If you're using the City's cycling app to track your routes (or even if you haven't started yet), here's some added incentive:
I asked for this very thing when I reviewed the app. You're welcome.
The contest runs from Oct 6 (yes that was two days ago but I just got the email so get off my back) to Nov 31. So you've got just under two months to amass a contest-worthy number of trips. Then you actually have until Dec 3 to send in your entry.
This is how it works: there are three contest levels for which you can be eligible depending on how many trips you do. The app itself will let you know if you're gold, silver or bronze worthy. You then send in a screen capture of your trips page to the City: email firstname.lastname@example.org, or hashtag #TorontoCyclingApp via Facebook, Twitter or Instagram.
Open up the app now to My Trips (or install it now if you haven't yet). You'll see that gold, silver and bronze match up to 50, 35 and 20 trips. The length of the trip doesn't matter. So that's doable right? Plus there are some nice prizes, including a new bike.
I'm only at 9 trips so I've got to start using this myself.