Tollgate keepers were a necessary breed around 19th century York Township. Tollgates were not erected to prevent people travelling over private land or to improve the roads in general, but as a means of collecting money for the upkeep of difficult roads like steep hills and fords. Considering all the ravines within today's GTA, there were plenty of places where a toll was established.
I picture a tollkeeper to be a man in his fifties no longer capable of all-day outdoor work, but who could get about enough to get up from his comfortable chair by the fire, go outside, and demand the charge from the teamsters and drovers who moved goods passed his door. I shouldn't generalize on this point--I found one of my great grandfather's sisters working as a tollgate keeper somewhere between Aurora and Bradford in the 1881 census.
But I did expect that tollgate keepers to work in the same place. Even this is now disproved.
From the 1861 census of Yorkville:
William Hughton, tollkeeper, age 61, married, 2 children in household (probably grandchildren);
and from Mitchell's Directory compiled in 1863:
William Heighton, tollgate keeper, Kingston Road, Toronto Liberties
Did old Will find a better paying job or did the occupation run in the family? One thing is for certain: I have just found another surname to recheck!