On Saturday evening, more than 200 people gathered on the Black Dog wharf in Vineyard Haven to celebrate the life and legacy of the Shenandoah. Earlier that day the legendary topsail schooner arrived from Tarpaulin Cove with a group of Chilmark students, completing its last sail after 63 years of service to the Island community.

Shenandoah arrived in the summer of 1964, captained by Capt. Robert Douglas, and has been a familiar site ever since in the harbor and the surrounding waters.

Guests gathered to share stories, listen to speeches from those who have worked on the ship over the years and shed more than a few tears.

Matthew Stackpole, the third first mate of the Shenandoah, spoke about his experience aboard the vessel.

“[Capt. Robert S. Douglas] used to say that one of his favorite boat names was Magic Carpet,” Mr. Stackpole said. “A magic carpet brings you to a different place, to a new world. And this vessel has been a magic carpet for generations of people. I think she’s done so much for the children on this Island, for them to have a sense of both their heritage, the history and the future.”

Capt. Ian Ridgeway spoke next, adding to Mr. Stackpole’s reflections with memories of his own first experience with Shenandoah.

“As Matthew said, it’s a portal into another world, a world where a lot of things make more sense than they do in the rest of the world today,” he said. “I first went on Shenandoah as a student....I was a high-energy kid that did not thrive in a classroom setting. I came out on Shenandoah and was immediately enamored by everything she offered to me. It was a place where my energy was valuable, where there was always something to do, always something to learn.”

That morning, those sentiments had been on display as 27 fourth and fifth-graders from the Chilmark School returned after a week aboard the Shenandoah. They had boarded the ship on Monday morning and spent six days sailing, learning the ropes and working together as a crew.

Their arrival back on land marked the close of Shenandoah’s final voyage, a historic milestone taking place as the kids were ferried back to shore to their waiting parents.

Kate Squire, principal of the Chilmark School, was among those welcoming the students back.

“It’s such a thrill,” she said. “It’s always so special. These kids, in particular, really understood the impact of this, being the last ones.”

The Chilmark School, along with the other Island elementary schools, has been involved with Shenandoah for decades, and Ms. Squire noted that the impacts of the relationship are tangible.

“We find kids come back more confident, connected and resilient,” she said.

Fourth-grader Pepper Eisner was a prime example of this, chatting enthusiastically with her family about the skills she learned and the experience she had.

“It was really fun to jump off the boat,” she said. “I was screaming in the air but then I landed in the water, and I was like, well, that was the shortest jump ever.”

Pepper said she learned how to raise the sails and what the nautical pins meant. Living on the boat was an adjustment at first, she admitted, but she soon appreciated her time on the water.

“The first night I slept terribly, but then I got used to it,” she said. “It made me want to go back on the water, but I’m also happy to be home.”

Ryan Bodnar, also a fourth grader, was the last student to step off the boat. When she reached the dock, she was crying. Her mom knelt down to comfort her, saying she was so happy Ryan was home.

“No, Mom!” Ryan said. “I’m sad because I didn’t want to leave!”

The emotional goodbye continued at the evening’s celebration. Musicians Rose Guerin and Buck Shank set the mood as attendees moved between the dock and tours of the ship.

“It’s bittersweet,” Capt. Casey Blum said. “The students this week were so joyful and they loved being aboard. It was really special to end [Shenandoah’s] career with Vineyard kids.”

The Shenandoah has long been a fixture of Island life and a rite of passage for children who have grown up on the Vineyard.

“This [voyage] served as a reminder of how important the experience is for generations of Islanders,” Mr. Ridgeway said. “It’s a part of who we are.”

Shenandoah’s legacy is deeply personal for Ms. Blum and Mr. Ridgeway, who brought their 18-month-old son on board for the day on Friday.

“It made me think about him sailing with his friends on Shenandoah II,” Ms. Blum said, smiling.

Mr. Ridgeway estimates that over 15,000 kids have spent a week aboard the Shenandoah, and 20,000 people in total.

“It has been a beautiful thing to watch all these youngsters come aboard,” he said. “This boat has done so much for all of us, and we don’t know what’s going to happen next. The future is unclear, but our promise, our goal, is that we’re going to keep this program alive. We’re going to build a new ship that can take thousands more students sailing, and offer a more sustainable program that’ll be able to operate year-round.”

Mr. Ridgeway said the organization has $900,000 left of its fundraising goal of $6.25 million to begin the first phase of construction on Shenandoah II. The total budget for the new ship is approximately $9.8 million.

A sunset toast to the iconic ship closed the evening’s festivities, before her four cannons were loaded and fired for the last time.

“Thank you so much for being here tonight,” Mr. Ridgeway said. “Thank you for loving Shenandoah with all of your heart, like I do. Thank you for supporting us and joining us on this journey into the future. Let’s celebrate this beautiful boat and all she’s done.”