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I have tried one site called Alltrails.com You can download many routes to get an idea of the total area. And draw maps by and that follow trails and roads automatically. I think Ride with GPS and strava could work similarly. It gets clunky doing it all at once but alltrails has a pretty good free option and you can split up into smaller files once you get things set. I’m sure you could buy some mapping software for more bang but why…