Davenport Road is one of the oldest streets in Toronto. Some 12,000 years ago it was a meandering trail along the shore of Lake Iroquois first used by native hunters and traders. After the shoreline receded it continued to be an important overland link between the Don and Humber rivers. It is one of the few major streets in the city that is off the grid as it follows the original pathway.
Settlement along the area of the road, located below a steep hill, began in the mid-19th century.
In the 1850s, the old Indian path at the base of the hill was widened and called Davenport Road, after the village of Davenport, which was established near Davenport Road and Symington Avenue -- west of today's Regal Heights neighbourhood. Although originally improved by the colonial government, for many years during the 19th century the road was privately owned and people using it had to pay tolls. The 1830s cottage of the toll keeper at Bathurst Street and Davenport Road survives and is located in a park at the northwest corner of the intersection.
Travel on Davenport Road was not easy in the 19th century. A grandson of Bull described the road as "an epic of mud." Davenport Hill was a challenge as well. Locals used to observe that horses tired from pulling wagons along muddy Davenport Road would drop to the ground at the thought of having to pull a load up the hill.</i></blockquote>
Many toll booths were set up along the road. Even now, a booth exists, preserved in a park at the intersection of Bathurst and Davenport.
Guess where I went walking and photographing one fine bright Sunday day?
At the end of Spadina Road at Davenport, a steep flight of stairs leads up the hill to Casa Loma, Toronto's only castle.
George Brown College's Casa Loma Campus does have some sights, industrial though they may be.
The houses on the north side of Davenport cling precariously to the side of the hill. I like this.
See the Wikipedia Commons for some historical photos of Davenport Road.