The Chesapeake cowboys made their grand entrance into St. Michael’s, Md. on a hot Sunday in August. The scent of crab seasoning, diesel exhaust, light beer, and lime filled the air. A crowd of a couple thousand people had gathered in this Colonial-era tourist town on Maryland’s Eastern Shore to witness a one-of-a-kind competition unique to the Chesapeake Bay: boat docking.
Spectators filled the hot bleachers overlooking the Miles River, stood elbow to elbow on a lighthouse deck, and some even perched on dock pilings without spilling their drinks. A DJ played a love song to ice-cold, long-neck beers. The atmosphere was reminiscent of NASCAR, but on the water, according to one participant, Ronnie Reiss, also known as “Reissy Cup,” aboard his boat, the May Worm.
After a safety prayer and the playing of the “Star-Spangled Banner” by Chris Stapleton, a woman yelled into a microphone, “Start your engines!” The crab and oyster boats, known as “deadrises,” due to their ability to navigate the shallow Chesapeake Bay, roared to life.
For the next two hours, fans cheered and flinched as boats like the Nauti Girl, Outlaw, and Hard to Handle reversed out of their slips, engulfed in black smoke. The louder the crowd yelled, the faster the boats went, as the MC, Erik Emely, better known as “Flea,” explained with his distinctive Eastern Shore accent, which almost sounded Southern.
The annual boat-docking competition takes place at the Chesapeake Bay Maritime Museum and is part of a circuit that visits around 10 towns in rural shoreline areas of Maryland and Virginia during August and September. The first event was held in 1971, fueled by the watermen’s innate urge to turn everything into a competition, as a video from ChesapeakeStory.com suggests.
“It was all about watermen challenging each other, saying I can tie up faster than you. It was all about bragging rights. Back then, the only thing they won or bet on was a tray of soft crabs,” recalled Mr. Emely.
Today, the winners can earn thousands of dollars in a single day or enough money for fuel to get home. The competition still carries a sense of pride.
Each pilot competes, either alone or with teammates, against the clock. It’s like extreme parking with a touch of rodeo at the end. After maneuvering their boats out of their slips, competitors give it full throttle, making hard turns and creating a wake that sometimes splashes the fans (although the 90-degree heat didn’t seem to bother anyone in St. Michael’s that day). The boats then reverse with full speed, skillfully backing into another narrow slip by the bleachers. Ideally, the boats come to a stop mere inches from the bulkhead, and the captains must scramble to secure two lines to the pilings. The fastest competitor wins.
“I like to think that we’re more of a show, so no one really loses,” said John Ashton, captain of Miss Julie.
Occasionally, the boats collide with pilings, or they fail to stop in time. The crowd finds joy in any mishaps.
“We crash all the time,” admitted Jake Jacobs, captain of Outlaw, one of the bay’s faster boats. “If the thought of scratching your boat ever crosses your mind, you’ve already lost. You can’t be afraid to damage your boat.”
Mr. Jacobs, 37, triumphed in two categories in St. Michael’s, receiving trophies and celebrating with a Corona at the end of the day. He estimated that he could earn around $10,000 in a season. His boat, along with a few others, has sponsors, mainly local landscaping or construction companies.
“Some local businesses like to lend a hand, whether it’s a $500 contribution to put a small sticker on the boat or providing a tank of gas to get them to the competition,” shared Jason Murphy, whose company, Peake Contracting, had its name showcased on Mr. Reiss’s May Worm.
These “cowboys,” a name the participants gave themselves when attempting to land a reality show over a decade ago, had competed in Cape Charles, Va., the previous week. They still had a few more competitions remaining in Solomons Island and Tilghman Island. However, Peyton Reiss, Mr. Reiss’s 9-year-old daughter with turquoise braces, was the fan favorite up and down the bay. She usually competed in the kids’ categories, whenever available, but often found herself pitted against adults. She would pump her fists at families seated in the bleachers.
In his writings, author James A. Michener, who resided in St. Michael’s for several years, described Chesapeake watermen as “quiet heroes, echoes of that long-distant day when most Americans made a living close to nature.” Some of these competitions serve as celebrations of the watermen’s heritage.
Others, like the Extreme Boat Docking Competition in Salisbury, Md., held at a bar on the Wicomico River, are more of a party that lasts all weekend.
In rural Dorchester County, not far from St. Michael’s, the Slaughter Creek Marina hosted the Taylors Island Boat Docking Challenge on another scorching August Sunday. Fans flocked to the marina, parking their cars on the shoulders of a two-lane road surrounded by marshes and farmland. The St. Michael’s event’s attendees had donated thousands of dollars to assist a competitor suffering from testicular cancer, while the Taylors Island competition’s proceeds from ticket sales and refreshments, amounting to around $22,000 the previous year, went to the volunteer fire department of the small town.
In charming St. Michael’s, there were sailboats, pastel polos, and boat shoes. The atmosphere in Taylors Island, however, felt a bit more rustic, with attendees sporting Orioles caps, camouflage Crocs, or rubber fishing boots.
The organizers had ordered 150 cases of beer, although many attendees opted for an “Orange Crush,” a Maryland shore favorite made from orange vodka, triple sec, Sprite, and, as the locals in Taylors Island emphasized, freshly squeezed orange juice. A bartender at the crush tent, originally from New York and unfamiliar with the drink before moving to the Eastern Shore in 2005, mentioned that he had served hundreds of Orange Crushes before noon.
Many people compared the boat-docking competition and its atmosphere to NASCAR, while others noted similarities to tractor pulls and rodeos, all competitions rooted in real-world livelihoods (in fact, many early NASCAR racers were moonshine runners who honed their skills while evading the police on backwoods roads during Prohibition).
For now, boat docking competitions are not televised, and the unique design of Chesapeake Bay deadrises, Virginia’s official state boat, means these competitions are likely to stay local. However, boat docking competitions have gained popularity among boating enthusiasts on social media, with some posts accumulating millions of views.
The Chesapeake Bay even boasts its own social media influencer who has gained worldwide recognition. Luke McFadden, a first-generation waterman from Maryland’s Western Shore, amasses a following of 1.6 million on TikTok. Mr. McFadden, 27, chronicles the working life of a waterman in his videos, teaching viewers how to steam crabs in one clip and how to handle a crab pinch in another. At the St. Michael’s competition, he was constantly hounded for pictures and treated to free beers.
“People associate boats with luxury yachts,” Mr. McFadden remarked. “But this is the true essence, what boats were originally intended for.”
Despite their participation in these competitions, many long-time competitors, like 50-year-old Mr. Ashton, still work on the bay. However, the number of licensed watermen has been steadily declining. A 2016 study conducted by the Federal Reserve Bank of Richmond attributed this decline to stricter government regulations and an aging workforce. Industry executives in the seafood sector on the bay claim they require more migrant workers for crab processing, but watchdog organizations argue that these migrants, primarily women from Mexico, face mistreatment.
Mr. Ashton’s grandparents used to cook and sell crabs on Hoopers Island, but it seems that the life of a waterman might end with him. “None of my boys are interested in it,” he admitted.
While Mr. Reiss works in marine construction, he still engages in oystering during the winter. His 9-year-old protégé, Peyton, aspires to become an engineer. Mr. Jacobs, on the other hand, worked on a tugboat in Baltimore Harbor after high school but left the waterway for a more stable life driving a fuel truck—a factor that prevents him from entering certain competitions with his boat. Mr. Jacobs explained that the costs associated with being a waterman, including fuel, bait, the unpredictable crab market, and the lack of assistance, simply “don’t add up.”
Some watermen have repurposed their boats for tours or transformed them into water taxis, while others have opted to sell them altogether. In St. Michael’s, a woman recognized her mother’s name emblazoned in red letters on the hull of the Kathy Marie, a working boat, and broke down in tears. The boat’s captain promptly disembarked to comfort her.
“That was my daddy’s boat,” she told him.
According to Mr. Jacobs, the prize money helps cover the expenses since being a waterman is a costly endeavor.
