May 20, 2024
Annapolis, US 62 F

1920 buyboat Winnie Estelle joins floating fleet at CBMM

Winnie Estelle
On April 1, the historic 1920 Chesapeake Bay buyboat Winnie Estelle arrived in St. Michaels, MD at the Chesapeake Bay Maritime Museum (CBMM), where she will remain as the new workhorse of CBMM’s floating fleet for scenic Miles River cruises and a wide variety of on-the-water educational programs. Winnie was used around Smith Island as a workboat for more than forty years, carrying seafood and produce to market across the Chesapeake Bay. Drop-in Miles River cruises for up to 45 passengers begin this May, with same-day tickets available at the museum’s welcome center and store. For more information, visit

On April 1, 2014, the historic 1920 Chesapeake Bay buyboat Winnie Estelle arrived at the Chesapeake Bay Maritime Museum (CBMM) in St. Michaels, MD, where she will remain as the new workhorse of CBMM’s floating fleet for scenic Miles River cruises and a wide variety of on-the-water educational programs.

The Winnie Estelle joins CBMM’s floating fleet of historic boats, which includes the recently restored 1955 skipjack Rosie Parks; the 1889 nine-log bugeye, the Edna E. Lockwood; the 1912 river tug Delaware; the 1909 seven-log crab dredger Old Point, the 1934 dovetail Martha; the 1931 Potomac River dory boat; and the 1961 tuck-stern, Jackson-built Pot Pie skiff. The authentic buyboat replaces the museum’s replica buyboat Mister Jim, which has operated as a passenger boat since 1982. The museum currently has the Mister Jim for sale.

“About a month ago, we began fundraising to acquire the Winnie Estelle,” said CBMM President Langley Shook. “We are so fortunate that a generous donor, who wishes to remain anonymous, stepped right up to purchase her for an undisclosed amount to donate her to the Museum.” CBMM will engage in fundraising to build an endowment to cover ongoing and long-term maintenance of the historic buyboat.

Over the next few weeks, the Winnie Estelle is expected to receive her U.S. Coast Guard designation as a charter vessel to carry up to 45 passengers. A volunteer corps of USCG-certified captains and their volunteer crew will operate the vessel, with the museum’s boatyard handling Winnie’s upkeep and maintenance.

The Winnie Estelle will be used by CBMM for drop-in public cruises, student ecology tours, a floating classroom, private charters, weddings, and more. Beginning in May, scenic Miles River cruises on the Winnie Estelle will be offered Fridays through Mondays. Four, thirty-minute cruises will be offered daily at $15 for non-members, $10 for CBMM members and $5 for children under six. Same-day tickets will be issued at the museum’s store or welcome center.

“Imagine a special birthday party, a sail for your kids or grandchildren, or a sunset cocktail cruise before a wedding rehearsal dinner,” commented Shook. “This is a great opportunity to get out on the water for an authentic Chesapeake experience.”

The Winnie Estelle was built in Crisfield, MD, by Noah T. Evans in 1920. She’s nearly 65′ in length overall, with a 17-foot beam and a 3-1/2-foot draft, making her easily maneuverable in shallow water destinations. She displaces 42 tons of water and is powered by a Caterpillar diesel.

Winnie was used as a workboat on the lower Chesapeake for more than 50 years, carrying seafood and produce to market across the Chesapeake Bay. In the 1970s, she made Belize her port of call, where she operated as an island trader, carrying lumber from Honduras to Belize, and later as a charter boat for divers. In early 2012, Michael Whitehill of Centreville, MD, purchased the boat, returning her to the Chesapeake Bay on June 17, 2012 with a first stop in Deltaville, VA, where she was greeted by a cheering crowd of onlookers.

A Chesapeake Bay buyboat was historically used for buying and selling seafood. Buyboats purchased oysters or fish from watermen in remote parts of the Chesapeake and carried the fresh catch to city markets or seafood packing houses. According to Larry Chowning, author of the book Chesapeake Bay Buyboats, beginning in the early 20th century, motor buyboats were generally about 40 to 100 feet in length, with a mast and boom forward of the hold, a pilot house aft, and the hull decked over. Depending on their function, similar boats were called freight boats, run boats or crab dredgers, and also called deck boats or mast boats. With her bottom built in deadrise fashion like most other wooden workboats used by the watermen and historically used for buying crabs and fish, the Winnie Estelle is a typical example of the type—though she is rare for surviving in such an unaltered fashion.

“The Winnie Estelle is the finest restoration of a Chesapeake Bay buyboat that I have ever seen,” commented Naval architect Melbourne Smith when he visited Belize and sailed aboard the Winnie Estelle. Melbourne Smith was the overseer of the construction of the sailing vessels Californian and Pride of Baltimore II. Melbourne came to Belize seeking the same Belize lumber utilized on the Winnie Estelle for these ships.

The Chesapeake Bay Maritime Museum in St. Michaels, Maryland is dedicated to preserving and exploring the history, environment, and people of the Chesapeake Bay. With 18 waterfront acres in the historic town of St. Michaels, the Museum offers changing exhibits, demonstrations, boat rides on the Miles River, and annual festivals that celebrate Chesapeake Bay culture, boats, seafood, and history. Learn more by visiting CBMM in St. Michaels or at

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