The Scarborough Bluffs land formation merges the southern boundary of the area and therefore in the 1960's, city planners who were making obvious reference to this, named the neighborhood Cliffcrest.

The Scarborough Bluffs are a natural legacy that was formed following the last ice age, some twelve thousand years ago.

Archaeological evidence accrue in this area during the early 1900's shows that the First Nations people settled along the Scarborough Bluffs dating back 10,000 years, making this one of the oldest inhabited sites in Toronto.

In 1912 Toronto and York Radial Railway entrenched a station & a park along the bluffs, to bring passengers from Toronto.
When the street car line was close down in the late 30s, Kingston Road was widened to indulge to the automobile age which conclusively led to the residential development of Cliffcrest in the 1940's and 50's.