The Wandering Walkabout Winnie Estelle

By Kate Livie

The lives of old Chesapeake boats are generally cyclical in nature. Their timbers were grown somewhere in the watershed, often on the Eastern Shore. They were built for and worked on the Bay’s waterways. Eventually, generally after one man’s lifetime, they were pulled up into a marsh and left to slowly sink back into the soil. Ashes to ashes, dust to dust.

But that’s not Winnie Estelle’s story. Over and over, since Noah T. Evans began working on a new deckboat more than a century ago, Winnie Estelle’s story has twisted and turned in unexpected and marvelous ways.

Over and over, Winnie has started another chapter—not an epilogue, but a whole new life. From the glory days of the Chesapeake’s oyster and crab industries, to hauling timber in the Caribbean, to cruising with snorkelers in Belize, to its celebrated return to the Bay’s waterways, Winnie’s epic backstory is anything but ordinary.

Winnie Estelle was built in 1920 by Evans, a Smith Island native who built and ran the mail boat, Island Belle, between Crisfield and the island. It’s not clear whether he used a boatyard on Smith or Crisfield to construct Winnie.

Despite the vessel’s murky origins, Winnie’s purpose was clear—to serve as a tractor-trailer for hauling and shipping in an era when roads and rail were insufficient to connect Chesapeake communities. Evans named his new “deckboat”—not a specific boat form but rather its function—after his two daughters and kept it for the next two seasons for his main hustle—running buyboats.

Like most buyboat captains, Evans was the critical connection between watermen harvesting fish and oysters and the city markets or big seafood packing houses. Winnie Estelle’s typical buyboat design—flat deck forward and a pilothouse/cabin aft, rigged with a mast and boom to load and unload cargo—was spacious and versatile.

Equipped with a gas engine that was 12 horsepower initially (and then upgraded to 35 by 1931), Winnie Estelle was slow but steady, perfectly built for carrying cargo on deck or in the hold.

As former owner Gene Marshall explained in an interview with buyboat historian Chris Judy, “She was strong. As long as you could stand up, she’d go ahead to it… Wind didn’t bother her.”

Over the next 40 years, the vessel passed through different hands—first, Warren Courtney of Virginia’s Northern Neck from the 1920s until the 1960s, and then, the Marshall family of Smith Island from the 1960s on through the mid-’70s.

Over the years, Winnie Estelle was pressed into all sorts of work—hauling fish, lumber, and fruits and vegetables, and buying oysters directly from the oyster harvesters and hauling them to market. Winnie also transported shells and seed oysters for private planters and the State of Maryland oyster program.

There are rumors of Winnie Estelle carrying a more titillating sort of cargo, especially during the Courtney years, which lined up with Prohibition. But the persistent whispers of Winnie Estelle being used for rum running appear to have originated in a case of mistaken identity.

Reports from Oct. 15, 1931, of a “$5,000,000 Rum Ring Smashed by US Here” describe a decoy trap set for two rum runners off the coast of Norfolk, Va., by the Coast Guard and name a vessel, Winnie Estelle, several times. But this boat was described as “speedy” and named as one of several “fast little ships” that supposedly evaded lawmen for over four miles in a cat-and-mouse chase on the water before it was apprehended by authorities.

According to CBMM Chief Historian Pete Lesher, these descriptors are the tell—this is not our Winnie Estelle. “Even with a new 35 hp engine, Winnie Estelle could have been overtaken by a boat under sail. Winnie’s never had much of a bigger engine than it has today. So, my guess? As unlikely as it seems, I think there were two Winnie Estelle’s. One a buyboat, one a rum runner, likely a speedboat.”

Buyboat Winnie Estelle might not have been a Prohibition-era rum runner, but there would definitely be plenty of rum in its future. Lesher provides a little backstory for the next walkabout chapter in the Winnie Estelle story. “After 50 years, maybe Winnie is getting a little tired, but if the boat was truly worn out by that time in the

1970s, it would have been run up a gut. But the fact that it was sold and taken down to the Gulf of Mexico shows that there was some life left.”

According to Lesher, it wasn’t uncommon for Chesapeake vessels in Winnie Estelle’s rough-but-stillserviceable shape to leave Smith, Deltaville, or other Chesapeake Bay buyboat communities and head south to the islands. “What’s different about Winnie is that it was almost always a one-way journey. They didn’t come back from the warmer water and all the happy creatures eating away at them. It could have been a death knell. But in this case, it wasn’t.”

Winnie Estelle was sold out of the Chesapeake Bay by the 1970s. Along the way, the vessel changed hands several times, was restored in 1982 by new owner Jerry McDermott, and then pressed into service transporting pine lumber from Honduras to Belize.

After just one run, Belize closed lumber importation to protect its local timber industry, so McDermott had to try another tack. It was time for those spacious decks to haul a new sort of cargo: tourists.

And so, Winnie Estelle began a new chapter as a day cruiser. Carrying tourists for snorkeling, dive charters, and sightseeing, Winnie was operated from Belizean vacation destinations like Ambergris and Caulker Cayes.

Over time, booze cruises in warm waters and the relentless onslaught of sea worms took their toll. In need of an enormous amount of work, Winnie Estelle was scuttled in 1985, left to the corals and waves.

For any other boat, this would have been the end, but thanks to a man with a vision and boatbuilding skills, Capt. Roberto Smith, Winnie Estelle once again survived.

Before deciding to undertake such a huge project, Smith traveled to the Chesapeake to learn more about buyboats. “Some of the old hands in the boatyards convinced me that was the thing to do,” Smith said in an interview. The visit inspired him, and in 1986, he began a five-year restoration of the vessel.

Belize, famous for its exportation of timber, was an excellent source of the native heart pine, cabbage bark, and other durable, rotresistant woods that Smith used in the painstaking restoration process.

Later owner Michael Whitehill praised the materials Smith had sourced. “The cabbage bark was hard as a rock. And the Honduran pine on decks was like a brick bat. It was careful work, all done by hand tools, adze.” Smith worked board by board, careful not to change the vessel fundamentally and to stay faithful to the buyboat’s traditional form. He installed a Caterpillar motor, hired local artisans to rebuild the decks and cabin, and in 1990, Winnie Estelle headed to San Pedro for its next chapter.

The newly restored Winnie Estelle began a second run as a tourist charter vessel, this time under the operation of Capt. Smith. Images and promotional brochures from this period show Winnie equipped with a big sun shade, low-slung deck chairs, and hammocks. A sunset cruise onboard came with local rum drinks included.

For more than a decade, Smith invited lucky passengers to make memories in the blue Belizean waters. Every year, at the end of the season, he was careful to take Winnie Estelle to freshwater to eliminate the sea worms in the hull.

Winnie was still in great shape, but it was Smith who was starting to think of retirement. By 2012, Smith had moved Winnie Estelle to Fronteras, Guatemala, close to freshwater Lago Izabal. There, the worms couldn’t harm the hull while the buyboat awaited its future.

Back near the Chesapeake Bay, Whitehill, an engineer by trade, found himself out of work due to the recession and open to new ideas. He started kicking around the notion of starting a small business running a boat for weddings and other outings.

Buyboats seemed ideal— beamy, comfortable, and classically Chesapeake. “I wanted something with some size to it. I looked at Mobjack, Crow Brothers, Ellen Marie. I even checked out a few lobster boats in Maine. But everything was too run down and would require too much time and money. That’s when I got a lead from another buyboat owner.”

Word had spread about Smith’s retirement and the extensive rebuild Winnie Estelle had undergone at his hands. Whitehill called a broker in Rio Dulce, Guatemala, to get the scoop. “I was just fascinated by the story. My imagination took over, overcoming sense.”

Whitehill ended up flying down to Guatemala to see Winnie Estelle and was impressed by Smith and the vessel itself. “Winnie was in just excellent shape. Roberto just popped in Dutchmen wherever he found rot, but the lines were true. He was so careful with that boat. Only loving fingertips for Winnie.”

Whitehill would fly down twice more to seal the deal, once to haul the buyboat at a yard he refers to as “tetanus alley” at the mouth of Lago Izabal, and the next time to prep for the Gulf crossing that would bring Winnie Estelle back to the Chesapeake.

On that last trip, Whitehill gave Smith a check for the buyboat, but with a caveat. “Roberto was key to all of it—if there was full genius in any of it, it was paying the full purchase price on the condition that he sail with me to Key West.”

By May 5, 2012, Whitehill and Smith set sail—sometimes literally— across the Gulf from Guatemala to Key West, stopping in Belize, Mexico, and then heading into open water. “We had a hell of a nice cruise from Isla Mujeres to Key West. At one point, we were swatting away flying fish. We had a Garmin the size of a pocket knife, full charts, and a compass that I had never really checked in advance. For the trip, we had a multicolored drifter that stabilized the boat nicely and a Genoa and jib on the Gulf. I actually clocked her at 12.2 knots under sail and engine power. I’m pretty sure that’s the fastest she’s ever gone.”

Once in Key West, delivery captain Jim Johnson took over from Smith and continued with Whitehill up the Intracoastal Waterway. News had reached some of the buyboat communities of Winnie Estelle’s return to the Chesapeake, and by the time Whitehill and Johnson reached Deltaville, Va., the energy was electric. “There’s a huge deckboat community, and the reception in Deltaville was unreal—like a homecoming. The marina was just swamped with people taking pictures. Folks took us in, bought us a meal. All out of this maritime reverence for old souls.”

Upon reaching the Chester River, Whitehill got two slips at Piney Marina Yacht Haven and started undertaking the massive work to make Winnie Estelle USCG compliant. “I stripped her down, down to bare wood. It was like a new relationship, getting to know somebody. You find the scars, the bumps. You could read her history and repairs over time.”

Whitehill went on to check off all the necessary elements the Coast Guard requires to carry passengers— fire suppression, side rails, life jacket boxes, and so much more.

While Whitehill toiled in Langford Bay, word of the USCG upgrades was spreading. Whitehill laughs. “I got all ready to go and the museum bought her out from under me,” he said.

The Chesapeake Bay Maritime Museum was looking to find a replacement for its longtime passenger vessel, Mr. Jim. Thanks to Whitehill’s efforts, Winnie Estelle checked all the boxes.

Former CBMM President Langley Shook, Lesher, and other CBMM staff visited the vessel and saw the possibilities—not just for interpretation, but for interactivity.

Winnie Estelle represented both a classic Chesapeake vessel type and a comfortable way for CBMM guests to have on-the-water experiences.

Ultimately, Whitehill sold his new/ old buyboat to CBMM, and the rest is history.

“CBMM has used its waterfront from its founding as part of its exhibits,” said Lesher. “And we have outstanding examples of Chesapeake Bay types: the winningest skipjack, the classic dovetail. But Winnie Estelle’s strength is that it is not an exceptional vessel, it is a typical vessel.

“It tells an everyday working story about the watermen and the Chesapeake of the first half of the 20th century and fills an important element in our maritime narrative about the way seafood got to market.”

Today, after 103 years of exciting adventures, Winnie Estelle is back on the hard, getting the necessary work such a venerable vessel needs for revitalization. Now one of only 30 or so buyboats, it has become a touchstone of the Chesapeake’s past.

A survivor from the Chesapeake’s golden age, Winnie Estelle has persisted because of many loving restorations and owners over the last century, CBMM included. From the Bay to Belize and back again, Winnie Estelle will once again go back to the work it was built and rebuilt for—hauling cargo (passengers now) and cruising strong and steady on Chesapeake waters. ★