The Chesapeake cowboys rode into St. Michaels, Maryland on a blistering August Sunday. The air was filled with the aroma of crab seasoning and diesel exhaust, mixed with the scent of light beer and lime. A couple thousand spectators gathered in the Colonial-era tourist town on the Eastern Shore, 80 miles from Washington, D.C. to witness the unique competition that is boat docking in the Chesapeake Bay. Fans squeezed into the hot bleachers overlooking the Miles River, while others balanced precariously on dock pilings without spilling their drinks. The atmosphere was electric, with a DJ playing and the crowd eagerly awaiting the start of the event.
The annual boat-docking competition, held at the Chesapeake Bay Maritime Museum, is part of a circuit that travels to various towns in rural shoreline areas in Maryland and Virginia during August and September. The competition was first held in 1971, born out of the watermen’s desire to turn everything into a competition. Today, winners can earn thousands of dollars or even just some fuel money to get home. Despite the competitive nature of the event, there is still a sense of camaraderie among the participants.
The competition begins with each pilot racing against the clock to dock their boat. They have to navigate tight spaces, reverse at high speeds, and then come to a stop just inches from the bulkhead before scrambling to secure their lines. The competitor who completes the task in the shortest time wins. The crowd eagerly cheers on the participants, enjoying any mishaps along the way.
The cowboys, as the competitors are fondly known, had been competing in various towns along the Chesapeake Bay before arriving in St. Michaels. The competitions attract a diverse crowd, from locals dressed in sailboat attire to those wearing camouflaged Crocs or rubber fishing boots. The events have gained popularity on social media, with some posts receiving millions of views. The Chesapeake Bay even has its own social media star, Luke McFadden, who showcases the life of a waterman to his 1.6 million TikTok followers.
While the docking competitions provide entertainment and celebration of the watermen heritage, there is a bittersweet undertone. The number of licensed watermen has been declining over the years due to stricter regulations, an aging workforce, and the need for more migrant workers in the seafood industry. Many watermen have had to find alternative sources of income, selling their boats or transitioning into tourism or transportation services.
As the sun sets on the boat-docking competition in St. Michaels, a sense of nostalgia lingers. The watermen’s way of life, closely tied to nature and the bay, may be fading away. But for now, the Chesapeake cowboys continue to ride on, showing off their skills and keeping the spirit of the watermen alive.
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