Bobcaygeon Bootlegger Busted, 1935

For much of the twentieth century, many communities in the Kawartha Lakes region were dry. From 1916 until 1927, the sale of alcohol was illegal in Ontario, afterwards government-controlled sales were introduced. But Municipalities still had the option to hold a vote to either create or remove restrictions on the sale of alcohol. For many years, it was legal to sell alcohol in Lindsay, but not in most of the surrounding communities, including Bobcaygeon. Some Bobcaygeon residents would travel to Lindsay to buy alcohol or ask someone to pick some up while they were in town. Harry Van Oudenaren, who moved to Bobcaygeon in 1950, recalled, “I remember the young fellas going down there on Friday night and getting 6 or 8 bottles of beer and sitting them in a row there and just gulp one after the other. And then they would drive to Bobcaygeon again.” In that era, drinking and driving was much more socially acceptable than it is today.

Though it was legal to travel to Lindsay to buy alcohol, selling it in Bobcaygeon was a serious offence and the village had its own police officer. For many years, the police had a pretty good idea who was selling alcohol in town, and vehicles leaving the bootlegger’s house were liable to be searched. In 1935, Bruce Freeborn of Bobcaygeon was convicted for “having in his possession mash suitable for the manufacture of spirits, was fined $1,000, or in default six months in jail. Freeborn was taken to the jail.” Interestingly, shortly afterwards, one of the Bobcaygeon hotel keepers caught selling liquor to a minor, but did not have his name published. The charge of selling alcohol carried a sentence of two months. The charge of selling to a minor was punished with a fine of $10 or fifteen days in jail. The hotel keeper chose to serve the fifteen days in addition to the two months, rather than pay the $10 penalty (it was during the Great Depression).