[pugworthy]

I use Strava to track walks, then import the data into the CityStrides website. They work well together.

Route planning is tough, even with automated helpers like Every Street Challenge (http://www.everystreetchallenge.com/). Automated ones don't take into account things like being able to cut through a park as a short cut.

Usually for route planning I pick a chunk of streets bound north and south, east and west by some primary streets, then print it out and hand-optimize the route.