Trailguru
No matter how much negative press the App Store is getting at the moment, I’m continually surprised by the availability (and quality) of the software you can get without spending anything at all. Trailguru is a MediaWiki (think software that runs Wikipedia) based site for tracking your running, hiking and snowboarding using GPS.
Sign up for an account on the site, install the application onto the latest generation iPhone (it does work with other devices) and hit “Start”. Location services in the phone grab your position every couple of seconds and record it along with the time you were there. When you’re done, the phone can post the trip directly to the Trailguru site, giving you a map like this. Everything on that page is automatically generated, including the very specific location information in the title.
Of course, it wouldn’t appeal nearly as much to me if there weren’t some nice stats features built in… something a little like my reports page. There’s an argument for not wanting to make this stuff so public, but it doesn’t bother me - getting all this for free means that sharing the data is worth it, in my opinion.