Coboconk is one of Ontario's communities (including Tweed, Creemore, Providence Bay, Port Dalhousie, Rodney, and the ghost town of Berens River) which lay claim to be the previous home of Canada's smallest jail. Coboconk's claim was once promoted on the welcoming sign on the south side of the village. At 4.57 m by 8.84 m, it is certainly amongst the smallest jails in North America. However, the absolute distinction belongs to the jail house in Rodney, Ontario, which measures just 4.5 m by 5.4 m. The jails in Providence Bay, Port Dalhousie and Berens River are also smaller than Coboconk's.
The Coby Jail has 2-foot-thick limestone walls mined from the local quarry. These along with the iron bars remain unchanged since the construction of the jail in 1884. Inside the jail were two cells, in addition to the wardens office. The sole constable of the jail, Joseph Wakelin, was appointed in 1899 and retired in 1922.
Local legend tells of a man named Lee who was locked up one night by the constable, who then returned home. Upon the constable's return, Lee was found sitting beside the jail, with no physical damage to the door or lock. This legend, however, can be attributed to the builder of the jail, Albert Ryckman, who left several bricks in place without mortar with the foresight that should he be caught after a night at the Pattie House, he could simply escape unnoticed. It is said that he made use of this escape route several times over the years.