It's devilishly hard to keep the list down to ten, so forgive me if I do some cramming and cheat a little:
1. Cinematheque Ontario. Alas, it's not in season during TIFF but this is the place that draws me most to Toronto and I just had to begin with a coup de chapeau to it.
2. Little India. On Queen Street, and probably my favorite Indian restaurant in Toronto. It's quite small, and monstrously popular, so I'd suggest lunch either early (11:30-ish) or late (2:00-ish). For a whole cornucopia of Indian food, I'd recommend a trip to the Indian section of town on Garrard Street East. For about three blocks, you could swear you were in the middle of Mumbai.
3. Bookstores: Andrew Tracy hipped me to this chain called BMV (Books Music Videos) that carries discounted merhandise and tons of it. I've been to 2 locations, one off Yonge near Dundas and the other at Yonge and Eglinton. I also recommend a great used-book shop called Eliot's on Yonge near Wellesley for books on art, film, music, etc.
4. College Street West: Adam Nayman turned me on to this books-and-music zone which includes stores like She Said Boom. I've been here just once and scarcely skimmed the surface. I'll be trying to squeeze in a visit during TIFF.
5. The Beguiling: Seriously: the best indie comics shop I've been to in North America and I've been to a few. If you're an indie comics aficionado, leave your credit card at home and take a budgeted amount of cash. You've been warned. Also, close by is one of the largest video stores in the city, Suspect Video.
6. The Art Gallery of Ontario (AGO). The gallery is only partially open because of construction but it'll be running exhibits of Chuck Close and Bernini during TIFF.
7. The Rex. Top-flight music club hosting the best in local Toronto jazz. Very often, there's not even a cover charge. Good food and beer selections. On Queen St., close to Little India.
8. Two More Great Bookstores: (a) Pages on Queen St., not far from the Rex; and (b) Theater Books, a stone's throw from the Varsity and Cumberland theaters. Great selection of film books at both places.
9. The Film Reference Library. Affiliated with the TIFF group. You can't borrow anything but you can watch videos and DVDs from their large collection (lots of rare and unreleased stuff) and consult books and back issues of periodicals. Recommended from their collection (and unavailable in the US): Claire Denis's U.S. Go Home and Olivier Assayas's Cold Water.
10. The NFB Mediatheque. For two bucks, you can get comfy in a large plush chair/viewing station and call up any of the hundreds of films produced by the National Film Board of Canada. The last time I was there, I caught Gilles Groulx's Le Chat Dans Le Sac (1964). My next trip will likely feature some Arthur Lipsett. Located close to the Scotiabank Theatres used by TIFF.
Your suggestions and tips for fun places to go in Toronto? Perhaps we can build ourselves a little trove of ideas here. Thank you!