We used to have a calendar in our sidebar. Powered by upcoming.org, it kinda sucked, largely because there was no quality control; instead, it merely listed every event that Yahoo! did. We got rid of it about a year ago, and ever since we've been quite happy without it. Lately, though, as the amount of content we have and the number of people reading us has been increasing, we've noticed that it's been getting a bit harder for people to find event listings on us, especially at a glance.
So, with that in mind, we've added a "What's On" box to our left-hand column. In it, we'll include the dates, times, and locations of events—but only those that we write about on Torontoist. We're still experimenting with it, so it's very far from perfect yet, but let us know in the comments for this article if you have any suggestions on how to improve it (both aesthetically and content-wise).
Also, some substantially bigger changes will be coming to Torontoist soon with respect to comments and navigation. Stay tuned for those. (And, of course, we're hiring right now, too.)
Photo by AttilaSoylu from the Torontoist Flickr Pool.

Elsewhere in the Ist-a-Verse
I suppose the first question is: for the sake of de-cluttering, should we ditch the locations?
i vote for leaving the location on the listings. but may i suggest maybe de-cluttering the look by just adding a space between each item? it's a little bit confusing to read with all the dates and events running into each other...
as well, how about adding one-word tags after each date, so that readers can quickly scan the list for particular type of events: arts, music, festivals, food, etc.
I'm actually in the midst of putting in a spacer image right now and messing with the size to get it just right. As for one-word tags -- great idea, but wouldn't that add to the clutter?
the tags and the clutter... i think tags would be ok, if they're maybe in a different colour? or bolded?
Any chance of getting either an RSS or ical feed? Perhaps setting up a public Google Calender?
It's a possibility, Marcus, but I think that RSS is more likely than a public calendar (since we're not really listing THAT many things; upcoming.org's list of events is probably a better bet for completists, as they have an RSS feed, iCal, and Yahoo compatibility).
However, if there are any super-smart people who want to help with coding/iCal/RSS (something I'm not amazing at), I'm not gonna stop 'em from lending a hand.
Here's how I have it set up to work for now. The listings are simply pulled into the column from a separate php file. Although there's surely a better way to make it work, I'm doing all the work manually (adding event by event) for now.
Also, it's probably worth mentioning that our sidebar content is going to be cut in half soon and slightly re-organized. The goal is to make information easily-accessible, while also reducing clutter as much as possible. We've come a long way.
David: Can we chat? Check my Facebook for my cell#.
Hey there. I'm a developer on Upcoming.
For what it's worth, there are ways to filter the listings. You could get an account on Upcoming, and then tag some events as 'torontoist'. Then publish an RSS widget here based on that tag.
A group "Deaf UK events" does just this: http://upcoming.yahoo.com/tag/deafukevents
Check out the "Subscribe" widget at the top right -- there are RSS, iCal and other syndication formats. We have a default RSS widget that you can style up to suit Torontoist as well.
Anyway, sorry that it didn't work out for you the first time, but I'd be happy to help if this sounds like a good option.
Thanks very much, Neil; I've sent you a private e-mail about this. We obviously like upcoming.org, it just didn't really suit our needs.
For everyone else (whoever's reading this, I suppose), I feel as if it's still too cluttered as-is. What do people think of ditching everything but date/event name? So saying goodbye to times + locations.
Also, re: colour-coding, I'm working on figuring out an elegant way to do it. I might do a legend; little boxes of different colours to denote each kind of event (green for environment, etc.)