The Shenandoah first arrived in Vineyard Haven harbor in 1964. This Friday, the iconic topsail schooner will return to the harbor on its final voyage, sailing home with a group of Chilmark school students who have spent the week living aboard the ship.

Shenandoah will depart Tarpaulin Cove on Naushon around noon on Friday, and boats of every kind are invited to accompany her home in a parade of sail, kicking off a weekend of celebrations. The boat is to be retired after 63 summers of service, with plans to build a new vessel to continue its seafaring and educational legacy.

“Certainly the Shenandoah is a special ship,” said Marta Van Ranst, a volunteer with the Martha’s Vineyard Ocean Academy. “There’s no other ship like her.”

The Martha’s Vineyard Ocean Academy is an educational nonprofit that has owned and operated the Shenandoah since 2020, when Capt. Robert Douglas, the founder of the Black Dog, gifted the vessel to the organization.

Casey Blum and Ian Ridgeway, captains and co-founders of the Ocean Academy, have both been involved with the Shenandoah since the 1990s, when they set sail with her as Island students. Their decades-long connection to the Shenandoah inspired them to carry the maritime educational mission forward, Ms. Van Ranst said.

Generations of Island students have learned real-life skills aboard the ship. — Tim Johnson

“There’s no phones, no computers allowed during those voyages with the intention of helping kids whose lives are so surrounded by that…They get to learn what it is to be on your own, and responsible in a group setting, and all the things that are important to growing up as a grounded, present person,” Ms. Van Ranst said.

The mission continued this past week, when on Monday the Shenandoah set sail with a group of fifth grade students from the Chilmark School.

“It’s the traditional kickoff to the Chilmark School year to send out a group of students on Shenandoah,” Ms. Van Ranst said. “They will be sailing back from Tarpaulin Cove [on Friday] and we’ve invited anyone with a boat who’d like to join them in a parade back to Vineyard Haven harbor.”

On Saturday morning, the students will disembark, and the ship will dock at the Black Dog Wharf for Saturday’s festivities, which include a community potluck beginning at 5 p.m.

“Our goal is to have a toast to the ship around sunset when we’ll be firing the cannons for the final time at 6:45.,” Ms. Van Ranst said.

To wrap up the weekend, the Shenandoah will remain open Sunday for anyone who wants to say goodbye. Open boat tours will last from 11 a.m. to 5 p.m.

Current captains Casey Blum and Ian Ridgeway. — Ray Ewing

“They can come aboard and relive memories for anyone who sailed on her,” Ms. Van Ranst said.

Ms. Van Ranst hopes the weekend provides an opportunity for people to gather one more time around the Shenandoah.

“I’m just really hoping people show up and take this opportunity to come together as a community,” she said. “Everyone is so familiar with Shenandoah. She’s been an icon of the harbor for so many years and has meant so much.”

The Ocean Academy remains excited about the construction of a new boat, the Shenandoah II. The current goal is to raise another $1.3 million to complete the first phase funding goal of $6.25 million.

“We have raised just under $5 million toward our $6.25 million goal, which will enable us to sign a contract to begin construction on the hull,” Ms. Van Ranst said.

Once that first phase is complete, the Ocean Academy plans to raise an additional $3.6 million to fund Shenandoah II’s rigging, fitting out of the ship’s interior and establishment of an endowment for scholarships and expansion of the Ocean Academy’s programming. The final budget for all three phases will amount to approximately $9.8 million.

Capt. Robert Douglas at the helm. — Mark Alan Lovewell

The Ocean Academy team hopes Shenandoah II will help expand the program by serving students year round, as use of Shenandoah has historically been limited to the summer months because of her age and condition.

“We’ll be building a boat that’s easier to access. It will have engines, which will make it much more maneuverable,” Ms. Van Ranst said. “It will be much easier to sail in difficult conditions, and it will also give us the opportunity of running year-round programming, which is huge.”

But between the current ship and its next iteration, there are some unknowns, including the timeline for the next two phases of building the ship, and finding alternative vessels to continue the summer programming in the interim.

“They’ve been talking to a lot of different ship owners to see if there’s a suitable vessel out there that they can lease. As of right now, that boat has not materialized,” Ms. Van Ranst said.

If the group is unable to find a situation that works, the program will go on hiatus for a season or two.

“Of course they’d rather be able to continue programming.” Ms. Van Ranst said. “But if not, we’ll use that time to really look at long-term strategic planning, focus on the fundraising and how to get the community really involved in finishing Shenandoah II.”

For now, the focus is on saying goodbye to the ship that has been a part of the Island’s life for more than six decades.

“Inviting the whole community to a potluck and not knowing what’s going to happen is a little nerve-wracking,” Ms. Van Ranst said. “But I know people love Shenandoah, and I hope that they will show up for her because that’s really what this is about.”