My thoughts begin with this picture of the Square from Streetview:
They follow by asking these questions:
1) Why do I want to come here?
2) Why do I want to stand here?
3) Why do I want to sit here?
4) Why do I want to stay here?
Want a successful space, answering those questions helps.
Lets compare to a successful space nearby, Nathan Phillips Square:
1) To see City Hall, To see the arches/fountain from Star Trek TNG (LOL); to enjoy the water feature, the farmer's market, take in programming, skate (in winter)
2/3) Lots of room to stand, lots of seats, options for full sun, and part-sun shade, views of new and old City Halls; lots of food vendors lined up along Queen (most aren't good, but I digress)
4) Feels like a people space, animated, lively, good to people watch.
*****
We cannot, nor should we seek to duplicate NPS at YDS.
But we can use the former to inform us on how we might make the latter a better space.
1) The space manages to feel small, without being intimate; and sparse without being large.
I would argue this flaw occurs due to the parking garage, and the canopy; along with the way in which the Square is furnished/landscaped.
The relationship to Dundas in particular, but also Victoria is too cut-off; which would be fine, if you wanted an intimate space; but then you can't have a barren, open central area that feels anything but.
I would therefore argue for removing the canopy. But I think must be tied to other improvements, including to Dundas Street which needs to be brought into the Square.
I would argue for alternative paving materials on Dundas from Yonge to Victoria that connect the North and South sides and make them and the street feel as though they belong to the square.
I would also suggest shifting the Eastbound streetcar stop to the square.
This may seen counter-intuitive, littering the place up w/commuters.
But I would argue that it provides a built-in source of animation (there will always be 10-50 people in that corner of the square.
2) I wouldn't clutter up the space with excess green space, but it does need more seating; and it does need some shade for some of that seating on a hot summer's day.
I would argue for a small number of trees replacing the canopy along Dundas.
The focus should be on quality, not quantity. 4-5 trees, each given copious amounts of soil, irrigation, a planter design which mitigates salt as an issue, and the right species is crucial.
I would argue for Red Oak.
They let a fair bit of light through, while providing shade; (there is the issue of acorns when they get bigger......but its only for a short-period each year).
They also spread nicely, have and have appealing form you can see, plus they turn a lovely shade of red in the fall, adding seasonal interest.
I would likewise replace the trees along the south side; they haven't done particularly well.
I think there should be fewer; and better. Replace in much better growing conditions, as noted above.
But I would also choose something that offers both a different colour/form than the trees on the north, and would allow clear views of the heritage buildings.
If I were feeling ambitious, I might like to see some Beech Trees here, as they retain golden-hewed leaves into the winter.
But they aren't the most urban tolerant, and good ones are hard to get, I think I might just settle for 2, yes just 2 Honey Locust, they can get quite large, but have a transparency about them, and would yield a nice yellow in the fall.
I would concentrate the seating between the trees at the edge of the square, allowing an open, central, programmable space.
3) Getting people to eat lunch here matters. With great respect to Shopper's Drug Mart, they need to leave. That whole face of heritage properties should provide a mix of to-go foods and patios than frame the square on the south and provide somewhere to grab a quick bite to eat.
4) Redevelopment of 10 Dundas would obviously be ideal; but short of the City expropriating that site for the second time, will have to wait. But some encouragement to line the ground level with out-ward facing food retail, big openable windows that bring any interior hubbub out.
5) Finally, create some repeatable, strategic programming. Special events are great, but as their timing and interest will vary, they may not create 'regulars'.
As opposed to a farmer's market; how about a Baker's market? Curated, with a focus on baked goods from around the world. Just once a week, come and sample and buy bread with its roots in East Asia or South Asia; Italy or Syria or France or Brazil.
How about a set-day for acoustic musical performances?
Just a (few) thoughts.