Other than when I'm riding between states and have a definite date that I need to arrive, I rarely plan my rides. Sometimes I'll let the wind tell me which way to go (it is possible to do a loop with all tail winds, if you have the right geography). Sometimes I just head out and explore some road that I've never ridden on before.

Oddly, the last time I troubled myself to plan a ride was last year. My wife and I were riding in our favorite area (known as the O&C lands) and we actually plotted out a ride on ridewithgps and brought a tablet with us that has a gps. We dutifully followed the gravel road that was indicated right to where it ceased to exist. After a nice chuckle, we rode back up to the ridge and explored a different logging road that took us to a familiar road. That ride has since become a favorite of ours that we nicknamed Sugar because it involves riding on the C-line and turning onto the H-line (C&H Sugar).