Spy Maritime: The “Buyboats” are Coming to Chestertown and Oxford


The Chesapeake Bay Buyboat Association inaugurated its 2019 weeklong bay tour in Chestertown this weekend. Twelve buy boats from around the bay have joined the cruise that will continue on from Chestertown to the Kent Island Yacht Club Tuesday, the Oxford Yacht Club on Wednesday and will wrap up the tour in Cambridge starting on Friday.

“We have had a great weekend here in Chestertown,” 2019 organizer Dave Cantera. “Mayor Cerino, town council and staff have done a tremendous job with the marina project,” Cantera continued. “It is well suited to welcome larger historic wooden boats and we saw great numbers of visitors all weekend.” The CBBA thanked the Town for its hospitality with a community fish fry with live music on the Customs House lawn at the foot of High Street on Saturday evening.

The CBBA organizes the weeklong cruise in different parts of the bay annually to promote awareness of the buyboat’s history and role in the Bay economy for much of the 20th century before the coming of the two bay bridge spans.

“All of these boats plied the rivers and Chesapeake Bay delivering the bounty of the Chesapeake Bay and to Baltimore, returning with diverse backhauls that included barrels of household staples, ready to wear, tools, and empty cans from American Can Company bound for the Eastern Shore crab and produce processors,” Cantera explained. “The goal of this tour is to share this living history.”

Larry Chowning is the author of Chesapeake Bay Buy Boats, a history of the vessel published in 2003, has been following the annual buyboat tour on the Chesapeake since the first gathering of the CBBA in 2004 in Rock Hall. “These are fascinating vessels,” the author of 10 books commented.

Steve Bailey, captain of the Samuel M. Bailey, hails from St. Mary’s County. His vessel is the only known Bay buyboat to remain in the hands of the original owner’s family. “My grandfather had the boat built in 1957 and my family has had it on the water since,” Bailey shared. “I am proud to continue this Bay tradition.”

Kent County is the home of a number of buyboats, each one as unique as its owner. Cantera’s father Pat owned and raised his son around large wood boats on the Sassafras River. Cantera acquired his first buyboat in his early 20s. “Growing up, my dad taught me appreciation for the care of a wood boat,” Cantera mused. Cantera gives the greatest credit for the restoration of his flagship vessel, the Muriel Eileen, to Graham Ero of Still Pond, whose career is punctuated with many original and restoration showpieces.

The CBBA cruisers depart Chestertown on Tuesday morning.

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