It really would depend on:

• Where you were coming from in Simcoe County.
• What season you were travelling in.

For example, if you were coming from a city such as Barrie you would most likely be on a public stagecoach or private coach (or perhaps a sled in the winter) as Barrie didn't have a railroad connection until 1865. They would travel from Simcoe County to Toronto, which would be the main hub basically. They would then hop on another stagecoach to head east to Kingston as, like Barrie, there was no railway connections in Toronto until 1853. I'd say it would be a long and uncomfortable ride! One might also take a private boat down Lake Ontario to Kingston from Toronto, if you could afford it. But I'd say the stagecoach was more typical.

I hope this helps!

Oh man, I get to bust out some Ontario trivia! So, fastest way from Simcoe county is down Lake Simcoe to Holland Landing, then down Yonge Street to Toronto. From Toronto you're probably going to take a boat down Lake Ontario to Kingston.

For added trivia, Lake Simcoe was renamed that by John Graves Simcoe (for his father). Before that is was generally known as Lake Toronto. The Toronto Passage was a shortcut from Lake Ontario to Lake Huron. It started at York (Toronto), ran up the Humber River then up Lake Simcoe into Lake Couchiching, then down the Severn River into Georgian Bay.

I'm drawing this from The History of the County of Ontario 1615-1875