Under a clear October sky last weekend, the Pride of Baltimore II, a 97-foot topsail schooner, glided through the calm waters of the Choptank, offering three groups of visitors a brief glimpse of its 19th-century heyday, when the river served as the epicenter of transit, economics, and politics.
This vessel, faithfully modeled after the Baltimore clippers of the War of 1812, marked one of three trips that day. The weekend featured six sails before concluding the ship’s 2025 Chesapeake season with a stop in Chestertown before returning to its winter port in Canton on the Inner Harbor.
The ship was under the capable command of Captain Jeff Crosby, one of the ship’s two rotating skippers. Growing up sailing on the Great Lakes, the Duluth, MN native joined the crew in 2008 and rose to captain in 2020.
It was a lovely weekend for sailing on the Choptank for the Pride of Baltimore II. The wind could have been a little stronger.
“Cambridge is great,” Crosby told The Spy. “There’s a lot of history over here, much of it tied to ships like the Pride. The intricate web of waterways on the Eastern Shore shaped their design, with fast, agile hulls built for winding rivers with shallow depths.”
As bos’un Kai Joswig, of Las Vegas, NV, and originally from Belize, barked orders repeated by the crew in unison, the ship slipped out of the Long Wharf and onto open waters.
The deck, lined with coiled ropes and wooden fixtures, buzzed with activity. The experience offered a hands-on connection to the ship’s traditions. The deck, lined with coiled ropes and wooden fixtures, buzzed with activity. The experience provided a hands-on connection to the ship’s traditions.
Pride II, with its tall masts and American flag, stands as a living testament to maritime heritage. Its lifeboat, aptly named the Chasseur (French for “hunter”), honors the 1812 clipper on which Pride II is modeled.
Captain Jeff Crosby learned to sail on the Great Lakes, and is a big fan of ice boating.
When it was time to man the halyards to raise the foresail and jib, guests, including Alex and Lisa Green, operators of Harriet Tubman Tours, added their muscle to the exercise. Alas, The Spy would have joined in but was fully occupied by his reportorial obligations.
The Greens’ presence was meaningful. Each of the weekend’s sails carried the theme ‘Sailing the Chesapeake Through Ebony Eyes,’ a tribute to Vincent O. Leggett – the ‘Admiral of the Chesapeake’ – whose work illuminated the Black maritime history on the Bay. Leggett passed away in November 2024 at age 71.
From Baltimore, Leggett founded the Blacks of the Chesapeake Foundation in 1984. His work chronicled the contributions of African American watermen, oystermen, and shipbuilders. His two books on the subject earned him the honorary title from former Governor Parris Glendening in 2003.
Alex Green grew up in Bellevue on the Tred Avon. His family worked on the water, and now he operates Harriet Tubman tours.
“When Vince was working on his book ‘Ebony Eyes,’ he interviewed all of the old black watermen, one of whom was my grandfather,” Alex Green said. “He wanted to hear all of his old stories. I met him then, and we became great friends.
“He mentored and encouraged me to share these stories when there wasn’t much public interest. We later became colleagues, and near the end of his life, I would step in to handle certain projects on his behalf.”
Longtime Dorchester residents, the Greens (Lisa’s family ties reach back to the Tubman era), have guided tours along the Harriet Tubman Underground Railroad Byway for over a decade.
Crew members take a break to chat with The Spy.
Launched in 1988, the Pride II replaced the original Pride of Baltimore, which was tragically lost in 1986 in the Caribbean to a microburst squall, claiming four lives. “It was just a freak of nature,” is how Crosby described the storm.
The new ship has since traveled 350,000 miles, visiting more than 200 ports across 40 countries. Since then, the Pride II has sailed more than 350,000 miles to over 200 ports in 40 countries, carrying Chesapeake’s maritime story from the Choptank to the world.
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