Hillcrest Drive was originally called Front Street North. Regardless of name, it's a one-block run north from William Street to Delamere Avenue.
Front Street North was part of a plan registered in 1920 for a subdivision called Avon Heights. The plan covered the land bordered by what are now William Street, Hillcrest Drive, Delamere and Guthrie avenues.
The land south of William was dedicated as parkland and is now part of the park on the north side of the Avon River.
The fact that there were two Front streets, one on each side of the river, led to some confusion, so in the late 1950s, Front Street North was changed to Hillcrest Drive. The name Hillcrest was chosen to describe the way the street rises to the crest of the hill that is part of the north side of the Avon River valley. The name was suggested by Mrs. James Hislop, who liked to stand on the crest of a hill, from where she could see the surrounding farms.