City Cinema: Cult Classics at Yonge & Dundas Square
Location: South East Corner of Yonge & Dundas
Tuesday, June 26th - 9 p.m. - The Adventures of Priscilla, Queen of the Desert
Tuesday, July 3 - 9 p.m. - Dazed and Confused
Tuesday, July 10 - 9 p.m. - Harold and Maude
Tuesday, July 17 - 9 p.m. - Monty Python and the Holy Grail
Tuesday, July 24 - 9 p.m. - The Big Lebowski
Tuesday, July 31 - 8:30 p.m. - Do the Right Thing
Tuesday, August 14 - 7:30 p.m. - The Princess Bride
Tuesday, August 14 - 9:15 p.m. - Labyrinth
Tuesday, August 21 - 8 p.m. - Brazil
Tuesday, August 28 - 8 p.m. - Hush...Hush, Sweet Charlotte
Free Flicks: Rise of the Underdog
Location: Lower Simcoe St & Queens Quay, Harbourfront Centre
Wednesday, July 4 - 9 p.m. - Office Space
Wednesday, July 11 - 9 p.m. - Zoolander
Wednesday, July 18 - 9 p.m. - When We Were Kings
Wednesday, July 25 - 9 p.m. - Napoleon Dynamite
Wednesday, August 1 - 9 p.m. - The Social Network
Wednesday, August 8 - 9 p.m. - Whip It
Wednesday, August 15 - 9 p.m. - Whale Rider
Wednesday, August 22 - 8:40 p.m. - Moneyball
Wednesday, August 29 - 8:50 p.m. - Audience Choice
TIFF In the Park: Screwball Comedies
Location: King & Simcoe, David Pecaut Square
Wednesday, June 27 - 9:15 p.m. - Trouble in Paradise
Wednesday, July 4 - 9:15 p.m. - My Man Godfrey
Wednesday, July 11 - 9:15 p.m. - The Palm Beach Story
Wednesday, July 18 - 9:15 p.m. - Raising Arizona
Wednesday, July 25 - 9:15 p.m. - His Girl Friday
Wednesday, August 1 - 9 p.m. - Mr. and Mrs. Smith
Wednesday, August 8 - 9 p.m. - The Philadelphia Story
Wednesday, August 15 - 9 p.m. - What's Up, Doc?
Wednesday, August 22 - 8:30 p.m. - The Lady Eve
Wednesday, August 29 - 8:30 p.m. - It Happened One Night
Movies Under the Stars at Downsview Park
Location: Keele St & Sheppard Ave W, Downsview Park Map
Movies in the Park - Riverdale Park East
Location: 550 Broadview Ave (map)
Backyard Cinema at the 519 Church St Community Centre
Location: 519 Church St Community Centre
it's not free, the Open Roof Film Festival runs screenings outdoors every week at the Amsterdam Brewery. Films are $15, include a concert before the film and it's a licensed venue.
http://www.blogto.com/film/2012/06/free_outdoor_movies_in_toronto_summer_2012/