped to the wall was a picture of Douglas, working on another boat, a smile on his face. On one of the bunks were two copies of the program from his memorial service. Saying goodbye to Douglas was hard. Saying goodbye to Shenandoah – at least the version that sails out from the Island – will also be difficult, Ridgeway said.
“This is the site of the most important parts of my life. If there wasn’t something dangling in front of me that was very exciting, more exciting even, I think it would be really sad and hard.”
At the time of publication, MVOA has raised a total of $3.8 million for Shenandoah II, as they’re currently calling it, which is 61 percent of their overall goal. But, for both Blum and Ridgeway, the real payoff of all the fundraising and boatbuilding will be the look of confidence in the kids’ eyes after they work together to raise the new topsail or jump from the new rigging into the water.
“What makes it so magical is the experience that it will provide for the children whose lives it changes,” Blum said. “The fact that another five or six generations of Islanders could go sailing on Shenandoah II is what will make the soul of the boat come to life.”
