From the fishing docks in Menemsha that have been her home for decades, an iconic, intergenerational fishing vessel set sail across the chop of Vineyard Sound on its way to Vineyard Haven Harbor last Thursday morning.
With a warm May sun gleaming down on her deck, this was a meaningful journey for the Little Lady, built in 1929, with her green and red wood hull and single mast.
She is now slated to begin a yearslong repair, with an estimated price tag of up to $2 million at the world-renowned shipyard of wooden boatbuilders Gannon and Benjamin Marine Railway on Beach Road in Vineyard Haven.
Little Lady is the sole remaining one-man, wooden dragger in New England, and represents a period when fishing traditions were passed down through generations rather than ruled by corporate gains and mass production.
Thursday morning’s sail from up-Island to Tisbury was a bittersweet moment for the vessel’s owner Dennis (“Denny”) Jason Jr. and his brother Bruce Gray, both of whom were on board during her fateful voyage — Little Lady will never again be the same as she was today.
The boat will continue to be a fishing vessel post-restoration, but on an educational basis, mainly through outreach to Martha’s Vineyard Regional High School students, with Jason standing at her helm through it all.
Jason, who took over as the owner of the vessel from his father in 2006, has been aboard Little Lady since his childhood. For him, Thursday’s sail was an emotional journey, rooted in three generations of stewardship. Jason’s grandfather, Leonard Jason Sr., was the first owner of the boat.
“There’s a lot of generational pride in the boat for sure,” said Gray. He said he and his brother have a lot of family memories associated with the vessel. “Denny has been an incredible captain and steward,” he said. “He takes a lot of pride in the fact that he’s carried the tradition on from his father.”
But in recent years, upkeep of the vessel had become a challenge, and an unmanageable expense.
“It’s a blessing and a curse,” Jason said about owning such a maintenance-intensive boat. He said repairs are expensive and take a lot of time, which has made it difficult to focus on fishing and simply getting her out on the water.
The total project cost of $2 million, estimated by the Fishermen’s Preservation Trust, has not been raised thus far, but fundraising is in the works. Voters in Chilmark on Monday passed a warrant article for the town to provide $100,000 as a kickstarter to the project. Now Little Lady will be in the hands of a half-dozen Gannon and Benjamin restorers, and repairs will take place once funded.
Nathaniel (“Nat”) Benjamin, co-founder of Gannon and Benjamin (G&B), who will be spearheading the restoration, intercepted the fishing boat on Thursday as it sailed from up-Island, watching Little Lady glide across the white-tipped ocean waves.
Benjamin took his motorboat, Patrol 2, from the G&B dock in Vineyard Haven to watch as Little Lady came around the sound and into the harbor. Her significance, he said, is not just in her beauty and artisan look, but also her utility. She’s among other 20th century boats of her kind that, according to Benjamin, are a “rare combination of science and art.”
“Little Lady can haul a drag with an air of nobility and purpose,” he wrote in an email to The Times. “Her proud sheer, strong bow, slight tumblehome transom, and sea-kindly hull set her apart. Little Lady evokes dignity and elegance, grace without glitter.
“Little Lady has soul.”
Benjamin said he’s eager to be a part of her repair, recalling his first time aboard the vessel about a decade ago as an experience of history and authenticity.
“You can feel the generations of fishermen who have been aboard,” Benjamin said. “There’s an Island history, there’s a personal history, and it’s a beautiful design.”
When Little Lady is in the hands of Gannon and Benjamin, they’ll be repairing planks, restoring the deck and frame, and replacing the rigging and wheelhouse. The vessel has needed pumpouts and watchful maintenance to stay afloat thus far, and is due for multiple upgrades.
Fundraising for the restoration has and will be a journey, too. The cost is substantial, but those close to the project say the payoff will speak for itself. Little Lady has been a symbol of community resilience, and the maritime root of Island life, for nearly 100 years, as well as being the last vessel of her kind on the East Coast. Those involved in the restoration said her repair is not just about her use, but also her impact and educational potential.
The Fishermen’s Preservation Trust published an informational guide on the Chilmark town page about Little Lady and ways to donate to the project. John Keene, president of the nonprofit, said the Fishermen’s Preservation Trust was founded to support the longevity of the Island’s working waterfronts. Providing information about these vessels and their continuance is part of that mission.
“[We want to] keep that fabric of Menemsha alive,” Keene said, and clarified that every town is a part of that working model for historic preservation.
Liz Packer — whose father, Ralph Packer, owns Tisbury Wharf Co., the dock that Little Lady was tied to before being lifted from the water and put in a shed at the Gannon and Benjamin boatyard to await repair — said the vessel is a part of the Island community.
“She’s very special,” Packer said. “And it’s gonna take a community to keep her going.”
The Little Lady’s past was marked with fishing trips, Menemsha memories, and sails across the open sea. Her future is intended to be one of education, maritime pride, and generational Island stewardship. Any fish caught on her going forward will be donated to the public schools and Island Grown Initiative’s Food Pantry, feeding the community still, but in a different way.
Since his ownership, Jason said he’s sanded and painted Little Lady almost every year to avoid any potential for rot. Her mast is chipped in some places, with the many layers of pale orange paint visible. The years of care for her are tangible, with past paint colors peeking through like the rings on a tree, telling her story. Jason is the third generation to steward this vessel.
“My grandfather would love to see this,” he said, looking out from Little Lady’s bow toward the ocean beyond her.
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Major key!
I never knew she was from 1929! I always wondered how many coats of paint she had. Nat Benjamin will restore her beautifully.
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