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Standing at the corner of Westminster Avenue and Parkside Drive, it took a moment, but then it dawned on me: While it's of little use today, that teensy-tiny street sign affixed to the side of this High Park home 15 feet up would have been an easy read from a horse-drawn buggy, since one sat much higher and travelled at a more relaxed clip. The same goes for early automobiles, which were based on carriage designs.

My guess is that these housebound signs are the oldest in the city. Allen Pinkerton, 51, manager of Signs and Markings with the City of Toronto, shares that opinion. He also adds that since maintenance of these historic tidbits no longer lies with the city, we can thank homeowners for their continued survival: "Oh yeah, probably a little help from the property owners taking care of it [because] they are unique, very few cities have it."

Think about it: Street signs are one of the few directional markers a city can use to brand itself; they're also a good way for a neighbourhood to distinguish itself within the larger city. Most other signs are of a regulatory nature – stop, yield, no parking, no standing, no left turn, etc. – and, as such, are governed by the province with regards to size, typeface and colour.

So, I went in search of as many vintages as I could find, hoping that they, too, would speak of their era. In older areas, I often spotted multiple vintages within blocks of each other, and at busy downtown intersections I sometimes found two or three layers of signage at the same corner. The simple explanation for this, of course, is that it's city policy to replace signs only on an as-needed basis.

From Yonge and Queen's Quay to Yonge and Steeles and all points in between, the most common marker is the large blue reflective rectangle with white lettering. Usually attached to the metal arm that holds traffic lights aloft, these are the boiled potatoes of signage they're so dull and ubiquitous; while we look at them dozens of times a day, we don't 'see' them any longer.

Up until recently, the much older black-and-white "acorn" signs – made up of a separate metal frame, a painted white face with embossed black lettering and a three-dimensional acorn like the cherry on a sundae – had become almost invisible until the mid-2000s, when the city began replacing them with two-dimensional, laser-cut facsimiles, which, in my opinion, said to out-of-towners that Toronto favoured fiscal responsibility over beauty.

Interestingly, there was a version that came before the laser-cut uglies that dispensed with embossing (too costly) but still featured separate components of frame, sign and acorn. In some areas of the city, one can see all three generations.

Thankfully, opposition to the laser-cut signs brought change: "I think those types of signs were what actually was the catalyst to [trigger] the discussion to create the new signs," Mr. Pinkerton says. Approved in early 2007 by city council, the Kramer Design Associates signs were a complete departure. Featuring a reflective middle blue band with reflective white lettering in the Clearview typeface (approved by the U.S. Federal Highway Administration) there is also a curved top "blade" for neighbourhood branding and a bottom area to provide the closest street address.

While some thought the Kramer signs versatile and modern, acorn-lovers were angry (some created "Save the Acorn" Facebook pages). They look like "anyplace U.S.A." was one online complaint; some criticized the poorly publicized public consultation process; others argued that the tried-and-true black letters on a white field would have better visibility; a few chimed in that Clearview was too thin and reedy. "I'd love Oak St.," laughs Mr. Pinkerton in protest. "Scarborough Golf Club Road – that's a lot of information to put on one sign, and to do that over a 38-inch blade would mean you'd have to start compressing [the letters] quite a bit, where with Clearview you don't need to."

In other words, we'd better learn to love the new font, because it isn't going anywhere.

One type of sign that is fast disappearing is the illuminated box. To my eye, these rectangular 1960s gems were the perfect companion to our rectangular International Style architecture. They harkened back to a time of illuminated telephone boxes and squat metal garbage receptacles. Up until a few years ago, I knew of a handful of intersections where these could be found, but they turned up empty, so I turned to my friends at (a great online resource) for help.

I was directed to the pedestrian island at the north side of Queen and Bay, where I found both a yellow and a blue example on the same pole. At the southeast corner, the illuminated Bay box still has the 1967 Centennial logo on the end.

Obviously, with burnt bulbs and metal boxes that would eventually split open during decades of freeze-thaw, these would have been an expensive nuisance. However, it's just these sorts of things that will make for wonderful urban artifacts at the Toronto Museum … should we ever build it.