The route immediately widens from two to four lanes and briefly travels diagonally through the eastern edge of the town, partially along the former alignment of Baldwin Street.

The recreation trail ends at Sanders Boulevard, which stops short of an intersection with Cootes Drive, but features a traffic signal for pedestrians to cross to the university.

As part of a plan to build "dual highways" across southern Ontario, Minister of Highways Thomas McQuesten had instructed his Deputy Minister, Robert Melville Smith, to research the Autobahns of Germany in 1934 and subsequently used this design to develop The Middle Road.

McQuesten also began expanding short sections of Highway 2 in Windsor, Woodstock, Scarborough, and along what is now the Thousand Islands Parkway amongst other places.

It was first publicly announced by the Department of Highways (DHO), predecessor to the modern Ministry of Transportation of Ontario, in late June 1936, and construction began on July 21.

[1][6] A contract was let for the paving of the graded route in April 1937,[7] and the new road—while not fully completed—was opened to traffic on the weekend of September 11, 1937.

[1] The DHO continued to refer to this route as the Dundas Diversion for several years,[8] before designating it as Highway 8D for the first time in the Annual Report for 1940.

[15] Highway 102 remained in place until 1964, when responsibility and maintenance over the route was transferred to the townships of Ancaster and West Flamborough.