Most of the big entertainers (the ones that frequent the radio air waves) are booked for fairs and festivals in the early part of December in Las Vegas. There is a big convention out there where the agents meet with fairs and festivals across the country to book acts. Most of them are 6 figure a night acts.
As far as your local county fair, some states have an annual convention where fairs and festivals have access to talent agents, carnivals, sound companies, motorsports promoters, etc. This is where many of them book what is coming to your local fair. My dad has a sound company and has been a member in the Iowa fair association for many years. I know Iowa, Nebraska, Minnesota & wisconsin hold these type of conventions annually.
Other option is try the website of the band your thinking about and you might be able to make contact for booking them through there.
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Today's Featured Article - New Life for an Old Allis - by Tyler Woods. My friend Jon, has an old '39 Allis Chalmers B. He thought it a marginal tractor that had long since served its time. She smoked terribly and never had much power but he couldn't afford another so he was limping along with what he had. Jon's Allis has a small front loader and though it doesn't carry much, it serves his needs. It was the hard starting and low power that made him think it was time to replace the old girl. Jon called me to help him discover why his tractor wouldn't start
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