The best prizes are silly ones that are not expensive. I won a $15 gift certificate that I still remember twenty years later. You know something? The check meant more to me than the cash value and I never even applied it towards a purchase!
I've seen people win a year's supply of rice. The sponsor was a rice company. Trophies are old hat but reward a winner with a teddy bear? It's a winner because a guy just has to give it away.
The funnest races I've seen are costume runs. I was a reindeer in an all-reindeer pageant one Christmas. It was a hoot as we all tried to outdo one another. Then there's the Halloween run where you had to dress as a ghoul. That was a real hoot and could be done any time of the year.
People don't need to earn money through their fun runs. They enjoy the process of running and running with others. It's fun to be out there doing something you enjoy, knowing your entry fee is going to a cause you support. I could see a "Cheese and?" run where each entrant has to represent something that goes with cheese. Look at that pickle running down the road! Look at that gal---she's on a roll. Mr. Mustard just slithered past. Is that a ham down there? (Aren't we all hams when we dress for the occasion?)LOL
Locate a popular cause for step #1. Anything to do with children is always a good one. The indigent elderly are also popular targets for community helpers.
Step #2 is setting up your rewards program. Emphasize fun things, not cash awards.
Step #3 should be the terms of the engagement---make it essential that every entrant wears something peculiar or unusually interesting, or something musical or....gee, there's a zillion possibilities, I'm sure you have good ideas---everybody does.
If you have fun developing your race, the entrants will surely enjoy it.
