Editor’s Note: RVA Magazine is partnering with the Virginia Museum of History & Culture on coverage related to America’s 250th anniversary, including Richmond SailFest and the upcoming IllumiNation. Also, filmmaker Justin Black of Headwaters Down is sailing aboard the Pride of Baltimore II as it makes its way from Norfolk to Richmond. Follow along with his real-time coverage of the journey HERE.
At some point Thursday afternoon, if the wind cooperates, a black-hulled schooner with towering cream-colored sails will round the bend of the James River and glide toward Richmond, looking as though it has slipped out of another century.
Its masts rise nearly 100 feet above the water with cream-colored sails stretching out overhead. Rigging crisscrossing the sky in a web of rope and timber that looks almost impossible against the backdrop of a modern city. For a brief moment, Richmond will look less like a 21st century capital and more like a river port from back when the city was founded.
The vessel is the Pride of Baltimore II, one of several tall ships making the journey to Richmond for SailFest, part of the nationwide commemoration of America’s 250th anniversary. Alongside the schooner Virginia and the Dutch vessel Oosterschelde, the ships will travel up the James River and dock along Richmond’s waterfront, offering visitors a chance to step aboard vessels that connect directly to centuries of maritime history.
Most Richmonders have never seen ships like these on the James. The sight of towering sails moving upriver feels almost out of place, as though history has briefly escaped the pages of a book and returned to the water.
And depending on who is watching, those ships may carry very different meanings.
Photos of Pride of Baltimore II by @naval_aircrew
For some, they evoke exploration, trade, and the mythology surrounding America’s founding. For others, they bring to mind colonization, slavery, military conflict, and the movement of people across oceans both willingly and by force.
For Richmond specifically, they are a reminder that the city itself exists because ships could once travel this far inland.
“That’s why the city’s here,” said historian Gregg Kimball of the Shockoe Institute.
Kimball describes Richmond as a classic fall line city, the westernmost navigable point on the James River where goods from the interior could be loaded onto ocean-going vessels. Long before highways and railroads connected Virginia to the rest of the country, the river was the city’s lifeline.
Richmond’s waterfront once bustled with activity. Grain from western Virginia moved through the city. Coal and iron products were exported to markets around the world. Canals, locks, warehouses, mills, and shipyards transformed the riverfront into one of the South’s busiest commercial corridors. Sailors, merchants, laborers, immigrants, and enslaved people all moved through the same waterfront landscape.
“It would have been,” Kimball said, “lots of black workers, some enslaved, some free, lots of seafaring people from all over the world really working down there on the docks.”
That history contains triumphs and contradictions alike.
The same river that carried commerce and opportunity also connected Richmond to the domestic slave trade. The same waterways that brought settlers and goods to Virginia also marked the beginning of profound upheaval for Indigenous communities. The story of ships on the James is inseparable from the larger story of America itself.
That complexity is something organizers say they are embracing rather than avoiding.
“We don’t want to tell one story, one narrative,” said Sam Florer, Director of Public Programs at the Virginia Museum of History & Culture.
While SailFest includes fireworks, live music, ship tours, and family activities, Florer says the goal is also to encourage visitors to think more deeply about the history surrounding them. Educational partners, historical interpreters, exhibits, and Indigenous perspectives will be incorporated throughout the festival.
“We hope that people come to see the boats, to see the fireworks,” Florer said, “but then we’re going to provoke them to think a little deeper.”
For Captain Michael Fiorentino, who will bring the schooner Pride of Baltimore II upriver from Norfolk, the ships represent something else as well: continuity. A former theater professional who found his way into maritime life through volunteer work at New York’s South Street Seaport Museum, Fiorentino has spent decades helping preserve and operate historic sailing vessels. While modern safety equipment, engines, and navigation systems exist below deck, much of the fundamental experience remains unchanged.
“Sailing is slow to change,” he said. “The wind still fills canvas, the ropes still guide the sails and the river still carries the vessel forward.”
For a few days this summer, Richmonders will have the opportunity to stand along the James and watch these ships arrive much as generations before them once did. The emotions they evoke will not be the same for everyone. But perhaps that is the point of commemorating 250 years of American history honestly. Not finding a single story everyone agrees upon, but recognizing that the same river has carried many stories, and that all of them helped shape the city waiting on the shore.
Main photo of the ship Virginia, courtesy of Virginia Museum of History & Culture
Richmond SailFest takes place June Friday 12-14 at Great Ship Lock Park and along Richmond’s historic riverfront. Admission is free.
Friday, June 12
10:30 a.m. – 11:00 a.m. Opening Ceremony
11:00 a.m. – 6:00 p.m. Public Ship Tours
12:00 p.m. – 1:00 p.m. Rappahannock Whalers (Sea Shanties)
1:00 p.m. – 2:30 p.m. Plunky & Oneness
2:30 p.m. – 3:30 p.m. Woody Woodworth & The Piners
3:30 p.m. – 5:00 p.m. Plunky & Oneness
5:00 p.m. – 6:00 p.m. Heart of Ireland
Saturday, June 13
10:00 a.m. – 6:00 p.m. Public Ship Tours
11:00 a.m. – 12:30 p.m. Garden Variety String Band
12:00 p.m. – 4:00 p.m. Paddle In Your Park with RVA Paddlesports
12:30 p.m. – 1:30 p.m. Nathan Elliott (Native American Flute)
1:30 p.m. – 3:00 p.m. Bio Ritmo
3:00 p.m. – 4:00 p.m. Swingers Jump Rope Team
4:00 p.m. – 5:30 p.m. Justin Golden & The Devil’s Coattails
5:30 p.m. – 6:30 p.m. Ezibu Muntu
6:30 p.m. – 7:30 p.m. Richmond Symphony
9:00 p.m. – 9:30 p.m. Fireworks, Drone & Music Spectacular Over the James River
Sunday, June 14
10:00 a.m. – 4:00 p.m. Public Ship Tours
11:00 a.m. – 12:00 p.m. River City Taiko
12:00 p.m. – 2:00 p.m. No BS! Brass
12:00 p.m. – 4:00 p.m. Paddle In Your Park with RVA Paddlesports
2:00 p.m. – 2:30 p.m. Mile of Music Finale Performance (Richmond Symphony)
2:30 p.m. – 4:00 p.m. U.S. Fleet Forces Band
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