Middle Island is Canada’s southernmost land mass. Sail to its southern edge, and you’ll find yourself just 150 metres from American waters. Few, if any, have called the 18.5-hectare island a lifelong home. Instead, throughout history, Middle Island has served as a crossroads. 

For at least hundreds of years, Indigenous communities around Lake Erie, including the Haudenosaunee people, ventured to Middle Island’s shores to camp and fish, leaving behind shell-tempered pottery and net sinkers in the island’s bedrock. Later, it was a rumoured way point for Civil War deserters and escaped slaves seeking asylum in Canada.

When the clubhouse, a hotel run by the Middle Island Yachting and Sports Club, opened in the 1920s, Middle Island became an island of indulgence. A retreat for the wealthy folk of cities like Detroit, Toledo and Cleveland, it was also a hideaway for American public enemies, such as infamous gangster Al Karpis, and a place to stash the modern-day equivalent of tens of thousands of dollars in banned liquor during Prohibition.

Though the owners of the clubhouse were American, the keys dangled from the belt loop of a Canadian. Pelee Islander Harold “Buster” Williams won the job of caretaker for the club in the 1920s. 

“He showed me where they hid the liquor,” recalls his daughter, Karen Williams-Foster, of a trip they took to Middle Island together more than 60 years ago. “It was underneath the steps in the kitchen when they knew there was going to be a raid.”

Raids by American officials were expected. So were fines, some steeper than US$1,700 — in today’s dollars — for possessing a single bottle of beer. At night, the clubhouse promised free-flowing alcohol and a chance of meeting lady luck at the craps table or, rumour has it, the notorious Al Capone. On occasion, however, boaters would rock up to find Middle Island dry, its intoxicating goods seized by police. Getting there, and getting home, was often a race against the U.S. Coast Guard or, worse, the FBI.  

Middle Island hosted thousands of people over the more than 10 years in which the clubhouse was operational. But not everyone who visited Middle Island made it home, the old stories of Pelee Islanders and long-yellowed clippings of the Port Clinton News Herald say — those who got on the wrong side of a visiting gang ended up sleeping with the fishes on Lake Erie’s shallow bottom.