Generic, perhaps useless advice, get an ebike if possible so you can use detours, stop-and-go, without getting slowed down to a crawl.
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An e-bike would 100% make this type of trip a lot easier, and faster. But I'm working my way up to a 230+km ride later in the summer, so any long-distance training is going to help.
99% of my problem right now is simply because I don't know any of the infrastructure west of Pickering and north of the Waterfront trail in Toronto.
I've put several hours into route planning already, and Finch seems to be the best so far. This gives me the opportunity to ride the Finch hydro corridor for a fair bit.
So far, I'm up to 78.7km one way, up from around 74km being the fastest route suggested by the auto-routing sites. Not too bad, but avoids some 80km roads.
Wow, now that's a goal!
It is. I'd like to go further, but I have to be home in time to make dinner. 😂😒
Last Canada Day, I rode to the city for the first time and got to explore Tommy Thompson Park before reaching the Toronto Music Garden. That was 182 km, and such an enjoyable day!
Check out https://www.cyclosm.org/ which clearly displays bike infrastructure to help you find the safest route.
I contribute to OSM, so I'm well aware of cycleOSM and make use of it and the cycle map layers.
But “cycling infrastructure” is often complex and nuanced around here.
For example, some high speed roads have multi-use paths on certain sections. Knowing when/where/how to merge into them is typically down to experience of the area.
And some areas that I've already mapped out require me to use the sidewalk for a short while in order to get to the trail links (because you can't get to them directly from the road).
This sort of hit-and-miss aspect is likely going to be the biggest challenge, second to headwind. LOL
That said, I think I've planned out my route, and will do a final comb over with the help of Google street view to visualize what I can expect. Of course, if I just stuck to Taunton/Steeles, it'd be "easier" to plan, but not nearly as safe to ride with speed limits of 80km/h (plus 20 to 40km/h over because sPeEd LiMiTs ArE fOr LoSeRs!).
I may, at some point, try Taunton/Steels from Pickering to Markham, just to see how it is, but not for this ride.
Edit: minor correction for clarity.