The province’s University Lunatic Asylum:
1859 map,
1859 photo.
The park has a cool equestrian statue of King Edward VII, relocated from Delhi. Sit in the shadow of the old King and feel the subway trains rumbling underneath you.
Avoid driving on Eglinton Ave through the central city; it’s all dug up for subway construction. Unless you like looking at big holes in the ground, of course.
If you travel by train, be aware that Union Station is a vast never-ending confusion of construction. They’re digging down under the old station and trainshed and building a mall underneath, as well as tripling the commuter concourses. It’s actually a fascinating feat that involves bracing every support column, cutting it off, digging down to make more room, inserting a new taller column, then putting in two floors where there was previously only one.
But visitors may need a good 3-D map and a team of Sherpa guides to find their way around, especially if they’re trying to get from the airport train to the subway. Or anywhere in the Underground City, but then the Underground City–dozens of kilometres of malls and corridors linking much of the downtown core-- has always been like that.
The airport train comes in from Pearson Airport, the main international airport. Some smaller flights land at the Island Airport, just off downtown. You can walk from its terminal through a tunnel to the streetcar and take that streetcar downtown in 20 minutes. The streetcar goes along Queens Quay through Harbourfront, former docklands that are now festival places and art galleries and theatre and condos. Lots and lots of condos… but it’s a cool place to be on a summer afternoon.
My family went to Toronto for a long weekend in May. Because our weather was awful (30s F and sleeting), we couldn’t do a lot of what I’d planned (mostly, maybe naively for mid-May in Canada, patios and markets), but here’s the list. I’ll have to live vicariously through you!
Kensington Market - Kensington Market - Home
St. Lawrence Market - http://www.stlawrencemarket.com
Yorkville - http://www.bloor-yorkville.com
The Monkey’s Paw, home of Bibliomat, “the world’s first randomizing vending machine for old books” - http://www.monkeyspaw.com
Amsterdam Brewhouse - http://amsterdambrewhouse.com
Distillery District - http://www.thedistillerydistrict.com
The Federal - http://thefed.ca. We went here on our last night there, and this is just one of those places, you know? It had been a long, chilly day, and we were tired and hungry and we just came upon this gem - small but comprehensive menu, great drinks and atmosphere, and staff that made us feel like family. I’d love to go back.
Have fun with your family! Toronto is a wonderful city.
Thanks, all!
If you’re going to Old Chinatown, take the 510 Spadina streetcar to get there. Jog over a block from Spadina north of Dundas to Kensington Market to explore the funky shops. Otto’s Berlin Döner serves great German street food. It’s just down from the marijuana dispensary, if that hasn’t been shut down.
The situation with respect to MJ is confusing. The federal government announced plans to legalize the drug next year, but no details are known. Meanwhile, it is still illegal, unless you have a medical marijuana license, but if you do, you’re supposed to buy from an officially-licensed producer… who ships the MJ to you by Canada Post. So where did all these dispensaries come from? The police were turning a blind eye to them for a while, until a series of warnings and then raids a few weeks ago. I don’t know the status of any of them now.
Exit Kensington Market northwards to College Street, and walk or take the streetcar east to University Ave. You can walk north through Queen’s Park to Bloor Street, the ROM, and the Mink Mile of high-end shops.
The Mink Mile is along Bloor between Avenue Rd and Yonge St. Just north of the Mink Mile is Yorkville, a former bohemian counter-culture district that is now more ritzy shopping and people driving their Lamborghinis around to show off. Last time I was there, it still had a very good ice cream shop and a great French bookstore.
I haven’t seen the fake monks there recently (and I walk by there every day). Currently it’s guys handing out a photocopied “Black History Guide” that they try to guilt you into paying 20 bucks for.
Walk east along Yorkville Ave to Yonge St, and you will find the Toronto Reference Library. I’m not sure why, but one thing that Toronto actually does well is public libraries. You can borrow books in dozens of languages, take classes, do research in person or online, publish your own books, use 3-D printers, all kinds of stuff. Many of the library branches are in absolutely-beautiful buildings. And the online resources are superb. I myself pay to maintain a non-resident membership so I can use them (I don’t live in Toronto at the moment–hoping to get back!) There are also some great special collections: a Sherlock Holmes collection at the Reference Library and the Merrill Collection of science fiction come to mind.
Also at the Reference Library is a comic shop selling comic books, graphic novels, anime, bandes dessinées, whatever you want to call them. It’s a joint venture between the library and the superb comic shop The Beguiling a few kilometres west at Bloor and Bathurst. Both are sponsors of TCAF, the Toronto Comic Arts Festival, an enormous gathering of comics-related sales, lectures, demonstrations, and workshops that takes place every year. This year it took over the first three floors of the library. My friend and I went, didn’t have time to see all of it in the library, and then discovered that there were nine other venues. It really is the TIFF of comics events.
Oh yes, TIFF, the Toronto International Film Festival. Apparently it’s #3 in the world, after Cannes and… another festival I’m not certain of. Takes place in September, and brings all sorts of celebrities to town.
To get to the zoo from downtown without driving, take the GO train to Rouge Hill station, then backtrack a little on the #85 bus. 
But if you are driving, you can go a little further and check out Rouge Park.
I don’t know why this sticks out in my memory, but it does. I’ve certainly passed by it more times than I can count, and I remember a lot of press coverage when the move happened.
A couple of things that haven’t yet been touched on, that you might want to look for if you’re downtown (and that most people are unaware of):
Old City Hall (Queen Street at Bay Street). It hosts law courts today, but look at the outside–see all the faces of the gargoyles? They are caricatures of the city councillors of the day. Seems the City balked at paying the stonemasons’ bills, so the stonemasons memorialized the councillors as ugly and scary gargoyles in retaliation.
Old Stock Exchange facade (Bay Street south of King Street). The Stock Exchange is today a modern facility inside, but the Art Deco facade of the old Stock Exchange has been preserved and still stands on Bay Street. Look for the capitalist in top hat and tails reaching for the worker’s pocket.
Commerce Court North (King Street between Bay and Yonge Streets). This is the oldest building in the Commerce Court complex, and was, at one time, the tallest building in the British Empire. So tilt your head back, and look up–wayyyy up. (Canadians of certain vintage will get the reference.) Look for the 12 four-storey-tall stone heads carved into each corner, and on the sides.
I should also mention, if you like architecture, the University of Toronto (surrounding Queen’s Park, with the bulk of it west of Queen’s Park). The U of T, as it is often called, is a federated university based on the Oxford system. It can be a quiet oasis in the middle of a bustling city, but it is also noteworthy for a few things:
University College: One of the oldest buildings on campus, UC, as it is known, might as well be Hogwarts. Mainly Romanesque, with turrets and cloisters, it also hosts a ghost. During reconstruction after a fire, stonemason Ivan Reznikoff got into a fight with a fellow stonemason over a woman. Reznikoff was killed. A ghost was later reported to be walking the halls. The story was scoffed at, but during renovations many years later, human remains were found inside a wall. Nobody knows if they were Reznikoff’s, but the ghost still walks.
Soldiers’ Tower and Memorial Walls. Right next to UC, the name of every U of T student and faculty who went to World Wars I and II are memorialized in stone. If you are lucky, the little museum over the Soldiers’ Tower arch will be open, or you might hear a carillon concert from the tower’s bells.
Hart House. Very few student centres are as opulent as this. Hart House hosts a number of activities, some physical (two gyms, workout rooms, etc.) and some not so (a library, clubs and classes in various areas, a few eateries, etc.). Look for the photo of JFK, when he was a US Senator, debating in the Debates Room on the second floor, and the signatures of British monarchs in the guest book. For that true Hogwarts feel, have a meal in the Great Hall; or for a more intimate faculty-club-like feel, try the Gallery Club. The Arbor Room, in the basement, is a good place to take a break for coffee and/or snacks. Hart House is a student centre, but it, and its eateries, are open to the public.
And lastly, the U of T is noteworthy because it is where a few Dopers did their undergraduate work. 
Personally, i always like wandering around the Royal York a bit - it was one of the CPR opulent railway hotels.
Stop into the Library Bar, and ask for a pint of Apiary Ale. It’s the only place that beer is offered, as it is a honey beer, made with honey from the beehives that the hotel keeps on the roof.
Why does the hotel keep beehives on the roof? Because the bees help fertilize the vegetables grown in the gardens on the roof. Which vegetables are served in the hotel’s restaurants. Fresh produce, direct from the top floor.
When in Toronto, I always stay at the Royal York. It is a grand railway hotel, and still retains its charm. The staff understand their guests’ needs and wants, and I have always felt welcome there. Getting back to the Library Bar, Michael the barman still remembers what I drink, even though I may not have been there for a year, and he serves it up with a smile and a “Welcome back.”
When I was at Queen’s, the Royal York was running a retro ad campaign featuring reprints from their adverts over the past half-century.
One from the 1930s was: “Queen’s men always stay at the Royal York.” The illustration was of these young gentlemen wearing tweed suits. Delightfully anachronistic!
TIP:
If you go to the CN tower, do yourselves a BIG favour and skip the observation deck in favour of the restaurant. It will save you standing in four different lines (to get up, further up, down and further down!), you’ll get a full 360view as it turns (not so in the observation deck!), you’ll be able to go up and down when it suits you, no waiting, and it will be far, far less packed with people! There will be no cost savings, as its overpriced desserts and tea etc. But it’s a much, MUCH, more pleasant an experience!
See if RickJay is performing at a club somewhere! Seriously.
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By the way, if your credit cards don’t have chips, you might want to get chipped cards before you come. I’ve been starting to see signs in restaurants that they won’t take credit cards without chips, because of fraud concerns. Saw a sign to that effect just today in a Smittys.
And you have passports, right? You didn’t say if you’re flying or driving, but a passport is now required for air travel. I think you can still cross the border by car without a passport, but you may want to check with Canadian Border Service and American Customs.
I don’t know how geeky you guys are, but the planetarium at the University of Toronto is really cool. I enjoyed it immensely.
The Hockey Hall of Fame really should be visited.
There is a cat café on the north side of College just west of Spadina. ������