You might think boat docking competitions are simply a chance for the watermen to show off their skills, but they are so much more. They are an opportunity for waterfront towns to welcome visitors, celebrate their cultural heritage, and raise funds for the local communities.

boat docking competitions
Photos by Mark Hergan, Deadrise Marine Photography 

For 30 years Erik Emely, who goes by the nickname Flea, has been the MC/announcer at docking contests around the Bay. He tells PropTalk that docking contests naturally grew out of watermen “racing” to the docks to get the best price for their catch. “One waterman would say to another, ‘My boat’s faster than yours,’ and the race was on” explains Flea who adds that organized docking contests began popping up in Crisfield, MD, and Tangier and Smith Islands in the early 1970s. 

In 1994 Flea was asked if he’d MC the docking contests, and he has been announcing, promoting, and organizing such events ever since, first bringing a contest to Salisbury, MD, and then other towns. “At one point we had 18 contests up and down the Bay,” he recalls.

About 15 years ago the moniker ‘Chesapeake Cowboys’ started being used to refer to the hot-shot competitors, who throw their lines around pilings like cowboys throw a lasso. The name has stuck, and the events have gained notoriety. 

Flea wants fans to know about the positive financial impacts that go well beyond a fun afternoon cheering on your favorite captain. “What is important and what a lot of people don’t realize is what happens on the backside,” he says. “The competitors are a close-knit community that stick together. Sure, they love putting on a show and displaying their talents, but the money they raise for local causes is the most important thing for them. I just can’t tell you all the wonderful things that the events have supported over the years. We’ve helped out watermen’s families in need, volunteer fire departments, and so many other local non-profit organizations. And the events help drive economic development in these small, waterfront towns. Large crowds of spectators arrive, watch the boat docking, and go to the local bars, restaurants, and shops. 

The competing boats are almost all classic Chesapeake deadrise boats. All have a single screw inboard. “Remember,” says Flea, “some of these guys are competing in the boat they use to earn a living. If the boat gets damaged, they could be off the water until it’s repaired, so there’s some risk there.”

All competing boats must be registered and have a waterman’s license of some type—fishing, crabbing, or oystering. Some of the boat captains have the next generation competing, too. The events have seen competitors as young as age eight.

boat docking competitions
These events are more than a competition - they are an opportunity for waterfront towns to welcome visitors, celebrate their cultural heritage, and raise funds for the local communities.

Flea explains that some events are mostly for show while others offer bigger prize money. Amounts vary by location but are generally in the $3000 to $4000 range.

Behind the scenes much work goes into preparing for an event. Safety is always a top priority. Event sites must be inspected for water depth, proximity to other boats, dock configuration, and more. Timers are needed. At many venues bleachers are set up. There’s the sound system, and the list goes on. But it all comes together to create a festival-type atmosphere for the fans.

Chesapeake boater, photographer, and SpinSheet Century Club member David Sites, who has attended several contests highly recommends coming out for one. “These events are so much more than docking competitions. There is always a great sense of community fun and a party atmosphere. The fans cheer on all the competitors, but when they young kids are competing, they really get the crowds going.”

This summer more than a dozen contests were scheduled around the Bay. Most will have at least 10 boats competing. Some will have as many as 20. Upcoming contests are listed below. For more information, see the Chesapeake Cowboys Facebook page.

Boat Docking Contests:

  • August 4, Chesapeake Cowboys at Cape Charles, VA.
  • August 11, Chesapeake Bay Watermen’s Appreciation Day featuring a boat docking contest, steamed crabs, and family activities in St. Michaels, MD.
  • August 17, Chesapeake Cowboys in Pocomoke, MD.
  • August 25, Taylors Island at the Slaughter Creek Marina. All proceeds go to Taylors Island Volunteer Fire Company.
  • September 1, Chesapeake Cowboys in Crisfield, MD.
  • September 7, Chesapeake Cowboys at the Port of Salisbury Marina and Brew River Dock Bar in Salisbury, MD. 
  • September 8, Chesapeake Cowboys at Hoopers Island, MD.
  • September 15, Chesapeake Cowboys at Solomons Island, MD.
  • September 22, Secretary, MD, in Dorchester County, MD.

If we missed one, let us know by emailing [email protected].