Davenport Road is one of the oldest, if not the oldest road in the vicinity of Toronto with a history dating back to the time when the great ice sheets were melting. It was a trail used by Native people and early settlers, and is shown on a map drawn by Elizabeth Simcoe in 1796.

Vaughan Road was privately built by the Yorkville and Vaughan Road Company, in 1850, to open up the farm lands along Dufferin Street in York and Vaughan Townships. Originally Vaughan Road started at Yonge St. and followed Davenport to Bathurst St and thence up to and along the present Vaughan Rd. to Dufferin St and north into Vaughan Twp. Its route was based on earlier trails established by the Native People. It provided the first road access to the triangle of high land between the Davenport Escarpment on the south, and the Cedarvale and Nordheimer Ravines to the north-east.

Poplar Plains Road and its continuation north along Forest Hill and Old Forest Hill Roads are very likely based on an old native trail. I can picture this trail north of the Iroquois Bluff being used by Palaeo-Indians to move from their fishing activities on Lake Iroquois to the Mammoth hunting grounds around the marshy ponds along the early Yellow Creek. Poplar Plains Road was known as the "Road to Yonge Street" as 18th century traffic avoided the difficult part of Yonge Street between Davenport Road and The Second Concession North of The Bay (St Clair Ave.), crossing Castle Frank Brook and up the Iroquois Bluff. Old Forest Hill Road was also known as the Serpentine Road.

Thanks to Terry McAuliffe, The Community History Project and others for this information.