The schooner Shenandoah left Tarpaulin Cove on Friday with an escort of sail and motor boats, along with her last group of students from the Chilmark School on board. At the end of the season, her current operators, the Martha’s Vineyard Ocean Academy will retire her. Captains Ian Ridgeway and Casey Blum are determined to build a steel boat with engines.

An easy sail from Vineyard Haven, Tarpaulin Cove makes an extremely rare harbor among southern New England’s crowded waterfronts, where a schooner without engines has the space to round up with a crew of children, drop her anchor and spend the night under oil lamps in a setting from the late-19th century. This has been the privilege of Island school children for over 50 years.

On Friday morning in my own boat, I didn’t keep up with Shenandoah’s long stride as she made her way across the Sound. It isn’t often I get becalmed between tides. Instead of starting my engine I let the parade disappear in front of me and jigged a lure off the bottom.

Back in Vineyard Haven that afternoon, the two schooners that have been in the harbor almost as long as Shenandoah, Malabar II and Ishmael, did circles under full sail to welcome her home. Both boats included people who lived, worked, sailed and learned on Shenandoah. Both boats are run by people who did not bring them into the harbor of the Island’s past. These are younger people who have made these old boats a part of their lives, and work really hard to maintain and sail them. I motored to a mooring in a big hurry. I had caught a sea bass and it looked like it was getting hot in the bucket.

Saturday in Vineyard Haven saw Shenandoah on the dock at Coastwise Packet Company for a send-off celebration. On the same day, the boatyard at Gannon and Benjamin next door hosted the annual Pat West Gaff Rig and Schooner race. Pat West was an Island character particularly invested in old Island ways. Later in life, as the Island changed and the hippies showed up, he befriended them, becoming one of many conduits between many Island cultures. His boat Venture became Nat and Pam Benjamin’s family yacht. Stories about Pat are still currency around the waterfront.

During the race, I sailed on the ketch Ayuthia with her owner and captain Lyle Zell and a crew of friends. Ayuthia is another boat that has managed to move between generations and keep her place in Vineyard Haven. It has taken most of Lyle and his wife Abbie’s free time over the past five years to get the almost 100-year-old boat into a condition where it looks and works like a fine yacht, but it’s still not a race boat. The crew lazed in the sun on the dry deck, at the back of the fleet, where we were able to admire the fine craftsmanship that went into the new decks up close.

At the awards ceremony, Lyle’s little sister, Capt. Greta Gannon, collected the prize for fastest schooner which went to her charge Rebecca, which was built by Gannon and Benjamin, in town behind Tisbury Marketplace. Nevin Sayre and Capt. Scotty DiBiaso won the gaff rig class aboard the sloop Lark, a boat that would have met its demise 10 years ago but was saved by John Kerry, our retired Secretary of State, who because of a childhood fascination with the boat, hired Gannon and Benjamin to rebuild it.

“There are cheaper boats. There are easier boats to sail, but you are all here and we appreciate it,” Scotty told the crowd.

“You’re not supposed to tell them that,” Nat Benjamin scolded the master of ceremonies loudly and joyously.

Because Shenandoah was on the dock next door there was a rare opportunity to climb around her with people who may have never seen the boat up close. Ben Muchin, a young boatbuilder who has worked at Gannon and Benjamin the past couple of years, marveled at the spaces down below.

“This is amazing,” he said. “I thought it was all rotten.”

He shook the gimbaled tables, he opened all the doors and shook his head in wonder.

At the race party afterwards, underneath Gary and Kristi Maynard’s over 100-year-old ketch, Violet, where she was perched on the railway, for maintenance and repairs, above the band, the crowd danced to the last minute of our sound ordinance’s demands.

Harry Ricciardi lives in Aquinnah.