Must-see during Toronto weekend trip?

Since you mentioned eating and architecture, you probably shouldn't miss the Distillery District or a trip to The Gooderham and Worts Distillerywhich largely still operates out of the same building it began operating out of in 1837.

But my favorite area for getting off the beaten path is Parkdale. The nabe used to be a hub for Asian immigrants and in recent years has started to become gentrified, so it's still in that awkward teen stage where it's dressed up but you can still find authenticity. I like Bernard's Filipino Specialties for the lechon plate and Ali's West Indian Roti Shop, although if you ask locals what their favorite roti shop is, you better have time for disagreement; roti is big in this area. Bacchus Roti Shop  and  Roti Lady are other favorites.

You should also try some Canadian aboriginal food, and for that I suggest the very popular Keriwa Cafe. They underwent some flood damage, so please check ahead to see if they have opened back up before you go. They were closed on my most recent trip. www.keriwacafe.ca

If you like art you can support local artists by visiting the most recent exhibits at Gladstone Hotel and The Drake Hotel. In particular, the  Drake General Store great place to pick up cool kitschy souvineers by local artists, and they both feature great people-watching at their bars during late hours. I wrote more in-depth about these hotels here: http://bit.ly/17cVcJ1

There's also Parkdale art walk supported by the neighborhood association that takes you by some great street art, cafes and interesting dives. It's a great look at one of the more varied, blossoming neighborhoods in Toronto: www.meetup.com/heartarts/events/128999702/

Kensington Market and late night drinks at Cold Tea ... Brickworks Lane on Saturday morning. Leslieville for cool shopping and Udupi Palace in the Indian Bazaar for great Indian food, La Carnita in Little Italy/college street for great Tacos. Smoke's Poutinerie for , well poutine!

Travel well!

Kensington Market, Guu Izakaya, O. Noir, Barberians Steak House, Yonge and Dundas Square

Lived there for 10 years, these are the more authentic places to go to from a locals perspective. I'm not sure about clubs though.

If you're looking for a popular, non-Asian restaurant in  Parkdale, I can suggest  Local Kitchen & Wine Bar, 1710 Queen street west (sorry, not yet in this database).  It's part of the slow food movement and so they only use local producers.  Very popular with the local crowd and has been growing steadily since they opened a few years back.  Make reservations... and try their salumi :)

Well for architecture you must check out the  Royal Ontario Museum for a gorgeous museum near Yorkville (our fancy neighbourhood), the  Distillery District for the only cobblestone walking streets in the city. El Catrin is an amazing Mexican restaurant in the district.  Casa Loma is a gorgeous castle in the city as well. In terms of clubs what are you looking for?

Kensington Market Neighbourhood. 

Between College and Dundas, and Spadina and Bathurst. 

These are all great suggestions.  For food, I would also check out  California Sandwiches in Little Portugal and order the veal Parmesan.  Best sandwich ever.  For the weekend, and if you want some good Indian food, go to Gerrard Street and go to any of the restaurants.  My favorite is  Lahore Tikka House that has great kabobs.

As for sites, check out the  Hockey Hall of Fame and grab a drink at  Earls Kitchen & Bar

Thank you to everyone who offered suggestions (and to anyone who might in the future)! I really appreciate the help. Can't wait to visit and check out everything you've recommended. :) 

Though the chances are probably slim, if you ever find yourself visiting -- or wanting to visit -- Rochester, NY, I'm more than happy to offer suggestions of my own.

Happy travels!