Create custom running routes and GPS running log files

I will specify area and what the running route needs to spell out. In some cases, I may specify where the route needs to pass. For example: running route that says "TEST" in Chicago and passes by Building A. You provide a file (GPX, FIT, TCX, or something else) I can upload to Strava/Mapmyrun/Tomtom File needs to make sense. (running speed/etc.) Alternatively, you provide a howto so that I can do this myself. Example of what I mean attached.