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Downtown Winnsboro TX during Autumn Trails Antique Car Weekend

Welcome to Winnsboro TX

Heritage Highlights

The Bowery
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Winnsboro Cowboy Music & Poetry Gathering

September 25-26, 2026

The Winnsboro Cowboy Music & Poetry Gathering is a two-day celebration of Western heritage featuring cowboy poetry, live music, storytelling, and family-friendly activities. Held at the Bowery Stage in downtown Winnsboro, the event brings talented performers and artists together to honor the traditions and spirit of the American West.

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Winnsboro Autumn Trails

October 2026

The Winnsboro Autumn Trails Festival is a beloved fall tradition celebrating the town’s heritage and community spirit. Held each October, the festival features parades, live music, arts and crafts, local food, and family-friendly events that bring visitors and residents together for one of East Texas’s most cherished celebrations.

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Winnsboro BLOOM!

April 11-25, 2026

BLOOM is a spring celebration in Winnsboro, Texas, that transforms the town into a vibrant showcase of art, flowers, and creativity. Hosted by the Winnsboro Center for the Arts, the multi-week event features art exhibits, window displays, concerts, tours, and community events that celebrate the season and attract visitors to downtown.

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Taste of Winnsboro

COMING 2026!

A Taste of Winnsboro is a flavorful celebration of the town’s local restaurants and culinary talent. Visitors can sample dishes from a variety of Winnsboro eateries while enjoying live music and a lively community atmosphere, making it a delicious highlight of the town’s annual events and cultural celebrations.

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Winnsboro Arts & Wine Festival

November 6-7, 2026

The Winnsboro Art & Wine Festival is a lively fall celebration in downtown Winnsboro that brings together fine art, Texas wineries, live music, and local food. Visitors can explore juried artwork from talented artists while enjoying wine tastings and entertainment in the heart of the town’s Cultural Arts District.

Timeless Hospitality:
Meet Your Curator, Oaklea Mansion

Step into the storied halls of Oaklea Mansion, Winnsboro’s oldest historic stay and the cornerstone of local hospitality. As the official curator of the Getaway to Winnsboro, Oaklea offers more than a place to rest—it is your gateway to small town Winnsboro, Texas.

Whether you are reclining in our majestic suites or using our guide to map your journey, we believe every visitor deserves an immaculate experience. From handcrafted itineraries to a showcase of Winnsboro’s small businesses, Oaklea is your starting point for a truly local adventure.

Stay with us for a taste of history, or let our guide help you find your perfect Winnsboro fit.

Oaklea Mansion_The Carlock House
Breakfast Setup at Oaklea Mansion
The Carlock House Museum
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