Autumn in Winnsboro

A Magical Time of Year

As the days get shorter and shorter and the nights get cooler and cooler something magical is about to happen in Winnsboro: Autumn Trails! The festival began when a few friends gathered on a cool, crisp October morning in 1958 to enjoy the beautiful fall foliage in the area on horseback. What started that Sunday morning 63 years ago can only be described as legendary.

      The 2021 Autumn Trails will have the blending of the old with the new. Many old events have been  revived and new events are being added to the lineup.   

New for 2021 is Jeeptober in the 'Boro', a Jeep show and shine at the Depot and cruise in the fall foliage. We are also bringing back the Beard and Mustache contest, and Bands on the Bowery. Stay tuned to this sight and our social media pages for details. We hope to see you in Winnsboro in October!


Autumn Trails 1965, Con Jordan and grandson AT Board Member Mack Jordan enjoy the Duncanville to Winnsboro Trail Ride. According to Mack the team belonged to Lundy Corley, and he was 2 years old at the time.

October is a magical time of year in Winnsboro! The history. The fun. The memories. That's what makes Winnsboro Home of the Autumn Trails for 63 years. 2021 promises to be just as chocked full of activities. Check back often for updates and information!



     The Autumn Trails Association would like to thank the Winnsboro Economic Development Corporation, the City of Winnsboro, TransCanada and our sponsors and supporters for making 2020 a successful year.​