From Footpaths to Freeways (John Shragge/DOH, 1987), covers: Early road tolls, Talbot Road, Toronto–Syndeham Road, Toronto–Hamilton Highway (Lake Shore Road), Queen Elizabeth Way, Highway 401
The Shape of the Suburbs: Understanding Toronto's Urban Sprawl (John Sewell/Univ. of Toronto Press), covers: Expressways of Toronto
Toronto Sketches: The Way We Were (volumes one through eleven) (Mike Filey/Dundurn Press), covers: many topics in and around Toronto.
Toronto Street Names: An Illustrated Guide to Their Origins (Leonard Wise, Allan Gould/Firefly Books, 2000), covers most arterials in Toronto, and several streets.
QEW - Canada's First Superhighway (Robert Stamp, 1997), covers the ideas, designs, and construction of the QEW/Middle Road and Toronto–Hamilton Highway from 1914 to (practically) today
Provincial Highway Distance Table (1989), lengths and intersections along all provincial highways at the time.