Howdy Joe, I know something about Cowboy Poetry being involved with various gatherings. The greatest single reference was created by Margo Metegrano as the Center for Western and Cowboy Poetry Inc. better known as CowboyPoetry.com. It contained the classic as well as current Cowboy Poetry and information on cowboy gatherings around the country. Alas, even the mountains do not last forever but thankfully this great source has been archived. And recently someone has made some improvements to make all the material more accessible. So you will find much of what you are looking for in the link below.

The Center for Western and Cowboy Poetry Inc. (archived)

There is a new ray of hope in Cowboy Poetry News. They list gatherings taking place around the U.S. and are working to be a link between them. The link is below.

Cowboy Poetry News

I must not neglect to add that the gathering that everyone first thinks of is at Elko. They have been running for a good while and you'll find some good material and resources on their website. It is linked below.

National Cowboy Poetry Gathering

So check out the above. I focus on the classic poets, those of the end of the 19th century and early 20th. I can help direct you to those and contemporary cowboy poets. Start with Badger Clark.