"Bobcaygeon" is a song by The Tragically Hip, from their album Phantom Power. The song, which won the Juno Award for Single of the Year in 2000, remains one of most famous and best-loved songs the band has recorded.

The song is about a police officer who meets a woman who lives in Bobcaygeon, Ontario; he sleeps at her house (they have sex while listening to Willie Nelson & drinking wine) and the next morning drives back to 'town' (Toronto) while thinking of 'quitting & leaving it behind'. That night, he is assigned to work the Christie Pits anti-semitic racial riot, which breaks out after a softball game during which one of the teams was primarily Jewish. Although the essence of the song is the love that the officer feels for the woman he has met, as 'in the middle of that riot I couldn't get you off my mind', the song does make several references to Bobcaygeon that could ring true to locals. Firstly, the woman that he is with is construed by the song to live in a rural area; most of Bobcaygeon is rural. Secondly, many references to '[watching] the constellations reveal themselves one star at a time' are made; Bobcaygeon is famous for the success of stargazers situated there as the town is far enough away from Toronto to have a view of the night time stars without the interference of light pollution.

The song is fictious in that it is highly unlikely there really was a police officer who fell in love with a girl from Bobcaygeon the night before the Christie Pits racial riot; however the riot itself did happen and its inclusion in the song is another example of the Tragically Hip highlighting anecdotal parts of Canadian history that many people are unaware of.

Lead singer/songwriter Gordon Downie was asked about the name of the song during an interview on an American radio station; he said that the band really could have used the name of any Canadian town but chose Bobcaygeon as it rhymed with 'constellation.' (Thanks Wikipedia)