For six decades, the wooden schooner Shenandoah has captivated passersby and served as a source of oceanic adventure for thousands of Island children.

Now in need of extensive repairs, much of which will be done using wood from Vineyard trees, the ship has caught the eye of a local film director who plans to tell the tale of her storied past and upcoming historic renovation in a feature-length documentary.

Over the next few years, director Catherine Stewart and her film crew of four, including producer Lloyd Fales, will follow Shenandoah’s 61st sailing season, the restoration process and the lives of her captains and sailors past and present. Ms. Stewart lives primarily in South Africa but spends summers at her home on West Chop.

The crew began filming in mid-December.

Directer Catherine Stewart and producer Lloyd Fales.

“It’s like we’ll be tracking the death and rebirth of this unique treasure that’s so iconic to Martha’s Vineyard,” said Ms. Stewart. “It just feels like there’s a real story here.”

Starring in the film is 91-year-old Capt. Robert S. Douglas, Shenandoah’s designer and former owner. Since sailing into Vineyard Haven harbor in 1964, Captain Douglas has been a living symbol of the Island’s wooden boat building industry and an inspiration and mentor to young mariners.

Operated originally as a charter vessel, Shenandoah was later transformed by Captain Douglas into a seafaring classroom for Island students, taking them out for week-long overnight sailing excursions.

“Bob Douglas said to me that even from the beginning, when kids came onto the boat, they would just be in tears when they left it, saying, ‘This has been the best time of my life,’” said Ms. Stewart. “His job was literally to give students the thrill of a lifetime.”

Captain Douglas retired from sailing in 2020 after a 56-year career, and donated Shenandoah to the Martha’s Vineyard Ocean Academy (formerly the Foundation for Underway Experiential Learning), a nonprofit that continues to take hundreds of children ages eight to 17 on the vessel each year.

Capt. Robert Douglas and Nat Benjamin chat during filming. — Ray Ewing

It was the Academy’s co-founders, Ian Ridgeway and Casey Blum (both of whom sailed on the Shenandoah as kids), who shared the ship’s origin story with Ms. Stewart and inspired her to film a documentary.

“Catherine came out on the boat last summer for a swim with her mother and she loved it,” said Mr. Ridgeway. “We began telling her about our programs and the ship’s story and she knew she wanted to tell it.”

But the Academy’s unique renovation plans for Shenandoah are what really convinced Ms. Stewart to pick up her camera, added Mr. Ridgeway.

With the help of Sheriff’s Meadow Foundation president Adam Moore, the ship’s rig, which needs a full replacement, will be partially built using pitch pines already harvested from Phillips Preserve in Vineyard Haven. The trees were logged earlier this fall after the area became infected with invasive southern pine beetles. They will be milled on-Island and to spec primarily for Shenandoah’s decking.

“I had already agreed to help Ian and Casey get the wood, and then in the interim we had this southern pine beetle outbreak and had to cut a fair amount on the preserve anyway,” said Mr. Moore. “They’re all stacked up and ready to be used.”

Adam Moore and Ian Ridgeway at Phillips Preserve. — Ray Ewing

Mr. Moore said he knows firsthand how valuable a week on Shenandoah can be for both Island children and adults. All four of his kids sailed under Captain Douglas, and his wife, Melissa Moore, was an avid chaperon.

“How many people get to spend a week aboard a schooner and listen to the captain tell his stories and learn about the sea and all about knots and so forth?” said Mr. Moore. “It was such a rewarding experience for all of them.”

For other parts of the ship, including the hull and masts, the Academy plans to use white pines from New Hampshire forests, a process that Ms. Stewart said she is especially excited to document.

“They’re going to cut them down and then travel them down special logging roads that are hundreds of years old,” she said. “Then, they’re going to travel them by river and sea.... In my mind’s eye, I immediately saw how beautiful that would be to film. It’s just not something that’s done these days.”

But before its makeover, Shenandoah will spend one last summer on the water in her current form.

Setting up a shot in the Five Corners Shipyard — Ray Ewing

In the meantime, Ms. Stewart and her crew are focusing the camera on the ship’s sailors and some of the Island’s most prominent nautical figures. Their first day on set, Dec. 18, was spent in the Five Corners Shipyard filming a conversation between Captain Douglas and Nat Benjamin, co-owner of Gannon and Benjamin Marine Railway and longtime wooden boat builder.

Mr. Ridgeway and Ms. Blum also spent some time in front of the camera.

“Ian actually had his acting debut in Almost Famous as an extra,” said Ms. Blum.

“No, actually, I wasn’t an extra,” corrected Mr. Ridgeway. “I had a speaking line... that got cut.”

Now on a filming hiatus, the team will return in the spring when the Academy starts to ready the ship for spring and summer voyages.

“And when we come back, we’d love to meet and film more people who have stories of Shenandoah,” said Ms. Stewart. “This is a community project. That is the true beauty of it.”

To learn more about the documentary or share a story about Shenandoah, contact film producer Lloyd Fales at For more information about Shenandoah’s renovations, visit