In the first half of the 20th century, Manitou Road was the main commercial street of Centre Island. Originally known as Middle Road, it became an increasingly important thoroughfare with the construction in 1905 of a freight wharf near the bridge over Long Pond. To serve a growing population of both summer and year-round residents, business along the road expanded in the following decade to include a general store, a butcher shop, a dairy, a boathouse, laundries, and several hotels. Manitou Road also became an entertainment hub with facilities that included a casino, a bowling alley, and a movie theatre.
In 1956, Metropolitan Toronto Council expropriated Centre Island for the creation of Toronto Island Park. Many of the businesses were demolished and Manitou Road was replaced by a concrete pedestrian walkway. Known as the Avenue of the Islands, this walkway evolved into a grand boulevard, lined with sculpted trees and hedges, colourful flowerbeds, and reflecting pools.