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Introducing the Thrilling World of Competitive Boat Docking


Sep 14, 2023

The Chesapeake Cowboys rode into St. Michael’s, Maryland on a hot and humid Sunday in August. As I stood in the tourist town on Maryland’s east coast, about 130 miles from Washington, D.C., I could smell the distinct scents of crab seasoning, diesel exhaust, light beer, and lime. A crowd had gathered to witness the unique competition known as boat docking, which only takes place on the Chesapeake Bay. Spectators filled the hot bleachers that overlooked the Miles River, while others stood elbow to elbow on the lighthouse deck. Some even balanced on the dock pilings without spilling their drinks. The atmosphere was filled with excitement as the DJ played love songs and the contestants prepared for the competition.

Ronnie, one of the competitors, compared boat docking to NASCAR but on the water. He shared this sentiment from his boat, the May Worm, also known as “Lacey Cup.” After a prayer for safety and the performance of “The Star-Spangled Banner,” the engines roared to life and the boats set off. Over the next two hours, the crowd cheered and winced as the boats, with names like Nauty Girl, Outlaw, and Hard to Handle, showcased their skill in backing up and maneuvering through tight spaces. Host Eric Emily, known as “Flea,” entertained the crowd with his East Coast eloquence and encouraged them to cheer louder for faster speeds.

The competition, held at the Chesapeake Bay Maritime Museum, is part of a tour that takes place in about 10 towns along the rural coasts of Maryland and Virginia in August and September. It began in 1971 and is believed to have originated from a Waterman’s desire to turn everything into a competition. Today, the winners can earn thousands of dollars in one day, which can help cover the costs of fuel and serve as a source of pride. Each pilot competes alone or with teammates for driving time, creating an exhilarating experience similar to extreme parking with a rodeo twist.

As the boats cleared their slips, they accelerated and swiftly changed directions, sometimes causing waves that soaked the fans. The boats then backed away and raced full tilt towards another narrow slide by the bleachers. It was an intense competition where precision and speed were key. The ideal outcome was for the boat to stop just inches from the bulkhead, and for the captain to quickly secure their lines to the pilings. However, accidents were not uncommon, and sometimes boats hit the pilings or failed to stop.

Jake Jacobs, the captain of Outlaw, one of the fastest boats in the bay, acknowledged the risks involved and emphasized the importance of not being afraid to scratch the boat. Jacobs, who won in two categories at St. Michael’s, could earn around $10,000 in a season. Some boats, including his, had sponsors from local landscaping and construction companies, who contributed to the competition in various ways.

The Chesapeake Cowboys continued their tour, competing in various towns along the Chesapeake Bay. Peyton Reese, the 9-year-old daughter of one of the competitors, was a fan favorite and often competed against adults. Her presence added to the excitement as she pumped her fist at her family in the stands. The atmosphere at each competition varied, with some events celebrating sailor heritage and others being more like lively parties.

While the boat docking competitions may not be broadcast on television, they have gained a following on social media platforms. The unique design of the Chesapeake Bay Deadrise, the state’s official national ship, has become a topic of interest among boating enthusiasts. Additionally, the decline in licensed sailors has been noted, with government regulations and an aging workforce contributing to the decrease. However, the passion for the Chesapeake Bay and its traditions remains strong among those who continue to navigate its waters.

As the competition drew to a close, the participants in St. Michael’s donated thousands of dollars to support athletes with testicular cancer. Similarly, the Taylor’s Island Boat Docking Challenge donated proceeds from tickets and refreshments to the local volunteer fire department. Each event had its unique atmosphere, with St. Michael’s exuding a quaint charm while Taylor’s Island showcased a more rustic ambiance.

The Chesapeake Bay boat docking competitions capture the essence of the region’s history and legacy. They are a celebration of the watermen’s way of life and a testament to the grit and determination required to navigate the Chesapeake Bay.

By Editor

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