I'm still slightly new to editing OSM as a MTBer, maxerickson and c0nsumer have covered the details of how to do this already very well, but i found after comparing a seemingly never ending number of competing apps in this space, i found Viewranger GPS really useful:
a) For planning routes in advance to then download to your smartphone and follow using the app (as mentioned elsewhere OSM was definitely the best mapping layer to use for this both as a resource and as a mechanism to feed your own updates back in).
b) For creating tracks from the routes you've actually cycled which can then be uploaded to the website for later examination.
c) In addition to b) you can annotate your uploaded track on the website with actual pictures from the journey round. These can be from a number of sources (i use flickr) and it will either time sync or gps sync them to the route so you get a nice one stop for looking at previous trips. This has the added benefit you can just take pictures as your going round to then refer back to when fixing OSM without having to worry about making notes as to where it was etc.
Has anyone else used this app or anything else to do this as i'd be interested if there's any alternative ways.
Example annotated track from Hay Bluff:
http://my.viewranger.com/track/details/MTIzMzAxNg==