Another possibility, if you don't want to play with scripts is to use a web-based calendar service like CalendarHub, 30Boxes, Upcoming.org or Calendars.net. Depending on which you pick, you can drop the web-based version into an iframe in the layout area.
If you use an iCal-supported desktop calendar, it's even easier. I'm a Mac user, so I just use my normal calendar software Apple's iCal. I create a subcalendar of recommended bands playing in the Toronto area. When I update that, the changes are automatically reflected at my web site...
You can arrange for multiple updaters as long as they also have iCal-compatible dektop software. I forget how you set the permissions, because I don't use that feature yet, and it probably depends on which calendar software you use on your desktop. I don't know if Outlook is iCal enabled, but you might check.