Kingston arterial streets like Montreal Street and outer Division Street were excellent places for advertising agencies to place billboards. Fill in those vacant lots!
There are several commercially-available billboard kits, and perhaps some of them have changeable signs. But they'll be generic and in some cases, American prototypes. Of course, I'd like to have believable 'Canadian' prototypes. More importantly, just like real billboards, their value is in their constantly-changing messages. And my perpetually short attention span quickly tires of the same ol' billboard message all the time.
For the changeable sign, I print out various billboards (various images scanned or found online, sometimes with local messages added in Microsoft Paint or hand-lettered), then use a tape-runner to adhere the sign onto a piece of thin styrene for stability (top left in above photo). Then I attach two or three analogous strips cut from the magnetic sheets to the back (top right in above photo). This is what holds the billboard in place.
There were even large billboards in Kingston's (now) Hub area, shown in this archival photo from 1952 - billboard for local manufacturer Monarch Batteries:
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