Saddle Up for the Winnsboro Cowboy Music & Poetry Festival

By the end of September, we’re all secretly hoping for sweater weather, campfires, hot chocolate, and maybe even a little mulled cider. But while the leaves are just barely starting to hint at turning, Winnsboro is already saddling up for something even better: The 2025 Winnsboro Cowboy Music & Poetry Gathering, happening September 26–27.

Every year, this festival grows bigger, bolder, and more fun, and this year promises to be no exception. Hosted by the Winnsboro Center for the Arts, this two-day celebration of Western and cowboy culture is packed full of music, poetry, food, and family activities that honor the traditions of the American West.

Friday, September 26 – Cowboy Conversations & Chili Cookoff

Friday kicks off with some of the best in cowboy storytelling and music:

• 1 PM – Cowboy Culture Conversations - Andy Hedges and Pipp Gillette will sit down to talk about how ranch life influenced Pipp and his late brother’s music and poetry. This is the kind of conversation where you’ll find yourself nodding along like you’ve been out on the range your whole life.

  
  

• 4 PM – Cowboy Poetry & Music - Hear from Jay Snider, Teresa Burleson, and Bob Campbell, alongside performances from Pipp Gillette, Kristyn Harris, and Andy Wilkinson. These artists don’t just sing and recite words; they transport you right into the heart of cowboy life.

  
  

And because no cowboy gathering is complete without food, Friday evening also features a Chili Cookoff. Be sure to come hungry!

Meanwhile, from 12–6 PM, vendors will be out on the Bowery with plenty of goods, gifts, and fun finds.

Saturday, September 27 – A Day Full of Family Fun (and Mule Wagon Rides!)

Saturday is the big family day, and the best part? Most activities are FREE.

Starting at 10 AM, regional performers take the stage on the Bowery, while vendors set up shop again with everything from handmade goods to Western treasures. Activities include:

• Smarty the Calf Roping Dummy – kids (and brave adults) can try their hand at roping skills.

• Face Painting & Mini Golf – something for the little ones and the young at heart.

• Mule Wagon Rides with Gus & Woodrow – always a fan favorite.

• Chuckwagon Cooking – taste authentic beans, cornbread, and cobbler.

• Los Diablos Tejanos (Texas Ranger reenactments) – living history you won’t want to miss.

• Chainsaw Carving Demos – watch artistry meet horsepower.

• Whisky the Horse & Goat Petting Zoo – plenty of photo ops and furry friends.

  
  

The main stage performances include:

• 1 PM – Cowboy History & Stories with Andy Wilkinson and Andy Hedges.

• 4 PM – Western Swing with Kristyn Harris Trio (get ready to tap your boots).

• 7 PM – Carnegie Hall Cowboys cap off the night with classic cowboy music and poetry.

  
  

This is more than just a festival — it’s a celebration of heritage, history, and the cowboy spirit that built the West.

Make Oaklea Mansion Your Festival Headquarters

After a day full of music, mule rides, and chili, you’ll want a soft bed to fall into. That’s where we come in. At Oaklea Mansion Bed & Breakfast, you’ll step back into history while enjoying timeless Southern hospitality.

We’re just a short stroll from all the action in downtown Winnsboro, making Oaklea the perfect spot to rest your boots after the festival. Rooms do book up quickly this time of year, so if you haven’t already reserved yours, now’s the time.

 Don’t miss your chance to enjoy the Cowboy Music & Poetry Festival in true Winnsboro style. Book your stay at Oaklea Mansion today and make this weekend one to remember.