Trailrunner (http://www.trailrunnerx.com/), a Mac OS X solution for folks doing long distance sports, has been updated to version 3.1. You can now send Trails to the iPhone and iPad versions of the app.
With TrailRunner you can plan workout routes on a geographical map, export the route directions as small NanoMaps onto an iPod and import workout data from the Nike + iPod sports kit back into the workout diary. Other features are an exercise plan, .Mac weblog publishing, a GPS, GPX and KML import/export, an integrated map and elevation data download from global mapping services like USGS topo maps.
TrailRunner is donationware. You can download the software, and, if you like it, make a donation to the developer.