October at Oaklea Mansion: Fall Fun in Winnsboro

October is upon us, and it’s one of the busiest, most beautiful times of the year in Winnsboro and at Oaklea Mansion. With cooler temperatures, crisp autumn air, and leaves beginning to fall, there’s no better season to book your stay with us.

Not only is Oaklea Mansion a retreat of comfort and elegance, but it’s also right in the heart of all the excitement. Winnsboro comes alive in October with the beloved Autumn Trails Festival, drawing visitors from across Texas and beyond.

Here’s a look at what’s happening this month:

🍂 October Autumn Trails 2025 Highlights

• Saturday, October 4

  • Antique Tractor Show & Pull – 8:00 am, Jack Cross Pavilion

  • The 5K – 9:00 am, Winnsboro City Park

  • Fun Run & Walk – 10:00 am, Winnsboro Civic Center

  • Autumn Trails Pageant – 6:00 pm, Winnsboro Jr. High

    
    

• Saturday, October 11

  • Just Believe’s Western Playground – 7:00 am, Jack Cross Pavilion

  • SS Elite Youth Rodeo – 8:00 am, WRA Rodeo Arena

    
    

• Friday, October 17

  • Trail Ride Welcome Parade – 4:00 pm, Water Tower

    
    

• Saturday, October 18

  • WHS Battle of the Spear – 8:00 am, Red Raider Stadium

  • Trail Ride – 10:00 am, City Park

  • 42 Tournament – 11:00 am, Civic Center

  • Cake & Pie Baking Contest – 12:00 pm, Civic Center

  • Mule Rodeo – 7:00 pm, WRA Rodeo Arena

  • Barn Dance – Following the Mule Rodeo, Civic Center

    
    

• Thursday–Friday, October 23–24

  • Trades Day & Swap Meet – Friday at 1:00 pm, Saturday 7:00 am–5:00 pm, City Park

    
    

• Saturday, October 25

  • Arts & Crafts Show – 8:00 am–5:00 pm, Elm & Market

  • Christ’s FREE Flu Shot Clinic – 8:00 am–5:00 pm, Elm & Market

  • Antique Car Parade – 10:00 am, Hwy 11

  • Classic Car Show – 11:00 am, South Main Street

  • Fashion Through the Eras – After the parade, 215 N Main St

  • All School Reunion – 11:00 am, Rock Gym

  • Lone Star Pepper Palooza – 1:00–4:00 pm, Farmers Market

  • Model A BBQ – 5:00 pm, Civic Center

    
    

• Sunday, October 26

  • Trades Day & Swap Meet – 7:00 am–3:00 pm, City Park

  • Model A Tour – 9:00 am, Trails Country Motel

    
    

• Friday, October 31

  • Trunk or Treat – 5:00 pm, Downtown Winnsboro

    
    

✨ Whether you’re here for the classic cars, the mule rodeo, or just the small-town charm, Oaklea Mansion is the perfect place to stay during the festivities. After a day of exploring, return to the Mansion to relax in luxury, sip something warm on the porch, and enjoy the season.

👉 Book your October getaway today—rooms fill quickly during Autumn Trails!