The Cliffcrest neighbourhood was named in the 1960's by city planners who were making obvious reference to the Scarborough Bluffs land formation that skirts the southern boundary of this neighbourhood. The Scarborough Bluffs are a natural wonder that was formed following the last ice age, some twelve thousand years ago. Archaeological evidence gathered in this area during the early 1900's shows that the First Nations people established settlements along the Scarborough Bluffs dating back 10,000 years, making this one of the oldest inhabited sites in Toronto.
The Toronto and York Radial Railway established the sixty acre Scarborough Heights Park on the crest of the Bluffs in 1912. This park was created for business purposes by the railway in order to attract more passengers to their line. Scarborough Heights Park closed in 1929 and the streetcar line was discontinued in 1936. Following the dismantling of the streetcar Kingston Road was widened to cater to the automobile age which ultimately led to the residential development of Cliffcrest in the 1940's and 50's.
Cliffcrest is a family oriented community that looks and feels more like cottage country than a big city neighbourhood. The lushness and natural beauty of this area emanates from the spectacular Scarborough Bluffs, whose towering sandy cliffs peer out over the Lake Ontario shoreline.