Winnsboro Center for the Arts (WCA) presents the 2025 Winnsboro Cowboy Music and Poetry Gathering on Friday and Saturday, September 26 and 27 with concerts and presentations by top entertainers, free Western fun activities for the whole family, and a juried cowboy-themed art exhibition. The event takes place in multiple downtown locations combining cowboy culture and artistry, and drawing the finest cowboy poets, storytellers, and musicians from Texas and beyond.
This year’s lineup includes the best-of-the-best in the cowboy music and poetry industry. Friday kicks off at 1 p.m. with Cowboy Culture Conversations featuring Pipp Gillette, a Texas rancher, cowboy musician and winner of several Western Heritage Awards, in conversation with Andy Hedges, who has performed his cowboy music at both the Grand Ole Opry and Carnegie Hall. In this conversation, Hedges, who grew up tending cattle in small-town Texas, talks with Gillette about merging his music and love of the cowboy lifestyle with working the family ranch near Lovelady, Texas, land that in Gillette’s family since 1912.
Cowboy Poetry and Cowboy Songs with Jay Snider, Teresa Burleson, and Bob Campbell is at 4 p.m. Friday. Snider is currently serving his second year as the Poet Laureate of Oklahoma and is a past bull riding champion, which brings an authentic cowboy experience to his poetry. Burleson is a two-time International Western Music Association (IWMA) Female Poet of the Year and serves as director of the Stockyards Museum at the historic Fort Worth Stockyards. Campbell is an award-winning songwriter, renowned for his performances of traditional cowboy and folk ballads from Texas and the American West.
Some of the ticketed entertainers of the Winnsboro Cowboy Music & Poetry Gathering are Andy Hedges, Kristyn Harris, Jay Snider, Joel Nelson, and Teresa Burleson.
Vendors are set up in the Bowery Pedestrian Park from noon to 8 p.m. on Friday and 10 a.m. to 3 p.m. on Saturday.
An Evening of Song & Chili takes place from 5 to 8 p.m. on Friday. All-you-can-eat chili tickets are $10 for adults/teens and $5 for children 12 and under.
The Friday Evening Cowboy Concert starts at 7:30 p.m. with three award-winning performers. Pipp Gillette returns to The Bowery Stage along with Kristyn Harris and Andy Wilkinson. Harris is the current (and seven-time winner) of the IWMA Female Performer of the Year and five-time Entertainer of the Year. Wilkinson is a poet, playwright, teacher, writer and singer of Western folk music from Lubbock, Texas.
Activities in the Bowery Pedestrian Park and a pop up Cowboy Camp on Saturday include a chuck wagon with cowboy fixings such as cornbread, beans, and cobbler; mule wagon rides; a Los Diablos Tejanos (Texas Rangers) reenactment village; music and poetry performances by regional artists; cornhusk doll-making; face painting; chainsaw carvings, photoshoot with Whiskey the Horse, a Western-themed mini golf course; Smarty the Cow Roping Dummy; and a baby goat petting zoo.
“Ancient Wisdom” by Shirley Gordon was a first place winner in the 2024 Cowboy art exhibition. This year’s Cowboy Tales exhibition of Western art is from September 24 through November 15.
One of the highlights of the festival is Cowboy Tales, a free art exhibition at WCA from September 24 through November 15 that illustrates the theme of Western culture and imagery.
Another Western-themed art exhibition is featured at the Bowery Boutique & Gallery. Works by Sharon Cromer are there from September 26 to October 25.
“The Crossing” by Sharon Cromer is featured in the Bowery Boutique & Gallery in a Western exhibition of her work from September 26 to October 25.
Saturday’s ticketed events began at 1 p.m. with Cowboy Culture Conversations bringing Andy Wilkinson back to the stage to discuss legendary American West rancher Charlie Goodnight and historical songwriting with Andy Hedges. Wilkinson, an award-winning writer and performer, is also a historian who served as Artist-in-Residence at Texas Tech University’s Southwest Collection. Hedges, a student of cowboy history and lore, is considered one of the most recognized cowboy performers today and one of the most prominent leaders of Western music. Together, both Andys embody the spirit of the American West, where music, poetry and history are woven into a timeless and ever-evolving story.
The Kristyn Harris Trio performs Western swing music at 4 p.m. The group features Kristyn Harris, a favorite of the annual Cowboy Music and Poetry Gatherings. Her past performances featured dynamic collaborations with fiddler Hailey Sandoz. This year, Harris brings even more energy to The Bowery Stage by adding Matthew Walton to the mix. Walton is a master of pedal steel, lap steel, bass, acoustic and electric guitar. Together, this trio promises a high-energy set brimming with the authentic western spirit our cowboy music audiences love.
Saturday evenings Carnegie Cowboys Concert starts at 7:30 p.m. bringing Carnegie Hall to Winnsboro. Rod Taylor (of “The Rifters” fame) was one of 11 cowboy singers who joined Andy Hedges in his 2024 “Roll on, Cowboys” show at Carnegie Hall. This year marks Taylor’s first appearance at the Winnsboro gathering. Renowned poet/Grammy-nominated performer/rancher Joel Nelson joins Taylor and Hedges to close out the 2025 gathering. This spectacular performance showcases some of the very finest in cowboy music and poetry.
Unless otherwise noted, activities on and around the Bowery Pedestrian Park are free. Concert and presentation tickets range from $20 to $80 with discounted day passes available. Get tickets on the WCA website.
