It was the fall of 1997 and Josh Cohen and Sam Shropshire were at Rams Head Tavern in downtown Annapolis discussing the impending—if temporary—closure of the bridge over Spa Creek for repairs. Erected in 1946, the bridge connects the village of Eastport to downtown Annapolis, and its closure would leave the Eastport peninsula almost completely isolated.

“Sam and I were just brainstorming goofy ideas about what if Eastport seceded from Annapolis,” recalls Cohen, who would serve as mayor of Annapolis from 2009 to 2013. As amusing as the idea was, Cohen figured it was just talk, but Shropshire wouldn’t let it go. He rallied support and, a few weeks later, the Maritime Republic of Eastport (MRE) was born.

The impish act of defiance suited the community, which has only been part of the capital city since 1951 and still views itself as culturally distinct from Annapolis. “It’s a deck-shoes and shorts kind of a culture,” says Jefferson Holland, a longtime Eastport resident who served as the MRE’s “Minister of Propaganda” during its formative years. “We like to think of ourselves as underdogs.”

The friendly rivalry soon found an outlet in the Tug of War, a tradition that marks its 18th occurrence on November 7.

“[Shropshire] was talking to [then-Annapolis Mayor] Dean Johnson, and, in a tongue-in-cheek moment of bravado, challenged the mayor to a tug of war across Spa Creek,” recalls Cohen of the contest’s origin.

But there was a problem: A rope of extreme length, strength, and buoyancy would be necessary to withstand the strain that teams of tuggers would exert on it from their positions more than 1,500 feet apart on opposing banks of Spa Creek. But thanks to some clever NASA engineers, a design was soon in hand.

That’s where another MRE founding father, Chris Kellogg, came in. He convinced an executive at Yale Cordage, the venerable rope-making company, to manufacture a rope to those specs and then donate it.

“If we had paid somebody, it would have cost tens of thousands of dollars,” says Cohen. “Without that rope, it never would have happened.”

Now, organizations and businesses sponsor teams of tuggers, raising money for charity. MRE Ambassador to Cyberspace Elvia Thompson estimates the Tug has raised more than $100,000 since it began.

Thompson is part of a new generation of civic leaders overseeing the Tug, but the old guard remains proud and invested, if not quite as involved.

Holland will be there this year, playing his baritone ukulele with Them Eastport Oyster Boys, but you won’t catch him gripping the rope. “I’m not that crazy!” he cracks. “People come off that Tug shaking. It’s a massively strenuous event.”

Shropshire, who now lives in Saudi Arabia, won’t be there, but sent an email saying, “The MRE forces are fully capable of taking on the Annapolis insurgents.”

Cohen, who moved from Eastport to West Annapolis in 2011, will likely take his two young daughters. “It’s become such a tradition,” he says. “It should be on the bucket list of any Annapolitan.”