Gaines published New Tradition: Western Verse in 1990 and has been on the trail story telling ever since. In that year he became the Texas State representative Poet at the National Cowboy Poetry Gathering in Elko, Nevada, returning in 1991 and 1992. Since that time he has performed at a number of events such as the National Cowboy Symposium, National Cowboy Hall of Fame, Western Heritage Classic, Red Stegall’s Cowboy Gathering. Gaines has also worked at a number of festivals, including the Texas Folklife Festival.

Dennis Gaines has been featured on the "Texas Country Reporter" television show, in a segment that generated one of the highest viewer response rates in the show’s history. He has also been featured in "Americana Digest" and in Southern Living magazine.