Cycling Outside Waterloo Region

[clasher]

I think you're probably thinking of the Caledon Trailway. A friend and I actually rode from Kitchener to Orillia almost entirely on rail trail using the Elora-Cataract Trail, the Caledon Trailway, and the Oro-Medonte Rail Trail.

The amazing thing is that you could actually bike from Goderich to Midland using rail trail almost the whole way except for a few small gaps.
https://ridewithgps.com/routes/28203736

Yup it's the Caledon trail I'm thinking of... I usually do the climb up Mississauga road instead of using the trail. I don't mind the rail trails but generally prefer riding secondary and gravel roads nowadays, but any rail trail that has bridges on it will pique my interest. I've ridden from Barrie to Orillia a few times but never taken that trail either, the road that runs along it is quiet enough riding for my tastes.

It's the gaps that worry me when planning such a trip. I worry I will get there, and I will be faced with riding up a freeway with no shoulder, or turning around and going home.

Sadly, the best way I've found to figure out how the options are is to go through it section by section on streetview, which is no guarantee of accuracy.

A bit of research isn't really that bad of a thing to do, I use streetview and satellite when I plan a driving trip too.

Another rough trail worth avoiding is the one that goes from Port Elgin to Walkerton, it's doable on a cross bike but better on an MTB since it's mostly a trail used by ATVs and dirtbikes.