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As hip to the jive as the folks of Toronto might be, our liquor laws aren't. Something like this will never exist.
Although, the City of Toronto Act gives The City far more freedom in these areas (if they decide to use them). The question may actually be...how hip to the jive is The City in using their newly afforded powers?
 
^Does the new Act give the city the ability to create cafes on public land? Not only do I see this interfering with Ontario's archaic liquor laws that prohibit a licensed establishment from serving alcohol outdoors without a ridiculous fence, but I see this facing opposition from lefter-leaning councilors (and, *ahem*, the views of a certain magazine that celebrates public space) who oppose the "privatization" of public space.

Of course, having a cafe that sits on sidewalk space is not the same as setting up an ad for Chevy in Dundas Square. The cafe enhances and animates the public realm, rather than deadening or cheapening it, but as progressive as they purport to be, this crowd can be surprisingly provincial and wilfully stubborn when it comes to these things. And they're blinded by their ideology, to boot.

I, personally, would love to live in a Toronto where I could sit on my favourite street with a beer or glass of wine and watch the city fly by uninhibited by barriers.
 
Our liquor laws are indeed archaic and need to be updated. We should already have stuff like this. Perhaps such a cafe could be located near the CN Tower. Then there's that Cathedral Square, currently fictitious, which could be another fine location.
 
The Distillery already has several patios like this - a couple in fairly large squares and a couple of cozier ones...
 
The problem with these in Toronto is that they're dismantled and deserted in the winter, left to collect dirty snowdrifts. They don't do much to animate the street if it's not patio weather outside. I'd like to see things more applicable to Toronto, like fountains that can be converted into skating rinks! Nathan Phillips Square is a happening, lively place during the winter while streets lined with cafes and outdoor patios are abandoned and do nothing more than remind people how much they wish it was summer.

Your post reminded me of Moscow's little outdoor "cafe's", they're in every major park and are owned by the city, most don't sport any awnings (did I spell that right?). They're used all year round, even in Winter, I remember reading a book and licking my ice cream during a nice light snow fall, I would love to see these all over Toronto!

P.S. off topic question, a bit of snow falls on the ground and people here call it a snow storm, I can never tell if they're joking or serious.
 
Though it's neither as large nor as beautiful as this one in Hamburg, I quite like the modest little Second Cup in the former ferry terminal building at Harbourfront, and I find it a perfect re-purposing of that building, even without alcohol.

I would certainly close the street that is called "Dundas Square" to traffice and encourage/force all the businesses there to have huge patios with liquor served. The Hard Rock can stay, but it would need to expand.

I would like to see Soho Square on Queen Street look like this.
 
I totally agree with all your points, archivist.

I wouldn't even mind if they built something like that on NPS, or at least adjacent to it.
 
I agree with Hipster Duck's comments and also pertaining to "private" use on public space. When I was in Europe last I recall thinking if such cafe areas were not only benefitial but actually an essential ingredient of most successful urban spaces. They seem to enhance the use and atmosphere of public spaces both in urban square type, waterfront, and garden/park settings.
 
^Does the new Act give the city the ability to create cafes on public land? Not only do I see this interfering with Ontario's archaic liquor laws that prohibit a licensed establishment from serving alcohol outdoors without a ridiculous fence, but I see this facing opposition from lefter-leaning councilors (and, *ahem*, the views of a certain magazine that celebrates public space) who oppose the "privatization" of public space.
To be quite honest, I'm not sure. The law did give the city the power to change drinking hours, but since it has been passed there hasn't been a peep about it. I would think a dialogue could at least start about licensing non-fenced patios.

As an aside, I find our alcohol rules surprisingly more archaic (or perhaps more enforced) in Toronto than other parts of the province. For instance, simply Dan and I stumbled upon some "Rib Fest" in downtown Peterborough a few years ago and the whole park had been licensed. People were walking around this large downtown park -- which wasn't even properly fenced -- with alcohol in hand. I can't imagine that ever happening in Toronto, although if it did many of BIA-festivals and some of the bigger stuff (ie. Pride) would be much more enjoyable. I've also never had an issue taking a beer into the washroom in other cities like Hamilton, but it was always an issue at Toronto clubs for years.
 
I'd much, much rather see a cafe in the squares that doesn't serve alcohol, than no cafe in the squares. In fact, I'm not sure a liquor licence is that important to the formula. In the Moscow cafes in squares that serve ice cream, do they serve alcohol, too?
 
And then, there's the Capitalist U.S. of A. version of such an architectural gesture...
796px-Apple_store_fifth_avenue.jpg
 

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