Sounds like there's plenty of interesting stuff to seek to keep you entertained along the route. You must have a good few miles on those trainers of yours now? Does Strava enable to log your shoe usage? I seem to recall this being a good feature of Runkeeper back in the day.
Strava lets you log distance for multiple pairs of shoes. Mine had a log of miles before I started using the app. I am due for a new pair. Already chucked one old pair that were falling apart.