Trivia Night
August 18, 2026
ALL EVENTS IN WINNSBORO
NEXT ANNUAL EVENT
Mark Your Calendars for September 25 & 26
Saddle up for the Winnsboro Cowboy Music and Poetry Gathering, September 25–26, 2026, in historic downtown Winnsboro. This two-day celebration of Western heritage features cowboy poetry, live music, storytelling, art, family-friendly activities and plenty of small-town hospitality on The Bowery. Additional Information
EXPLORE WINNSBORO
ART AND MUSIC
Art and music are at the heart of Winnsboro’s charm. From live concerts and theatre performances to art classes, music lessons, gallery exhibits, and community events, there is always something creative happening in town. The annual Art & Wine Festival brings artists, musicians, visitors, and neighbors together to celebrate local talent, great food, wine, and small-town hospitality.
FARMERS MARKET
The award-winning Winnsboro Farmers Market is a favorite Saturday morning gathering place, bringing together local growers, makers, bakers, artisans, and neighbors in the heart of town. Visitors can shop for fresh produce, homemade goods, flowers, crafts, and seasonal specialties while enjoying the friendly small-town atmosphere that makes Winnsboro so special.
RESTAURANTS AND SHOPPING
Shopping in Winnsboro is part of the fun, with locally owned boutiques, antique shops, gift stores, art, home décor, and one-of-a-kind finds throughout town. Visitors can spend the day browsing, discovering treasures, and supporting small businesses while enjoying the charm and hospitality that make Winnsboro such a special destination.
ANNUAL EVENTS
Winnsboro’s annual events bring the community together and welcome visitors throughout the year with festivals, concerts, markets, holiday celebrations, art events, parades, and family-friendly activities. From long-standing traditions to seasonal gatherings, these events showcase the creativity, hospitality, and small-town spirit that make Winnsboro a memorable place to visit.
AUTUMN TRAILS
Autumn Trails is one of Winnsboro’s most beloved fall traditions, celebrating the beauty, history, and small-town spirit of East Texas. Each year, visitors and residents enjoy a season of classic cars, parades, trail rides, scenic drives, music, food, vendors, and family-friendly events that bring the community together and welcome guests from near and far.
WELCOMING COMMUNITY
Winnsboro is known for its genuinely welcoming community, where the first time you visit you may arrive as a stranger, but the next time you are greeted as a friend. People here care for one another, show up in times of need, and are quick with a smile, a hug, or an invitation to join in. From live music at local restaurants to card games, Mahjong, Trivial Pursuit nights, and casual gatherings, Winnsboro makes it easy to build friendships and feel at home.
WINNSBORO CENTER FOR THE ARTS CREATIVE LEARNING CENTER
The new Winnsboro Center for the Arts Creative Learning Center marks an exciting expansion of Winnsboro’s growing Cultural Arts District. Celebrated with a ribbon cutting in 2026 after groundbreaking festivities in August 2024, the center gives WCA more room to offer art classes, music and voice lessons, ceramics, workshops, youth programs, and creative opportunities for all ages. It is another beautiful step forward for a community that believes the arts belong at the heart of everyday life. Visit the Winnsboro Center for the Arts
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Winnsboro is one of the most vibrant towns in Texas. It is also one of the friendliest towns and attracts exceptional businesses and restaurants.
Many weekends are filled with unique events, music and art. Twice a month receive our Newsletter and stay informed about all the activities in the community.