So you're suggesting expanding the market through the Canary District / West Don Lands neighbourhood?
Perhaps not that far, but something more along the lines of this:
Where the current outline is marked in blue, and my theory of how it could expand marked in red once the corresponding developments finish. This is obv not based in any hard fact except my takes on where the neighbourhood is and how it's changing.
To the best of my knowledge, there's only one road (Cherry St) in this enclosure, and it wouldn't necessarily need to close to pedestrians, just have added precautions from the additional pedestrian traffic crossing the streets. Hell, they could even erect a temporary pedestrian bridge the same way some markets in Europe do. There's still reasonably enforceable 'borders' so the market can manage ticketing, and most of the streetscape in this boundary is pedestrianized in each building's respective development applications.
On the European note, Holiday Markets across the pond are never ticketed affairs, are much more densely packed with a variety of local vendors (not just corporate reputation management). They have lots of people but it's never crowded the same way Toronto's is. They're pleasant places to explore, which should be the goal here.
Expanding the existing market like the above would roughly double its footprint. To
@jxmith_ 's point, I don't think the Winter Village will ever stop as it's a huge revenue generator, even if all the parking in the area disappeared. (To my understanding, Green P will manage some public parking in underground lots in the canary district.) The Distillery District organization seem to be at a real crossroads in terms of where the Village will go next - stay the current size and lose out on a great opportunity, or grow to meet the demand.
Finally, I understand that the industrial chic aesthetic is important for the character of the market, but also essentially all nearby developments are folding in red brick/cobblestone hardscaping anyway, so it would be a pretty seamless integration. It won't be the 'core' of the distillery, but again, a decision must be made to address these insane crowds.
Toronto can't keep going on growing like it has while having the same sized amenities. We should have competing Winter Villages to meet the insane demand of these places, last time I went (2019) it was so densely-packed the crowds were beginning to take on fluid characteristics, not dissimilar to a pre-crowd-crush feeling.
