Winnsboro Autumn Trails or Bust—65 Years Running

Try and visualize 300 Model A cars from 1940 lined up in a row and people in old-timey hats and scarves, smiling as they drive through downtown. Or, maybe even better, 1,000 proud, tall horses, ridden by straight-backed, Southern-accented cowboys and cowgirls from across the state.

Well, it’s not out of the realm of possibility. After all, it’s what happened last year.

Luckily, the Winnsboro Autumn Trails Association brought back both wildly successful events this year. Autumn Trails is a series of events attended by thousands from across the country. The events are held in Winnsboro on weekends throughout the month of October, but most events are held on the last two weekends of October.

The classic car parade, held on Saturday, October 28, was a fun and popular Route 66-esque event. “I know we had, at one time, more than 300 Model A Fords,” says ‘Tex’ Willis, the president of the Winnsboro Autumn Trails Association. 

This car parade has held the record for the biggest parade of its kind in Texas, but the tradition of holding a Model A car parade in Winnsboro started in an obnoxiously comical way. In October of 1963, two Winnsboro friends decided to take their decorated Model As, paint “Winnsboro or Bust” on the side, and go around downtown honking and waving.

“Imagine if you will, shopping the sidewalk sales of downtown Winnsboro in October 1963, and you hear the sounds of an ‘aoogah’ horn, and see two old Model A Fords round the corner and barrel down Main Street,” said the 2022 Autumn Trails brochure.

One of the friend’s brothers told him that the display was embarrassing (even though those viewing the “parade” were having as much of a blast as the two friends were). Soon, however, the brother decided to get a Model A and join the parade, too. 

Now, the Model A car parade has become a 60-year, annual tradition, attended and loved by hundreds. It’s even branched out into allowing other types of old cars to attend.

The horse parade is wildly popular as well: much more than a simple one-time ride, the Trail Ride is a three-day blowout. The “Trail Ride” weekend is actually almost more like an Old West re-enactment, with its paraders camping out in tents and wagons, surrounded by their horses and mules. 

Organizers of this event work very hard to live up to expectations. The legacy is long and honored, since the Winnsboro Autumn Trail Ride weekend actually holds the record for being the two largest trail rides in the entire state of Texas. 

The trail ride starts out with a welcome parade. “That’s just to kind of welcome ‘em here to town,” says Tex with a smile. And the fun picks up from there. Over the next day or two, participants set off on a 20-mile trail ride, then are treated to a hilarious “mule rodeo” that evening.

If you think those are great, wait until you find out that the Winnsboro Autumn Trails Festival has many, many other popular, fun, and wholesome events lined up for 2024. After all, it’s the 66th anniversary. Why not have more than 30 contests, shows, and events? 

Pie and cake baking contests, a youth rodeo, live bands, and an arts and crafts show are some of the events. For the not-faint-of-heart, there’s also a hot sauce contest, a hot pepper eating competition, and a pepper recipe dishes contest!

“I brought back some of the old stuff,” says Tex. “We try to make sure we have something for everybody.”

Almost every event is free, so bring the whole family, get out, and enjoy what will hopefully be finally nice October weather!