Farewell, Shenandoah

The sun set as Islanders gathered for a potluck at the Black Dog Wharf docks in Vineyard Haven to honor Shenandoah, a one-of-a-kind, 108-foot wooden topsail schooner, where thousands of the Island’s youth have embarked on week-long adventures to be educated in hands-on maritime work. 

At the potluck on Saturday evening, with Shenandoah docked along the wharf, families, friends, crew members, and stakeholders gathered to remember its impact on the local community. 

The event on Saturday was planned in concert with Gannon and Benjamin Marine Railway, which was celebrating its annual Pat West gaff-rig and schooner race, a late summer favorite sailboat race on the local waterfront. 

Rose Guerrin and Buck Shanks performed on Shenandoah from 5 pm until 7 pm next to the Black Dog Wharf, where food and drinks were offered, and Dock Street Fight Club later played at the Gannon and Benjamin shop, where the fun continued into the night.

Ian Ridgeway, captain of Shenandoah for the past six years, recalled his own experience on the vessel in a speech to the crowd. 

Ridgeway said he first boarded Shenandoah when he was 11 years old, when he was a student at the Tisbury School. 

“I was a high energy kid that did not thrive in a classroom setting like many young boys, and I came out on Shenandoah and was immediately enamored by everything she offered to me,” Ridgeway said. “It was a place where my energy was valuable, where there’s always something to do, always something to learn, a giant jungle gym that I could climb around on as much as I wanted.”

Since 2020, Ridgeway, now 42, alongside Casey Blum, has co-captained Shenandoah and co-directed the Martha’s Vineyard Ocean Academy, the organization that purchased the ship from Capt. Robert S. Douglas, who designed the ship in 1964 and was its captain for 56 years. 

Ridgeway recalled learning from Douglas, who died April 23, 2025.

“[He was] an incredible mentor who took me under his wing and taught me so much about life and how to lead,” Ridgeway said. 

More than 15,000 students from all of the Islands’ schools have spent week-long trips on the vessel, and Ridgeway said for many Islanders an excursion on Shenandoah is considered a “rite of passage” through the Island’s education system. 

Ridgeway said students who go on Shenandoah come back “taller, prouder, more resilient, and more ready to take on life’s challenges.” 

“The exact ingredients that kids today need so much,” he said. 

Blum, who spoke first at the potluck, thanked the crowd for supporting her and Ridgeway’s stewardship of the vessel over the past six years. 

“I’m really grateful to all of you for coming tonight and being here to celebrate Shenandoah and her remarkable history on this Island,” Blum said.

Blum introduced Matthew Stackpole, who was the third-ever first mate for Douglas on Shenandoah.

Stackpole said the vessel was a “portal to another world, another life, another set of values” for the Vineyard community and all who sailed it. 

“She has impacted so many lives on this Island and has been both a way to understand and view the past, but also a transition to the future,” he said.

Stackpole called the vessel “a place where you don’t have cellphones or noise, you just have each other, and you have to learn how to collaborate.”  

Jerry Goodale, one of the original crew members, attended the celebration. He was a deckhand and then a boatswain from 1964 to 1966. 

“She has been valuable,” Goodale said. “Sad to see her have to retire, but I understand.” 

Captains Ridgeway and Blum announced last summer that the 2026 season would be Shenandoah’s last as continued repairs aren’t financially practical anymore. The nonprofit is fundraising to build Shenandoah II and continue its maritime education programming for Island students.

Ridgeway said they have $900,000 left to raise before they can begin construction of the steel-hulled Shenandoah II, also designed by Douglas. Ridgeway said he expects it to cost about $9.85 million in total.

“I really hope you can all feel proud of what Shenandoah has done for this community and feel excited about the future because we’re going to sail this thing on into the future,” Ridgeway said.

After the speeches, Shenandoah’s crew fired off four cannons, which shook the docks and  hearts of all attendants. It was a last show of the strength the old schooner still carried, and the crew lowered her flags, symbolizing the retirement of the vessel.