Toronto is a beautiful city in spite of itself -- or, rather, in spite of some of the city planners and developers who, supposedly in the name of progress, have torn down valuable elements of the city's architectural legacy. Toronto grew by leaps and bounds in the Victorian and Edwardian eras, which is why there are so many stunning buildings from those times (take a walk around the University of Toronto campus for a quick introduction to the different styles, or the Ontario Legislature and the Old City Hall). However, much of the 20th century wasn't as kind: Clumsy planners plunked the Gardiner Expressway near the waterfront -- making what should have been prime parkland into a wasteland -- and roughly 28,000 buildings were demolished between 1955 and 1975. A few of the buildings that went up during that era were stunners, such as Ludwig Mies van der Rohe's black-glass Toronto-Dominion Centre and Viljo Revell's New City Hall. And although Toronto has its share of forgettable buildings, enough Gothic-inspired ones survived to allow the city to make a convincing stand-in for New York on-screen. The good news here and now: Toronto is in the throes of an impressive architectural Renaissance, from Gehry's AGO to Libeskind's ROM (love it or hate it), Alsop's quirky OCAD building to Jack Diamond's Four Seasons Hotel stunner, and much, much more. If you're interested in exploring Toronto's architectural history, the Toronto Society of Architects runs walking tours from June to September, and the Design Exchange offers year-round programs on the topic.
Looking Sharp -- No building in Toronto is more distinctive than the Sharp Centre for Design. While it doesn't dominate Toronto's skyline the way that the CN Tower does, it's a work of stark originality. Designed by renowned architect Will Alsop, it opened in 2004 to near-universal shock -- and acclaim -- including a Worldwide Architecture Award from the Royal Institute of British Architects. The upper portion of the structure is referred to as the "table top," and its white-and-black checkerboard body stands 26m (85 ft.) above the street on 12 spindly, colorful legs. It's most dramatic at night, when it's lit by 16 large metal lights with blue bulbs. Sadly, it's open only to students of the Ontario College of Art and Design, not the public. Located on McCaul Street, just south of Dundas Street West.
The Big O -- The University of Toronto has some of the most eclectic architecture in the city. Unfortunately, one of the most talked-about buildings is one that you can't get inside: the Graduate House, located at the campus's western edge at 60 Harbord St. (at Spadina Ave.). Designed by architect Thom Mayne, this award-winning building looks not unlike a concrete bunker, and the giant UNIVERSITY OF TORONTO sign only has the last letter visible at most viewing angles, earning the structure the nickname "The Big O." There are many more new and interesting buildings on campus, such as the Leslie Dan Faculty of Pharmacy, with a design much sexier than its name would suggest. Naturally, since the architect is none other than Norman Foster.
Park Yourself Here -- Spadina House is the next-door neighbor of Casa Loma. Between the two is a small but lovely park that is almost hidden by the trees that shade it. Many visitors don't notice it, but locals love it. Grab a bench here if you want to take a breather.