Toronto's extensive work on the silver screen reveals that, while we have the chameleonic ability to look like anywhere from New York City to Moscow, the disguise doesn't always hold up to scrutiny. Reel Toronto revels in digging up and displaying the films that attempt to mask, hide, or—in rare cases—proudly display our city.
We have to admit we kind of like Fever Pitch. Sure, it's a formulaic rom-com, but it's a lot better than what we typically have to sit through. More to the point, it makes such great use of its Boston locations (particularly the stuff in and around Fenway Park) that you would hardly know how much of it was shot here.
You'd think interiors would constitute most of the Toronto work but, au contraire, they love our parks. Not once but twice does the couple take a stroll through Queen's Park. This is the first occasion, and you can see the statue of King Edward VII in the background.
The second time is for a heart-to-heart/barbecue in the northeast quadrant. You can see Victoria University and St. Mike's in the back there.
Early in the movie is this touch-football game filmed at Withrow Park.
Later, baseball coach Fallon gets some advice from this kid at Connorvale Park.
The production even takes a jaunt down to Niagara Falls during one of those annoying dating montages.
You can't have a modern romantic comedy unless both the male and female leads have a wacky group of friends! In Drew Barymore's case, this includes a trio of ladies with whom she works out at Diesel Fitness' old location on Spadina.
They also go rock climbing at the Toronto Climbing Academy on Broadview.
Later in the movie, one of the friends has this big Great Gatsby–themed party. It's in the St. Lawrence Hall, where Jimmy and Drew find themselves waiting for a cab afterwards.
Jimmy's a teacher (all the better for interacting cutely with children), and while the establishing shot is of what must be a Boston school, the interiors were at Givins Shaw PS.
There's also a scene where he talks with Drew Barrrymore out back, but this scene was done at Western Tech.
They go to a fancy, shmancy restaurant with Drew's parents and, lo and behold, it's the Rosewater Supper Club.
Of course, the great bit of trivia here is that the Red Sox were "cursed" as incapable of winning, but as filming went on it became increasingly obvious they might just pull it off. In the end, the Sox won the 2004 World Series, forcing an on-the-fly rewrite and meaning that hundreds of years from now baseball fans will wonder why the hell Jimmy Fallon and Drew Barrymore got to run on the field during the players' celebrations. And now Toronto gets to share in just a little slice of that; given how this last season went, we might as well take what we can get.
This article originally incorrectly identified two locations: St. Lawrence Hall, which was mistakenly identified as St. Lawrence Market, and Western Technical-Commercial School, which was mistakenly identified as East York Collegiate.

Are you sure that's East York CI? It's a tight screenshot, but it looks a hell of a lot like Western Tech.
I was going to make the same comment. Looking at pictures of East York, it doesn't look similar at all. I think it's the eastern side of the Western Tech/Ursula Franklin building on Glendonwynne. Though there's a plaque in the background of the screen cap in this post that isn't in the Google Street View image of the Glendonwynne entrance.
It could be the entrance that opens out to the sports field. Street View wouldn't have a shot of that entrance (same spot used to kick off the "academic decathlon" in Billy Madison).
I was at a Jays game while this shoot was in Toronto. Berrymore and Fallon were there and I recall someone saying at the game or in a report after the game that there had been some scene shot at that day's game. Any idea if that actually happened/made it into the movie?
One more location....
Some of the baseball scenes were actually shot during a Blue Jays game at the Skydome. I was working as an usher for the Jays on the 200 level of the dome that day and we were well aware that Barrymore & Fallon were on site filming. I'm pretty sure that Boston was in town at the time for the game as well.
Yeah... that's not St. Lawrence Market.
The market building's down on Front Street and has a quite different-looking main entrance. The shot is actually of St. Lawrence Hall, a block north on King Street.
Yeah, I thought St. Lawrence Hall right away too.
It's always interesting to see where they shot in Toronto, I've stumbled many a time onto a film scene here. Ièm mostly enjoying all these clarifications as well. I tried to find an image of the door where the plaque is but couldnt; yet i did find that the main building of western tech was in fact constructed in 1927 which would coincide with the plaque. Green Sulfur, you are correct: http://en.wikipedia.org/wiki/Western_Technical-Commercial_School
re: the potentially misidentified St. Lawrence Market and Western Tech locations—
We're checking that out now and we'll definitely append a correction if we're wrong on both or either.
Although not even close to being an "offical source", having spent 3 years at the George Brown campus on King street, I'm pretty much 100% certain that the shot is infront of St. Lawrence Hall and not the market
Mark, Green Sulfur, John, TokyoTuds, BellaBella: you are all right. The scene that this article said was shot at St. Lawrence Market was shot at St. Lawrence Hall, and the scene we said was shot at East York Collegiate was, indeed, shot at the happily waving site that is Western Tech.
I've appended a correction above.
I love this movie! I don't care what anyone says.
This movie should be called "Jimmy Fallon's Stupid Face".