reason being to help decrease my environmental footprint
Since you mentioned Silk and Earth's Own, I'm going to assume that you're vegetarian or vegan. If not, consider going plant-based as it would reduce your carbon footprint even if you're eating imported food.
That said, it's great that you're buying second-hand!
I'd also suggest keeping an open mind about buying products that are built to last and/or with repairability in mind. That way, even if you have to buy something new, you can keep it out of the landfill for longer.
When I'm looking for Made in Canada products, the ease at which I find them will often depend on what it is. For bike stuff, I've been lucky that we have quite a few companies who make bike bags in the country (Atwater, Arkel, etc.), and even bike trailers (like the Wike company out of Guelph).
Most non-electric items can be found as Made in Canada, and I'll tend to simply do a search during my research of any new products.
The website "Made in CA" (https://madeinca.ca/) would be a good link to bookmark, even though they don't cover EVERY company or product.