The Kingston Road was an Indigenous Trail, a “Moccasin Highway”, surveyed by the British military and minimally improved. It’s chief purpose was to allow troops to move quickly as an alternative to sailing on Lake Ontario. From 1815 to 1817 local settlers built the Kingston or Front Road on a new alignment, closer to the lake, not following Danforth’s trail. Isaac Secord was one of those who took the lead in building the Kingston Road (also known as the Front Road). Isaac Secord was a descendant of the Huguenots who fled from France after the Revocation of the Edict of Nantes (1685). The Secords were United Empire Loyalists, fleeing to Canada after the Revolution. Isaac repaired the road for $1,100. In 1817, the first useable road between York and Montreal was completed. Then weekly winter stage coach service began between York and Kingston.
In 1791 Augustus Jones surveyed the Toronto area again in preparation for settlement. In Leslieville the Crown performed the first subdivision of land when it surveyed the area into long 200 acre farm lots that stretched up from the Kingston Road trail to the what is now Danforth Avenue. The British surveyors laid out the basic grid pattern of concession and sideroad with farms stretching north-south. The Leslieville area was surveyed in a basic plan with side roads with five lots of 200 acres between. Surveyors laid out a First Concession with a Baseline, from which they could plot the rest of the survey. The baseline ran from east to west near the lake. Kingston Road (now Queen Street) runs roughly where the surveyor’s Baseline was. The Don and Danforth Road became the Second Concession Road. St. Clair Avenue was the Third Concession Road.
From 1799 to 1801 an American contractor, Colonel Asa Danforth, built another road, the Danforth Road, the “back road” north of the Kingston Road, “the front road”. It was 16 and half feet wide on a right-of-way 33 feet wide, from York to Kingston, for a price of $90 a mile. Danforth’s labourers were each to receive 200 acres of Crown Land as well as their wages. However, the Government of Upper Canada, not satisfied with his work and perhaps suspicious of his mostly American workforce, refused to pay him, leaving Danforth embittered and a trail unusable for most purposes. His road took quite an irregular route since it followed a Mississauga trail. Danforth Road came up King Street, crossed the Don on Scadding’s Bridge (where the Queen Street bridge is now) and followed a fairly straight line eastward through a pine and oak forest on the sandy plain north of Ashbridge’s Bay, to the long hill up Kingston Road at Woodbine, where it dog-legged north east. This, like most roads of the time, was a mud hole in spring and fall, passable only in a dry summer and, by sleigh, in winter. It was finally the Don and Danforth Plank Road Company who built Danforth Avenue in 1851 connecting it to Broadview Avenue.
Captain Basil Hall, in 1827, described travel on the Kingston Road:
The horrible corduroy roads again made their appearance in a more formidable shape by the addition of deep, inky holes, which almost swallowed up the fore-wheels of the waggon, and bathed its hinder axle-tree. The jogging and plunging to which we were now exposed, and the occasional bang when the vehicle reached the bottom of one of these abysses, were so new and remarkable in the history of our travels that we tried to make a good joke of them.
In 1830 William Weller began operating the first regular stage coach between York and the Carrying Place on the Bay of Quinte, passing through the little hamlet of Ashport, named for the Ashbridge’s Bay. In the 1830s crews planked the Kingston Road for 18 miles to the Rouge River. The plank road became a toll road. Villages sprang up at the toll gates along the road — Norway at the Woodbine toll gate; and Ashport (later called Leslieville at the south west corner of Leslie Street and Queen Street); and Don Mount (later renamed Riverside) at Mill Road (now Broadview Avenue). The road was still very rough:
By land there are only two seasons when you can travel with any degree of comfort, –midsummer and midwinter. During the former part of the year, travelling on horseback is preferable, or in a light waggon—during the latter, when there is snow on the ground, in a sleigh, which, from the smooth, gliding, half-flying sensation you experience, is by far the most delightful mode of land gestation (as the learned would call it) I ever experienced.[1]
In 1832 Jonathan Ashbridge and 40 others petitioned the Township of York, asking for a grant of 200 pounds to enable them to turnpike [make a toll road] of the road leading east from the Don Bridge to the Town-line. They were refused.
In 1836 and 1837 workmen straightened the Kingston Road to the alignment that modern-day Queen Street now follows. They “planked” the road surface with three inch thick pine boards, forming a roadway 16 feet wide. This plank road or puncheon ran for 18 miles to the Rouge River. However, the planks were prone to breaking, rot and heaving by frost. It soon decayed into a bone-jarring, kidney-bruising “corduroy” road. Maintaining the road was difficult and expensive and, accordingly, Kingston Road became a toll road to pay for the improvements. Tollgate #Two was at the south west corner of Leslie Street and the Kingston Road.
Shorter streets were often the boundaries of market gardens. These are like rungs on Leslieville’s ladder of streets. Queen Street East, originally Kingston Road, is the base line. The first surveyors used it to project the concessions, sidelines and farm lots. South of Kingston Road along the lake shore lay what was called the “broken front”: that irregular section of land not easily fit into a surveyor’s grid. The broken front west of Carlaw Avenue was used to for grazing cattle. As traffic increased along the Kingston Road, the inn at the corner of Leslie Street and Kingston Road became busier and more important. In the 1850s, Her Majesty’s mail coaches did the Toronto to Kingston trip in 33 hours, either way, stopping at the inns along the way to change horses. From 1856 to 1896, the County of York was responsible for the Kingston Road and contracted the collecting of tolls to private toll-keepers.
Residents soon became unhappy paying for the upkeep of a wooden road, prone to rot and break. Revenues sank and the government took over the major roads leading into York (Dundas Street, Yonge Street and Kingston Road). In 1845, the government sold Kingston Road to a private company controlled by James Beaty. Beaty was a merchant from northern Ireland who claimed to be the flag bearer in Toronto’s first Orange parade. Privatization failed when the railway was opened in 1856. The plank road could not compete. The government resumed responsibility for the three York Roads until York County purchased them. Tolls were collected by the County from 1856 on and the toll system was only abolished completely in 1896.
Kingston Road was renamed Queen Street in 1884 when the City of Toronto annexed Riverside and Leslieville.
[1] Dunlop, 54-55.
Leslieville Historical Society 