By Kent Huffman
Every fall, the Center for the Arts in the Bowery in Winnsboro, Texas becomes the focal point throughout Texas and the Southwest United States for celebrating and honoring cowboy culture. Officially titled the “Winnsboro Cowboy Music & Poetry Gathering,” this special event attracts cowboy cultural enthusiasts from all around who appreciate that genre of music, as well as other art forms centering around the cowboy lifestyle.
This two-day celebration features not only cowboy music, poetry, and art on Market Street, but also some special events, such as square dancing, mule wagon rides, and a calf-roping challenge. There are also several activities for children, including face painting and kid’s crafts.
On Walnut and Elm Streets, you can find an authentic chuckwagon serving cowboy beans, cornbread, and cobbler; a drover tent with drover characters; several games, including cornhole and horseshoes; cornhusk doll making, a photoshoot with “Whiskey,” the horse; a visit with “T-Bone Tom,” the longhorn steer and “Bucky,” the mini bucking bull; and even baby goat petting!
Dom Flemons and Andy Hedges Took the Lead
This year’s event featured cowboy culture conversations with Dom Flemons and Andy Hedges, who discussed the history of black cowboys and their role in the tradition of cowboy music and poetry.
According to his bio, Dom Flemons “is known as ‘The American Songster,’ since his repertoire covers more than 100 years of American roots music. Flemons is a folk musician, black country artist, songwriter, multi-instrumentalist, music scholar, historian, actor, slam poet, record collector, curator, podcaster, cultural commentator, influencer, and the creator, host, and producer of the American Songster Radio Show on WSM in Nashville, Tennessee.”
“Flemons is the co-founder and original member of the groundbreaking Carolina Chocolate Drops, the first-ever black string band to win a Grammy Award. Over the past 25 years, Flemons has received major awards, gained world-wide media recognition, and he has become one of the most influential and highly decorated voices in American roots music.”
Andy Hedges is a “songster, reciter, storyteller, guitarist, and collector of cowboy songs and poems. The son of an Italian schoolteacher and a rodeo cowboy turned preacher, Hedges was born in Lubbock, Texas in the spring of 1980. He grew up in the small community of Tokio, Texas, where his family paid rent on an old farmhouse by looking after a few head of cattle. It was there that Hedges fell in love with traditional music by listening to his father’s cassettes of cowboy songs. His vast and varied repertoire includes classic cowboy poetry recitations, obscure cowboy songs, dust bowl ballads, and blues.”
“Hedges also hosts a podcast, ‘Cowboy Crossroads,’ which features in-depth interviews with fellow musicians and poets. He has performed many times with folk legend Ramblin’ Jack Elliott, and the duo’s performance at the 60th Newport Folk Festival was named one of the ‘10 Best Things We Saw’ by Rolling Stone. In 2023, Hedges made his debut at the Grand Ole Opry in Nashville, Tennessee, and in 2024, he brought his album, ‘Roll On, Cowboys’ to Carnegie Hall in New York City.”
Cowboys and Cowgirls Kept Everyone Entertained
Kristyn Harris, along with Miss Devon and the Outlaw, entertained the crowd with an afternoon of cowboy and western swing music. That evening, Kristyn was joined by Mike Blakely and Andy Wilkinson for a “Three Texans” concert.
The next day, Joel Nelson and Andy Hedges—dedicated writers, performers, historians, and documentarians—presented an oral history of the American cowboy. That afternoon also featured poetry by Jay Snider, the current poet laureate of Oklahoma and a past bull riding champion; Teresa Burleson, director of the Stockyards Museum at the historic Fort Worth Stockyards; and Joel Nelson, owner of a 24,000-acre ranch and the winner of the 2020 Working Cowboy Award.
The final session featured some fascinating stories, poetry, and songs from Andy Hedges from his show, “Roll On, Cowboys.” He played a sold-out feature at Carnegie Hall in New York City this past spring! Hedges was joined on the Bowery stage by Dom Flemons and Pipp Gillette, both of whom were performers from Hedges’ Carnegie Hall production.

But Wait—There’s More!
Not to be outdone by all the amazing poetry and songs at the Winnsboro Cowboy Poetry & Music Gathering, a number of talented artists submitted their paintings and other artistic creations that celebrate the cowboy lifestyle for a state-wide juried art exhibition and awards presentation. The exhibit will be open at the Winnsboro Center for the Arts through November 23.
Be sure to put next fall’s Cowboy Poetry & Music Gathering on your calendar right now. We will expect to see you “ride up” then for all the great music, stories, poetry, and art this annual event offers. And consider joining the Winnsboro Center for the Arts to have access to all the other great events and opportunities it provides to East Texas and beyond!

