I'm asked fairly often what I do to stay current in the Ruby/Rails/Software Development communities. Previously, I published a list of the blogs I read, but manually posting that list now and then isn't really a long term solution.
So, to solve the issue I created whatdoiread.com. You can subscribe to the Ruby feed or the Software Development feed (or both) and you'll be reading the same blog posts that I read.
Other than blogs I also really like the audio and video content that's becoming more popular. In particular I try to stay up to date on the Rails Envy Podcast and Peepcode Screencasts.
Of course, I read books also, mostly Pragmatic Programmer titles these days, but I've also enjoyed the AW Professional Ruby Series. Generally I stick to titles that have been recommended by a few people I trust.
I also find conferences to be great places to meet the people who are shaping the industry. Some of the most enlightening conversations of my career have been over drinks when the sessions have ended.
Lastly, working for ThoughtWorks is the best possible career decision I could have made. The internal mailing lists and the people I work with on a daily basis constantly challenge and educate me.