By Brynna Williamson
Autumn. Ahhhhh. The season of pumpkin spice, flannel shirts, bonfires, and spooky decorations.
Honestly, here in Wood County, Texas, it’s the time of year that we get some of the most community, too—that perfect time of year where the weather is so, so wonderful that you can’t help wanting to get out, walk around, and do something fun.
The heat of summer is fading, and the relief of sunny, brisk fall is here. That feeling is exactly what Winnsboro’s Autumn Trails Festival has celebrated for 67 years now.
The “Deets”
Okay. You would think, because I’m writing this article, that I’m going to make this event sound bigger than it really is, but I’m not. 2025’s Autumn Trails really is the coolest, coolest thing, and I am personally excited to go.
“They are bringing back a lot that we haven’t had (in a long time),” said Carolyn Stout, Main Street Manager for Winnsboro.
You hear sometimes that an event has “something for everybody.” Well, many events may, in actuality, or may not, have something for everyone. Autumn Trails, however, actually does. The variety of what Winnsboro offers during the four weekends in October is insane.
Beauty pageants.
A mule rodeo (which is Hilarious with a capital H. You absolutely cannot miss this! Imagine trying to convince stubborn donkeys to do barrel racing, and you’ll get the upshot of this uproarious, laughter-inducing event).
A hot pepper eating contest.
Vendors, arts, and crafts.
Food trucks.
A playground for kids.
A school reunion for anyone who ever went to school in Winnsboro.
A fashion show. (I’m telling you, there’s literally something for everyone.)
A beard and mustache contest.
There is literally so much to see—so much that I feel I can hardly miss a single weekend of this wonderful Wood County tradition. Oh, and by the way, these are just a few of the events; there are more, too.
And yet, none of this even touches on Winnsboro’s classic Autumn Trails events, each of which is imbued with a funny, local, well-beloved history.
The Classics
For example, the Model A Club. Classic car shows happen with relative frequency around Wood County, Texas, but if you’ve heard of Winnsboro’s unique twist on an old concept, you’ll know how this uber-popular thing came about.
In 1963, Winnsboro residents Robert “Uncle Bob” Willis and J.B. Vaughn, trying to be mischievous and silly, accidentally started a tradition when they took an “old junky car,” painted “Winnsboro or Bust” on the side, and careened around town, honking and waving at people.
“Imagine if you will, while shopping the sidewalk sales of downtown Winnsboro in October 1963, you hear the sounds of an ‘aoogah’ horn, and see two old Model A Fords round the corner and barrel down Main Street,” says the Autumn Trails brochure from a few years ago. Everyone loved it—except Uncle Bob’s brother John, who thought it was all embarrassing. Uncle Bob was persistent, however, and when he brought John to a Model A club and John ended up purchasing a Model A for himself, the unofficial Model A club was formed.
“He joined the club and got him a Model A; then it wasn’t so ‘embarrassing,’” laughed Tex Willis, the son of Uncle Bob and himself a previous Autumn Trails President.
More and more people began to want to be part of the tradition. In recent years, the Model A Club car show has featured about 150 Model A cars, which are added to another 150 other antique and classic cars for the beloved car parade!
Or, for another classic event, take for instance the trail rides. As you can see by the name, this series of events is really the central figure to the Autumn Trails Festival (although it wouldn’t be a proper “Autumn Trails” without many other things, too). The trail rides began in 1958, when previous Winnsboro News editor Harold Rosser decided, along with some of his friends, to go on a long ride through the backwoods of East Texas to enjoy the peace and extraordinary beauty of the turning leaves.
In the same way that the Model A Club started—someone wanted to do something, and others joined in one by one over the years—a new tradition was formed. “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 65 years ago can only be described as legendary,” says the Autumn Trails website.
Today, trail riders get to camp out together, make friends, reunite with last year’s friends, and generally enjoy themselves with Autumn Trail activities, until participating in the trail ride parade on Friday (this year, the 17th of October). Then, on Saturday, the real star of the event begins: the trail ride itself.
Covering almost 17 miles from Winnsboro City Park to Lake Winnsboro, the trail ride is really just a chance for people to experience stunning East Texas tranquility and autumn beauty while on horseback or in wagons. A throwback to a different, slower time, the trail ride has proved immensely popular, bringing in between 500 to 1,000 people a year to enjoy the event. Legendary indeed!
The Plan
As we all know, many times a news or media organization will post a “review” of something, where you only hear about how much fun you missed afteran event is already over. By publishing this story about Winnsboro’s Autumn Trails Festival ahead of time, we at LoveWoodCounty.com are trying to avoid that. To you, our readers, we say, “Go and enjoy this free event!” Fall is such a magical, special, simply fun time of year, so go spend it doing something you’ll enjoy and remember! Put Winnsboro’s Autumn Trails Festival on your calendar now, while you’re thinking about it; and if, by some chance, you don’t read this story until the event is over (by the way, Autumn Trails runs every weekend in October—for more information and a full schedule of events, visit the website), then don’t worry a bit; it’s coming next year, too!