This season will be our third or fourth year at some of the festivals where we vend. We will vend at smaller festivals if the application fee isn't over the top. For example, there is a Strawberry festival just down the street from us that wants $1,650 for a spot and the crowds are not that big. People think we are crazy for not vending in our own backyard, but we tried it there one year and lost a lot of money. We pay $2,500 to vend at the Red Bull GP at Laguna Seca raceway, but we make a lot of money because of the massive crowds. At that event lines are 40 people deep during the middle of the day. We now even sell tri-tip breakfast burritos because we see people looking for food even before the gates open.
Some events the organizers ask us before we leave for the weekend if we'll come back next year. I think that is because we try to work with the organizers instead of being whiners. I can't tell you how many times I have seen vendors scream and yell at the organizers instead of trying to work through their issues. The organizers often say those people will not be asked back. It never pays to be a primadonna.
The biggest festival in our area, The Gilroy Garlic Festival, we have been on the waiting list for 3 years. It's almost impossible to get in there!
Ask a lot of questions of the organizers. Try to get the name of some of their regular vendors and talk to them, if you are able. When you are at an event talk to the other vendors and ask about their experiences and where are their favorite place to vend, etc.