A Buyboat Returns to the Bay

One of the surest ways to observe the inevitable transition of the Chesapeake’s working waterfront is to note the boats. Along the bulkheads and piers, humble harbors and Ego Alley, a motley assortment of vessels crowd the shoreline: sailboats, cabin cruisers, cigarette boats, runabouts, and hard-to-overlook yachts. What most of them share, beyond coolers full of cold beer, are their uses. These are boats for fun, boats to push a little wake in the water, with the captain and crew employing the classic ‘leisure wave’ in passing. Their varnish gleams, their burgees wave spiritedly, and the water lapping at their hulls create a scene both placid and timeless. Surely this is how it has always been, in these Chesapeake harbors? Full of recreational vessels at the ready to harness wind and power to explore the coves and creeks of the Bay’s endless shorelines.


     St. Michaels harbor from the Chesapeake Bay Maritime Museum’s waterfront today.

But as with so much of the Chesapeake’s most compelling vistas, all is not as it seems. Only in the last 75 years have many of the slips along the harbor been stacked with craft primed for diversion. Up until the 1950’s and 60’s, most of the waterfront communities were working towns, relying on the Chesapeake’s rich biodiversity to line their wallets and put food on the table. St. Michaels was no exception.


This wintertime shot of what is now the venerable Crab Claw restaurant along St Michaels harbor show the opposite of the modern port: the mounds of spent oyster shell, dilapidated picking houses, hogged skipjacks, and capable log canoes that made up the working waterfronts of the Chesapeake past. There were no fancy restaurants, no tasteful arrays of potted plants, no gleaming varnish or technicolor hulls. The boats that sidled up to the bulkhead were almost universally white, and by January or December would have been dingy with salt spray, crushed oyster dust, Bay mud, and rusting iron fittings. These were not vessels created for pleasure. Rather, they were serviceable workhorses, built from an odd number of logs, plying the Chesapeake as they hauled freight, dredged oyster rock, and generally plumbed the depths of the Bay for their finned livelihoods.


    Buyboats loaded with oysters at the dock. Image courtesy of the Mariner’s Museum.

Buyboats were a critical part of the Bay’s historical working waterfronts. These tireless jack-of-all-trades were used to buy fresh catch from watermen around the Bay and sell them at market (as suggested by their name), but that was just one of their roles. Buyboats also served as the Chesapeake’s 'work trucks,’ carrying watermelon or tomatoes on their broad decks in summertime from the verdant fields of the rural watershed to cities like Baltimore or Washington, taking passengers back and forth across the Bay, and hauling cargo that ranged from the US mail to (allegedly but possibly) bootleg liquor.


The Chesapeake Bay Maritime Museum has its own buyboat representing this proud tradition, Mister Jim, a replica which now hauls cargo of happy summer visitors and excited school age children rather than the ripe fruit and cold, succulent oysters of the Chesapeake’s halcyon days. Most buyboats that escaped a slow disintegration in the back coves of the Bay’s creeks and have survived to the modern era are like Jim- conforming to a new future as school vessels or tour boats. It’s not a guise that harnesses the brute strength of the buyboat’s build, but its a way to keep on working.

For one exceptional example however,  the Winnie Estelle, taking tourists out on daytrips was where she ceased being ordinary. Because the Winnie Estelle, a buyboat as native to the Bay as a chicken-wire crabpot, found herself in the last place you’d look for one of the Chesapeake’s icons: Belize.


                         The Winne Estelle cruising off the coast of Belize.

The Winnie Estelle was built in 1920 by a Crisfield shipwright, Noah T Evans, who named the boat after his two daughters.Originally designed to carry oysters to port during the tail end of the oyster boom, she was soon pressed into other services as the harvest waned and cobbled together a series of motley jobs typical of buyboats in the 20th century. The 1970’s found the Winnie Estelle transporting lumber as far south as the coast of Belize, but the warm climate and heavy use put her old bones to a hard test. Found adrift on a reef in 1986, a captain, Roberto Smith saw the life still in her, and through an infusion of Honduras heart pine and Belizean cabbage bark she rose reborn and rebuilt with strong Central American bones. But she wasn’t destined to live out her half-life as an ex-pat in the cerulean swells of Belize, running tours forever. The Bay was calling her home.


                  A video of the reincarnated Winnie Estelle in Belize, ca. 2008.

Today, the Winnie Estelle, one of the Chesapeake’s most adventuresome buyboats, is back in the Bay of her youth.

Purchased by a private Kent County resident, her last days in Belize were in early May of 2012 before she headed 1700 miles north to her native estuary. In 2012, she met up with the remaining remnants of her kind in Crisfield, for the 2012 Chesapeake Bay Annual Buyboat Reunion. The town welcomed their prodigal daughter back with open arms, and alongside other the other oyster haulers and watermelon carriers that stood white and proud beneath a blisteringly blue sky, she looked precisely the part of the 'tractor trailer’ of the Chesapeake past.

Today, she is slated to be the newest addition to the “floating fleet” of historic vessels at the Chesapeake Bay Maritime Museum, where she’ll continue to carry passengers, sharing the magic of the Bay’s maritime legacy with fresh purpose.

But look past the throngs of summer visitors, and underneath her glossy whiteskin, the Winnie Estelle stillhas a few secrets. With a belly full of Belizean hardwoods and planks that have been bathed in the mangrove salt tides, this is one buyboat that has a story to tell that is anything but traditional.


          The Winnie Estelle at the 2012 Chesapeake Buyboat Reunion. Photo source