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 - An Old-Time Tractor Demonstration - by Kim Pratt. Sam was born in rural Kansas in 1926. His dad was a hard-working farmer and the children worked hard everyday to help ends meet. In the rural area he grew up in, the highlight of the week was Saturday when many people took a break from their work to go to town. It was on one such Saturday in the early 1940's when Sam was 16 years old that he ended up in Dennison, Kansas to watch a demonstration of a new tractor being put on by a local dealer. It was an Allis-Chalmers tractor dealership,
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