The Last Eastern-Rigged Side Trawler: An End of an Era

My image of what a proper fishing boat should be was formed in childhood by the eastern-rigged side trawlers that used to ply Watch Hill Passage on their way to and from the fishing grounds. Those vessels—deep-draft wooden workboats with sweeping sheer and an aft pilothouse—left an indelible impression on anyone who grew up along New England’s working waterfront.

Developed in the 1920s, eastern-rigged side trawlers were built for the hard, repetitive work of dragging nets. Their pilothouse sat toward the stern, with the working deck amidships where crews handled heavy gear and hauled nets over the side. A dory or two often rode above the pilothouse, ready for quick deployment. These design choices reflected decades of practical evolution in small-boat fishing technology and craftsmanship.

There were, of course, western-rigged draggers in the same waters—boats with pilothouse forward and working deck aft—but to many coastal observers the eastern-rigged style was the quintessential New England trawler. The names of these boats were part of their charm and heritage. As Gloucester fisherman Peter Prybot observed in his book White-Tipped Orange Masts, the vessels often bore evocative names honoring saints, places, seabirds, sea creatures, or the daughters and women of fishing families. Those names became part of the oral history of the fleet and of the communities that depended on them.

Change and technology, however, have a way of reshaping entire fleets. Just as the eastern-rigged side trawler once replaced the older dory schooner, a later wave of advances—steel hulls, higher-horsepower diesel engines and modern hydraulic systems—brought the stern trawler to prominence. Beginning roughly 45 years ago, those newer vessels began to supplant the wooden side trawlers, ushering in a modernization of commercial fishing that ultimately rendered many traditional designs obsolete.

The symbolic end of that eastern-rigged chapter arrived in early June when Gloucester’s last wooden side trawler was intentionally scuttled, sunk in 345 feet of water with the required federal approvals. The 67-year-old Little Sandra was given what her owners described as a graceful burial at sea. Capt. Bill Lee, a Rockport-based surveyor, consultant and former commercial fisherman, towed the dragger to her final resting place 18 miles off Rockport aboard his 44-foot vessel, Ocean Reporter.

“It’s definitely the end of an era,” Lee said. He noted that while there might be other relics somewhere along the coast, Little Sandra was the last active side trawler in Gloucester. The decision to sink her was made with careful consideration; the owners preferred not to have the boat crushed or simply discarded. Before the scuttling, all fuel, oil, filters, batteries and other potential contaminants were removed to comply with environmental and safety requirements.

Built in 1946 in Southwest Harbor, Maine, and originally named the Anthony & Josephine, Little Sandra was a heavy, purpose-built workboat. Constructed of longleaf yellow pine over oak frames, she weighed 56 tons and embodied the rugged, no-nonsense construction typical of midcentury wooden draggers. “She was a real sledgehammer boat,” Lee recalled. “Everything was rugged, big. Huge galvanized nails and bolts. There was nothing light-duty about her.”

When the sea chest was opened during the scuttling operation, Little Sandra took about 45 minutes to settle. Once her stern went under, the vessel disappeared in under a minute—“the boat just stood right up and went straight down,” Lee remembered. For those involved, the controlled sinking was a dignified way to retire a hard-working vessel and to acknowledge a chapter of maritime history coming to a close.

“A true schooner in miniature … but she was rough! On close inspection she looked as though she had been flung together by a band of our paleolithic ancestors — able shipbuilders perhaps, but equipped only with stone adzes.”

As working boats vanish, preservation efforts and museum displays become increasingly important for keeping maritime heritage alive. One notable survivor, the eastern-rigged wooden dragger Roann, is preserved at the Mystic Seaport Museum in Mystic, Connecticut, where visitors can study its lines and construction up close. For communities tied to fishing, these vessels are more than machines; they are carriers of tradition, family history and the craftsmanship of generations.

The sinking of Little Sandra is both an ending and a reminder. It marks the close of a distinct chapter in New England’s fishing history, while underscoring the practical and environmental choices communities must make when retiring large working boats. The memory of those eastern-rigged side trawlers—how they looked, how they were named, and how they served their crews—will endure in photographs, in museum exhibits, and in the stories told by the people who worked aboard them.