Back That Boat Up

Rachel Dean captains the Roughwater. Photo by Molly Weeks Crumbley.

Extreme Docking at the Watermen’s Festival

By Molly Weeks Crumbley

Sunday, Sept. 19 was a warm day on Solomons Island. The sky was cloudless, seagulls and the occasional bald eagle wheeled overhead, and throngs of people trooped down sidewalks and roads towards their destination: the 20th Watermen’s Festival and Boat Docking Contest. After a yearlong hiatus due to the pandemic, anticipation for the festival was palpable in the little town. As the crowds filed in to find their seats on the bleachers at Fisherman’s Wharf, they were greeted by Deanna Dove, singing her heart out. “It’s a peace, love, and crabs kind of day,” Dove, also known as the Island Girl, warbled to applause. “Oh, and beer.” Even more applause.

As the noon hour approached, the stands overflowed with people (and dogs) from all over the area, some giving up on finding seats in favor of staking out spots on the gravelly ground to perch upon. “Folks, it is going to get exciting today,” enthused Dove. “Biggest time of the year in Solomons.”

As the boat captains readied their craft for competition, Dove slid into a rendition of “Sittin’ on the Dock of the Bay”. The gathered onlookers swayed and whistled along appreciatively, many clad in the bright yellows and reds of the Old Bay logo and the Maryland flag.

JoJo Ruark takes first place in the large boat contest. Photo by Molly Weeks Crumbley.

Though the festival featured attractions like buoy and anchor tossing contests for the kids, tents selling local food and drinks, and auctions and giveaways, the jewel of the whole affair was easily the boat docking contest. For the uninitiated, extreme docking carries the excitement and spirit of a rodeo—with a splash. The Chesapeake Cowboys organization, which holds contests around the Bay area each year, explains that extreme docking is “considered a water sport in which work boats and charter boats compete within their divisions to go from point A to point B and lasso poles in a timed competition.”

The work is fast and furious, the turns are hairpin, and the water is rocking with more than a few boat-made waves. It is also much, much harder than it looks.

Even experienced watermen miss their ring targets or even crash into pilings in the heat of competition—occurrences that bring forth screams of excitement from the audience. Each captain gets two chances on the docking course, and all four rings must be lassoed to posts for their time to count. Accuracy and speed are both key ingredients in this watery dash, and the thrill of the race to dock against the clock attracts “cowboys” from all over the region.

Competition was close across the categories, each of which had at least three captains entered. Ryan Kastel, captain of the Kastel Bros out of St. Michaels, took first place in the small boat runs, managing to back his boat up in a mere 17.09 seconds. With a break midway through the second run to repair a pole that snapped during the frenzy of the docking, the medium boats were able to finish their runs. Jeff Brown, captain of the .38 Special out of Quantico, was the winner with a 23.91 second run. Notably, of the four boats that competed in the large boat category, three were last minute entries that didn’t even get a practice run. Rachel Dean, secretary of the Calvert Watermen’s Association that hosts the festival, Jason Williams, and friend Mitch Lake weren’t originally supposed to compete, but they gamely joined after discovering that only one boat had entered in the large class.

Spectators gather at Fisherman’s Wharf in Solomons. Photo by Molly Weeks Crumbley.

“We made a pact to put on a show,” explained Dean, and the trio rushed to get their boats during the opening ceremonies. The crowds went especially wild for Dean, who is a well-known schoolteacher in the area. Chants of “Miss Dean! Miss Dean! Miss Dean!” filled the air as she approached the start on her boat Roughwater.

Despite having no practice under her belt, Dean was ready to go. “I didn’t have time to get nervous. There was no thinking,” she said. Her first run of 41.53 seconds was her fastest, but it was her second run that meant the most.

“I was giving too much love to the crowd, being a ham, and got a little silly on the throttles. I wasn’t going to beat my first time, and thought I might throw in the towel. Everyone in the crowd saw me pause and make a mental decision to keep going,” she remembered. Though she ultimately came in second behind JoJo Ruark, captain of the Next Generation out of Hoopers Island, Dean couldn’t be happier.

“The love I got from the fans in the stands for taking a chance and pushing through was incredible,” said Dean. “Even better, there were kids in the stands who watched me keep going, even when things got a little sideways. Their faces said it all.”

Speaking of kids, the last category in the docking contest featured three youth captains, all under 18 years of age. Patrick Bolton, captain of the Side Piece out of Deale, took home first place honors in that category.

The next extreme docking event in the area is slated for September 26 at the Suicide Bridge Restaurant in Hurlock. The contest begins at 1 pm and information is available at and on Facebook @chesapeakecowboys.