The national organization for rail trails in Canada is The Trans Canada Trail, while in the USA it is The Rails-to-Trails Conservancy.
The Ontario Trails Council is a non-profit organization dedicated to the creation of new trails, and they may be able to help if you want to promote the development of trails in your community.
Cycle touring companies that operate in Ontario include Bike ON Tours.
Some sites promoting cycling in Ontario:
A site promoting trails in USA is American Trails.
Where to Stay for Caledon Trailway and Elora - Cataract Trailway
I don't normally recommend accommodations but I am going to make an exception. I stayed in a very nice B&B near Belfountain and it is convenient to both the Caledon and Elora - Cataract Trails:
Heatherlea Highlands Bed & Breakfast
I am not getting compensation for this plug