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Strava have released a new premium feature to automatically plan routes based on a couple of parameters.
DC Rainmaker, as usual, provides an excellent introduction:
However, I tried creating a couple of "dirt" routes on my area (North Vancouver, BC) and even with the fairly dense network of mountain bike trails we had, Strava was routing me up serious mountaineering routes, into prohibited areas (watersheds) and down a stupidly steep uphill only hiking trail (the Grouse Grind).
I'm sure there will be more comedy gold until they figure out their algorithm.

Try it and post your results here!