I am a member of the Wisconsin Track Club and we're hosting a one mile road race in downtown Madison. Here's the website for more info (or feel free to post a question to me on here).
We recently decided to add prize money to the event; it hasn't been posted on the website yet, on flyers, etc. There will be $100, $50, and $25 for 1st-3rd for males and females.
There is also a competition for schools, where whichever school has the most participants, we donate $500 to their track program ($250 for second).
There is a slight incline on part of the square, but its a decently fast course that goes around the capitol 1.75 times.
Course records:
Men: 4:00.07 - Rod Dehaven (1994);
Women: 4:38.75 - Sarah Thorsett (1994)
& Jenelle Deatherage (2003)