For my entire career, I’ve lived and worked in York Region. Sure, it’s not the easiest place to get around by bike or transit but I’ve made it work. I’ve come to know several decent bicycle routes and have built up a familiarity with the potholes, bad sewer grates and the flow of traffic during rush hour.
This is all to change. My York Region office is closing down in an effort to manage overhead costs, and the employees will be distributed to other GTA offices. It looks like I’ve drawn downtown Toronto. This isn’t all bad, as a) I’ve still got a job, and b) there are more transit choices available.
From a bikey perspective, this means that I’ll probably be riding a lot less. Some 80-90% of my time on the bike is commuting. I may be able to ride to a GO station (2.5 km, seems hardly worth it!) or a subway stop (~14 km). The latter is about the length of my current commute, all in and then I would need to add another 30-40 min on top of that. I’m not sure I can find that kind of time. I guess it’s good to have options!
To give you proper advice on a bike commute from York Region downtown I’d have to know where in the huge area you are, or at least the closest Go station. Instead I will tell you what I did for a year. I had a friend with the same commute, to whom I happily paid money to car-pool. Several times a week, when she had other evening commitments, I would load my bike in the back of her car for the morning ride, and ride it 45km home, from the north end of Brampton to Toronto’s ‘Little Italy’. I was lucky to have a good bike, an understanding friend, and some good lights.
With the GO train so convenient to you, you could make it work if you can take the train outside of rush-hour (which is hard), or have a gym to shower at if you ride there in the mornings. Guessing your ride at 30-50km, in your shoes I might get a good folding bike: take it on the train during rush hour, ride home. Failing that, ride in/ride home on alternate days, or do both directions in one day, with rest days between. All I know is that I need my commute ride for exercise, as it’s hard to get time and motivation for it at other times.
Good luck!
Just noticed Richmond Hill in another post, so that answers something. No off-peak Go service. However, you can use parts of the Don Valley trails.