 East of Highway 400, the highway entered the urban area of Bradford, where it ended at an intersection with former Highway 11, which travelled north along Yonge Street/Barrie Street as well as east along Bridge Street.Highway 88 was built in the 1850s and was the first plank road built in Simcoe County, which originally connected Holland Landing with Bond Head.The road was about 1 inch thick and was wide enough for a wagon.