2025 Winnsboro Cowboy Music and Poetry Gathering

Start: Friday, September 26, 2025 1:00PM
End: Saturday, September 27, 2025 9:30PM

Songs, Stories and the Spirit of the West Ride into Winnsboro for the 2025 Cowboy Music and Poetry Gathering

Cowboy Culture comes to life again in historic Downtown Winnsboro

Winnsboro Center for the Arts (WCA) is excited to announce the 2025 Winnsboro Cowboy Music and Poetry Gathering on Friday and Saturday, September 26 and 27. The event combines cowboy culture and artistry, and draws the finest cowboy poets, storytellers and musicians from Texas and beyond. The gathering takes place on The Bowery in Downtown Winnsboro. Tickets are on sale now.

“Our lineup of professional artists showcases the finest storytellers, those who turn the hard work of cowboys and ranchers into timeless art. Their words honor cowboy heritage with both heart and harmony,” said Mary White, WCA board president and acting executive director.

This year’s lineup includes these very best-of-the-best in the cowboy music and poetry industry:

Friday, September 26:                                                                                                                                             

1 p.m.: “Cowboy Culture Conversations” features Pipp Gillette, 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, will talk with Gillette about merging his music and love of the cowboy lifestyle with working the family ranch near Lovelady, Texas, land that has been in Gillette’s family since 1912.

4 p.m.: “Cowboy Poetry and Cowboy Songs” features Jay Snider, Teresa Burleson and Bob Campbell. 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.

7:30 p.m.: “Evening Cowboy Concert” is a tribute to cowboy music from three award-winning performers. Pipp Gillette returns to The Bowery stage along with Kristyn Harris and Andy Wilkinson. Harris, from Burleson, Texas, 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.

Saturday, September 27:

1 p.m.: “Cowboy Culture Conversations” brings 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 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.

4 p.m.: “Kristyn Harris Trio - Western Swing Music” features Kristyn Harris, a favorite of our annual Cowboy Music and Poetry Gatherings. Her past performances, all unforgettable shows, have featured dynamic collaborations with fiddler Hailey Sandoz. This year, Kristyn is bringing 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.

7:30 p.m.: “Carnegie Cowboys Concert” brings 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 will join Rod and Andy to close out the 2025 gathering. This spectacular performance will showcase some of the very finest in cowboy music and poetry.

In addition to the weekend performances, there will be two days of fun, FREE activities for the whole family. Activities include a Chuck Wagon with cowboy fixins 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; a western-themed mini golf course; Smarty the Cow Roping Dummy; and a baby goat petting zoo. There will be a ticketed Chili Tasting on Friday night. One of the highlights of the festival is Cowboy Tales, a FREE exhibition at the WCA September 24 through November 15 that illustrates the theme of western culture and imagery. 

WCA plays a key role in bringing cultural programming, exhibitions and entertainment to Winnsboro and East Texas. WCA is supported in part by grants from the Texas Commission on the Arts and the National Endowment for the Arts. Winnsboro’s Cultural Arts District is recognized by the Texas Commission on the Arts for its vibrant arts scene. Winnsboro is also recognized by the National Trust for Historic Preservation as a Texas Main Street Community and an accredited member of Main Street America for its successful downtown revitalization.

For more information about the town’s Cowboy Music and Poetry Gathering, and other cultural events, visit the website.

ABOUT WINNSBORO CENTER FOR THE ARTS: Winnsboro Center for the Arts is a 501(c)(3) nonprofit organization located in Winnsboro, Texas. As a multi-disciplinary arts center, it serves communities throughout Northeast Texas, engaging people in educational programming, cultural experiences, and entertainment. All scheduled programs are subject to change.