Chesapeake Cowboys: The Extreme Sport of High-Speed Boat Docking
Photos by Owen Burke
Dockside on a Friday evening in September with a light but unmistakable northwesterly whispering the beginnings of fall in Chincoteague, Virginia, an elite handful of Chesapeake crab-skiff helmsman is assembled with their respective families and crews at The Pearl, a down-home seafood joint as emblematic of the region as any.
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“Imma f*** you up tomorrow,” roars one captain to another across a full table in a packed barroom, received with raucous laughter. He’s referring to the next day’s high-speed docking contest, in which solo and tandem competitions are held to exhibit the boat-handling prowess of Chesapeake’s premier skippers, six of whom are due to compete tomorrow. Due to a looming hurricane, several regular competitors had to withdraw.
The captains, their crew and their families are all sharing a healthy evening’s dinner comprised of fried this and that: green tomatoes, cheesy crab pretzels, Eastern Shore egg rolls and loaded french fries smothered in crab meat—you get the picture.
The kempt and unkempt alike make up the dining room: Xtratuf deck boots adorn the floor along with Huk, Guy Harvey and Grundéns apparel—a veritable rhapsody in designer waterman-wear if there ever were one. Yet there is also the fine-clothed crowd: Sperry topsiders, Polo shirts, Tommy Bahama. The gathering is a mishmash of Eastern Shore locals and regulars, to whom ice buckets of fine wine and pitchers of cheap beer are purveyed in almost-even procession.
A one-man band is playing classic rock covers, enrapturing the predominantly baby boomer audience: Bob Dylan, Van Morrison, Little Feat and of course, Buffett. There’s a lull after one tune, at which point one of the crab-skiff captains screams at the performer: “I love you,” and you could tell that regardless of how much alcohol may or may not have been pulsing through his veins in that distinct moment, he means it.
The next day, I arrive as the show is setting up. There’s a fire engine hoisting Old Glory from its cherry picker. Trays filled with jello shots in plastic ramekins are making the rounds faster than they can be replenished. The crowd is already half riled, and a DJ is blaring music across the channel. A particularly eager group of spectators is building in number atop a barge for front-row seating atop folding chairs, and perhaps a propeller-induced soaking, about which they’re warned at the head of the gangway down to the premier viewing platform.
Erik Emely, the organizer of the Chesapeake Cowboys docking contest, and my fixer, greets me in the middle of the melee at the entrance booth. “Whatever you need, I got you buddy.”
No sooner does Emely finish offering his services than one of the competing captains, John Ashton, walks by. Emely grabs Ashton by the arm and introduces us before asking John if I might board and photograph from his 1978 41-foot Oneal Jones (recently glassed-over) wooden hull, the Miss Julie, for the day.
A firm handshake and a wave toward the dock grant me access to where the captains are gathering and shooting the proverbial scuttlebutt. Some of the boats are crowded with friends and family, and I wonder whether the extra body weight–and obstacles–might not slow the skippers down some. Then again, I wonder how seriously they take this thing. Do they really care?
I ask Ashton, a former commercial crabber, whether he tossed in the towel when operations got too expensive and the price fishermen fetch for crab became too low. Yes, crab at your local fishmonger might be at an all-time high, but that doesn’t always trickle on down to the man or woman who plucked them from the bay. It’s a familiar story from within the commercial seafood industry. Being of retirement age, Ashton says he chose to hang up his pots, but still dabbles in commercial striped bass (“rockfish” in Chesapeake dialect). The way he tells it, he fishes more to keep busy than to bring in revenue, as it’s no secret that their industry is also currently in decline.
Some of the other skippers are still crabbing though, he tells me, but more and more serious interest is being given to the Chesapeake Cowboys events, especially as a younger crop of competitors arrive on the scene. What started, more or less, as a one-off of salty watermen performing party tricks for waterfront bar patrons has now grown into a full-blown summer tour with 13 stops and more planned for next year. Some teams are already earning sponsorships and are hoping to create a full-time occupation with the competitions. Many of the boats bear decals that might festoon a NASCAR Chevy.
Lest you take all this too much in jest, consider that the event actually bears some real legacy: The first Chesapeake boat docking tournament took place in Crisfield in 1971 during a crab festival. The event has carried on in some form or another ever since. In more recent years, social media has given the series a prodigious boost in interest and attendance; audiences often number in the thousands. One YouTube channel called Extreme Boat Docking solely follows and publishes content about the Chesapeake Cowboys—and has garnered over 85,000 followers. People have made livings in stranger and sillier social-media niches. Just ask Kim Kardashian.
Realizing that there are potential livelihood opportunities for these captains as they queue up to compete, I muster a newfound admiration at the spectacle. For what it’s worth, I’ll gladly watch (and hear) crab-skiff engines groaning full-bore in reverse over, say, a scrum of stock cars rallying round and round a circular track hundreds of times.
On this early fall Saturday afternoon, the Chincoteague crowd numbers in the hundreds—formidable attendance considering it’s shoulder season on the Delmarva peninsula. Further still, a tropical storm has just blown through and another one is headed our way. Apart from the several boats that have pulled out, it’s easy to imagine that more than a few would-be spectators have aborted their trips, too.
Still, there’s fanfare all around, and some attendees—a few of whom you might venture to call devotees—go so far as to pledge allegiance to one captain or another. Captains John Ashton, Jamie Marshall and Danny Haddaway are longstanding stars of the event. Newcomers are making headway, too, and none so much as 18-year-old Sidney Hughes. She’s a boisterous, bling-clad, platinum blonde with a thick and proud Eastern Shore twang who, as of the middle of this season, captains her own boat. She’s called Wild Child.
As competition time nears, the captains suddenly seem to turn from lighthearted jokesters to deeply itinerant contenders. Eyeing the course, checking the tides, considering angles. “The factor here is the tide,” Jamie Marshall says into John Ashton’s ear from over the rail of his skiff. “I wanna zig zag between them [pilings],” he proclaims, drawing an imaginary line with his finger.
“I think we ought to do a practice run just to see,” Ashton replies.
“When you’re going fast, it’s tighter than you think,” Marshall warns, again drawing another imaginary line between the pilings along the course.
And that’s to say nothing of the scores of vessels lining the channel, joining in on the reverie from the water. Jon boats, center consoles, pontoons and cuddy cabins sprawl out about as far as my eyes can see, anchored, spot-locked, or idling. Many are brazenly bearing various flags—many inflammatory beyond family-friendly comprehension at this heavily family-oriented gathering—indicating affiliations political and otherwise.
Just as I start to wonder whether this jumble of boats might cause too much congestion, a couple of anchor lines cross right beside Ashton’s boat. There’s a bit of confusion between the two boats—most of whose passengers are preoccupied with beverages in hand. Rodes are badly intertwined, and it takes more time than my concentration allows to correct the situation.
There’s now an emcee rallying the crowd for “The Star-Spangled Banner,” which is emphatically received by all. There’s not a second spared after the final sustained note, at which point the first vessel is announced.
Each boat takes its turn vying for best course time, with two solo rounds and two tandem rounds. Round one is the solo division: one skipper, four dock lines to be “made.” In truth, the vessels’ dock lines are tied off to industrial-strength hula hoops, which are tossed over pilings to form a makeshift dock. This is brilliant masterminding. Nobody wants to watch someone tie cleat hitches during a race against the clock, much less from any measurable distance. The hula hoops also enable certain theatrics. A crowd favorite: When a vessel is a little too far from the piling for the hula hoop to be tossed with confidence, the skipper (or their mate, in the case of the tandem division) will leap from the rail in a Hail Mary attempt to slam dunk the ring onto a piling before plunging into the soup. We’ll see one or two such displays of diving heroics by the end of the event.
The first skipper idles behind a starting line, standing at his auxiliary helm station, hands over head to indicate the boat’s in neutral. A foghorn blows and the throttles are hammered. Black smoke billows and, with typical diesel lag, it’s a long moment before the boat is up on plane, sending vicious wakes freight-training across what are normally exclusively tame, no-wake waters.
It’s our turn now, and Capt. Ashton putts us over to the starting line and locks us in neutral. I’m standing amidships just forward of his 3208 Cat diesel—the most common engine in the running—trying to station myself in a way that my face (and the two cameras in my hands) won’t meet the transom the second he puts the hammer down. Lit cigarette in mouth, Ashton throws us into gear not a millisecond after the foghorn sounds and black diesel smoke floods my view off the stern, seemingly before we move an inch. Luckily, I realize in this instant that these engines aren’t hot-rodded and the startup inertia is gradual enough as to not take my feet out from under me. We draw a deep S-turn out and around a no-wake sign, which leaves me chuckling. By the end of that S-turn, we’re facing the pilings transom-to, and Ashton’s quick flip into reverse nearly catches me off guard. More black smoke and wake over the transom means we’re coming in hot, and Ashton tosses the forward lines tidily, then barely misses one of the aft lines before re-tossing and keeping us in the running. Looking around at other vessels where crews are more numerous and “beverage indulgent,” I’m glad to know that Ashton’s vice of choice is merely a cigarette.
Hughes’ Wild Child, the only boat running on gasoline, is after us. The crowd shows voices support in high volume as she takes up starting position, hands held high. When the gun goes off, it’s obvious her boat is faster—but perhaps more unwieldy—than the others, heeling over dramatically. Still, she’s quick in reverse and wastes no time landing the hoops in their places, taking an early lead. A flex of the biceps toward the crowd and she’s back to the channel beside us to await her second turn.
Toward the end, as the competition comes to a head, some friendly but pointed mugging between captains raise the temperature a bit, if only for theatrics: Monkey faces, prancing and shirt peeling ensues, but the show concludes in peace.
In the end, the Miss Julie crew suffers a couple of unfortunate tosses, leaving us well out of the running toward the end, but a long, affectionate embrace and kiss from husband to wife ameliorates the sting some, and the crowd eats it up.
Ashton brings me back to the dock, where, after making my way up an aging, questionable gangway, I meet Sidney Hughes’ grandmother in the parking lot after the event. She’s effusive with pride, even donning a shirt bearing her granddaughter’s likeness. Grandma tells me Sidney works at a marina most of the time, but is gaining momentum on the high-speed docking circuit with sponsors and a following to boot. We don’t get far into conversation before Hughes walks up and a fan interrupts us, asking where they can procure one of her signature “Dock Like a Girl” T-shirts. Hughes offers the one off her back, jokingly, before recalling that she may have one in her trunk. No matter how many representatives or sponsors you may have, familial support is tough to beat.
The Chesapeake Cowboys’ extreme docking season would conclude the following week on Tilghman Island, Maryland, with what looked to be a much, much larger crowd in an even tighter waterway.
What’s next for these competitions? Well, extreme boat docking’s organizers have their sights set on a wider tour that would include stops well outside the region—perhaps even a television show. Some captains and crews will surely be patching holes and scrapes and laying on new paint while others will be repairing drive shafts, propellers, and other mechanical bits and pieces not designed for such abuse. But that’s just the price of entry. Others, like Hughes, will be straight back to work. Some veterans, like Ashton, will take a heavy breather. But then peak rockfish season is just around the bend, and the fish will soon come calling. Oh, to be a Chesapeake Bay waterman.
This article originally appeared in the January 2025 issue of Power & Motoryacht magazine.
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