What are your interests? Would you like to be notified of events in your city that matches your interests?
Eventful.com has a TON of events. And you can create custom calendars based on a keyword. You can create custom calendars based on a set of keywords. It will notify you via email when there are new events.
AND! You could easily add it to your calendar via the iCal feed.
I made a bunch of watch calendars for Chicago with the following keywords: Antarctica, atari, badminton, dodgeball, Estonia, free hugs, hot wheels, laser tag, monster jam, Nerf, origami, paper airplanes, pinball, pinewood derby, Podcast, rock paper scissors, snowball, SpongeBob, wiffleball, WWE, and YouTube. Check ’em out at: http://eventful.com/calendars?q=owner:spudart.