Danforth Ave/Danforth Rd/Kingston Rd (Hwy 2)

Kingston Road, 1830

The ride out from Toronto passes along all three of the above roads, which have an interconnected history.  

 The first connecting road between York and Kingston (Catarqui) was laid out by Asa Danforth Jr., starting in 1799, an American entrepreneur (some might say carpetbagger). He took major financial risks signing contracts with the British governors to deliver several early roads. He was paid $90.00/mile, completing 106 miles in just over a year. The contract(s) completion was disputed by the British, nearly bankrupting Danforth. His trail, which followed indigenous routes in places, proved to be poorly located and unpopular with settlers. On Day 1 we ride along it as Lakeshore Road between Newcastle and Port Hope. Danforth’s road was used for military purposes during the War of 1812. It was replaced further north with a straighter Kingston Road (HWY 2) in 1817. The Kingston Road was on the same alignment in several sections as Danforth’s road. Much of our route on Days 1, 2, and 3 follow either Danforth’s road, or the later 1817 Kingston Road.  

 Just to totally confuse you, Danforth Avenue is NOT part of the 1799 road, nor the Kingston Road (1817). Danforth Avenue was named after Asa Danforth, because it was one of the roads he had planned but never executed. Danforth Avenue was built circa 1850.  



Architectural Conservancy Ontario

ACO is pleased to be partnering with PWA’s Friends for Life Bike Rally to bring alive some of the beautiful heritage along the route.  To learn more about ACO and our activities across Ontario, or to become a member, check out

Architectural Conservancy Ontario (ACO) has been working since 1933 to preserve Ontario’s architecturally significant structures – not just those of the 18th and 19th centuries, but more modern ones as well – saving them for future generations.  

ACO’s mission is “through education and advocacy, to encourage the conservation and re-use of structures, districts and landscapes of architectural, historic and cultural significance, to inspire and benefit Ontarians.” Volunteers in our 25 branches across Ontario are working to celebrate the heritage in the communities.