The Pilot Toronto

Image by Mauricio Alas Photography

The Pilot – Landing for a drink and Jazz

I found The Pilot quite by mistake. You see Ernest Hemingway, the writer, used to hang out in Toronto back in the early 1920’s and I was looking for the watering joints where he used to habituate (more on that in future articles) and I had heard The Pilot was one of his spots.

So, I get there on a Saturday, and to my surprise I found a room full of regulars enjoying an afternoon of jazz with beer. So I stayed. Yet, later, I found The Pilot had opened in 1944 so thus it’s chronologically impossible for Hemingway to have habituated it. Either way though I ended returning again, and again, and again. 

The Pilot is a three storey bar with a spacious rooftop patio, great for a relaxing sunny afternoon plus there is live jazz on Saturdays starting at 15:30 until 18:30. Always worth visiting anytime if you want to take a break from exploring but if you get a chance, check their website, check who will be playing and drop by. Just remember, you come here to enjoy listening to jazz, not to speak over it. So wear your jazz appreciation hat! 

Also, if you get the chance, say “Hi” to Masoud, the low-key but always friendly bartender. His name means ‘Happiness” in Persian and he is himself an institution and part of the bar since 1985! If he’s not too busy ask him and he might tell you a few really great stories. More than a few are really good.

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Details about this spot



22 Cumberland St, Toronto

Telephone number


Opening Times

Mon - Fri 11:30 - 02:00, Sat 12:30 - 02:00, Sun 14:00 - 02:00


Beer (pint): C$ 7.50


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Last Changed Date: 2016-05-19 11:45:13 +0200 (Thu, 19 May 2016)