Class Diagrams maya at time be over rated, but I find them useful to look at when first coming onto a project inorder to get a birds eye view. This is how to generate a class diagram for a Rails 3.x project on ruby 1.9.x.
Install graphviz, railroady uses it to generate the diagrams.
$ brew update && brew install graphviz
Add roadroady to your gem file. (Railroady is a follow-on to the orginal railroad gem. It works well with Rails 3.x and ruby 1.9.2. I could not get the railroad gem to work at all.)
gem "railroady"
Note: Make sure doc directory exists. For me the next step fails if it's missing.
Run rake tasks to generate diagrams and place them in the doc directory.
$ rake diagram:all