Toronto
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A quarter of a million people turn out for the Toronto International Film Festival each September, but unlike some of its movie-screening peers (Park City, say, or Cannes), Toronto is big enough to handle the influx without turning into a mob scene. More than other major festivals, the TIFF is known for its film-literate audiences and its diverse slate of movies. It also marks the unofficial start of the award season (Crash and Hotel Rwanda debuted here).

A ticket to a screening costs about $20; for that price, cinephiles can choose among some 300 movies. The 2007 festival, which ran from September 6 to 15, included Joel and Ethan Coen's adaptation of Cormac McCarthy's No Country for Old Men and Shekhar Kapur's The Golden Age, a sequel to his 1998 film Elizabeth (Cate Blanchett reprising her role as Queen Elizabeth I).

...And While You're There
Already one of North America's great vertical cities (only New York has more skyscrapers), Toronto has become a playground for celebrity architects. In the past few years, Frank Gehry, Daniel Libeskind, Lord Norman Foster, and Will Alsop have come to town to build landmark cultural and educational facilities. A walk through the city's downtown now doubles as a crash course in contemporary architecture.

While you're in Yorkville, the posh area where much of the TIFF takes place, be sure to make time for some window-shopping. Bloor Street is home to the department store Holt Renfrew (Canada's answer to Saks), European designer shops (Chanel, Prada, Hermès), and the flagship location of Toronto native MAC Cosmetics.

For edgier fare, head over to Queen West, a neighborhood dotted with galleries and independent boutiques. Girl Friday (416-364-2511) features local designers—including owner Rebecca Nixon—while Preloved (Preloved.ca) restyles retro pieces into one-of-a-kind fashion statements.

Where to Eat
Fortify yourself for a day of shopping and screenings with brunch at the Prague (416-504-5787). This Czech restaurant in Queen West is a favorite among locals, who come for the dumplings, sausages, and Danishes.

Back in Yorkville, stop by Jamie Kennedy at the Gardiner (416-362-1957)—the Gardiner is Toronto's ceramics museum, and Jamie Kennedy is one of the city's most popular chefs. He uses fresh, seasonal ingredients, so the menu changes daily.

Where to Stay
For prime people-watching, book a room at the sleek Intercontinental Toronto Yorkville (rooms start at around $250 but climb much higher during the festival; 416-960-5200). In September, the hotel becomes an impromptu staging area for celebrity interviews; the outdoor restaurant offers an ideal perch for taking in the scene.

The Drake (from $169; TheDrakeHotel.ca) in Queen West is a bit off the beaten track, but creative types are drawn by its aura of well-curated cool (think mismatched vintage furniture) and art gallery.