 This road would serve as the initial mail road linking Kingston to Toronto , but was poorly maintained and soon allowed to fall into disrepair . By 1817 , the Kingston Road replaced or bypass much of Danforth 's Road , following a similar path to the Trent River ( with minor improvements in routing around Scarborough , Port Hope , Cobourg and Grafton ) but then blazing a more northerly route through Belleville and Napanee . Like the Danforth Road before it , this 1817 York Road was initially a muddy dirt road ; it would , however , suffice to establish reliable scheduled stagecoach runs by which mail and passengers could make the two @-@ day trip from Kingston to Toronto and permit enterprises ( such as the branches of the newly established Bank of Montreal ) safe and timely delivery of documents and valuables . By 1839 , the Napanee @-@ Kingston route was being improved for use as a gravel toll road . 
