No one got to where they are all on their own. Several resources have inspired us and directed us to amazing places.
Ron and Ryan have done a great job finding and linking amazing routes. Largely in the Columbia Gorge and Mt. Hood area. Their focus is more gravel to back country mountain biking. They also still have some old Velodirt routes too, which was a group that was ahead of it’s time making some classic routes that have become well known.
David has taken a page from OMTM and made a truly fantastic resources for The Dalles area.
We don’t know Jay but he has been all over the dang place. Lots of great resources that is more California-focused. He is not afraid of an out-n-back.
Back in the day before GPS routes were on your head unit we had books. River City Bicycles helped put out two volumes with great Portland region bike routes. Eventually they moved this to the new fangled Internet and this great resources is your to explore, FREE.
This is a deep cut if you want to explore Oregon’s Southern Coast. It’s a book written by Coos Bay local Tom Baake, it’s cheap and a quite thorough resource.
This site has become quintessential to route making and they are based in Portland. It used to be pretty free but like all good digital things eventually you have to pay for it. But it’s tools are great. Would recommend. Their latest release has heatmaps and surface types.
Strava is ubiquitous to sharing your rides. But their heatmaps are great to get an idea of where you can ride. They frankly just have more data than RWGPS so checking their heatmap is a good exercise.