Family, friends and visitors all enjoy popular events that are planned throughout the year. Wine Walks, Fun Runs, Festivals and Fairs put smiles on faces young and young at heart!
Annual Teddy Bear Parade
Saturday, December 13th, 2025 :: 3:30pm - 5:00pm
Chappell Hill Chamber of Commerce
Bring your kiddos to downtown Chappell Hill for our annual Teddy Bear Parade. Lots of fun activities for the children. Sit and talk to Santa, bring your Teddy Bear for the parade. Don’t miss this free event for the little children. More details to come.
Paint & Sip at Chapelton Vineyards
Sunday, December 14th, 2025 :: 11:00am - 12:30pm
Chapelton Vineyards
Join us for a fun and artsy experience at Chapelton Vineyards, led by the talented The Paint Lady! Whether you’re an experienced artist or just looking to try something new, this relaxed and inspiring class is the perfect way to unleash your creativity—no experience necessary!
With step-by-step guidance, you’ll create your own unique masterpiece while sipping on a glass of one of Chapelton’s finest wines. It’s the perfect blend of art, wine, and great company in a beautiful vineyard setting.
Top of the World, A Carpenters Christmas
Saturday, December 20th, 2025 :: 7:00pm - 9:00pm
Barnhill Center at Historic Simon Theatre
A beautiful Christmas show, musically and visually, combined with the unforgettable pop hits of the Carpenters. The 8-piece band of world class musicians is fronted by Debbie Taylor, whose vocal resemblance to the great Karen Carpenter is absolutely astonishing.
Tickets: $95 – $110
Burton Cotton Gin Festival
Saturday, April 18th, 2026 :: 10:00am - 6:00pm
Texas Cotton Gin Museum
Come celebrate history in the making at the 37th Annual Burton Cotton Gin Festival on Saturday, April 18th, 2025. This charming small-town Texas festival is FREE and family-friendly, featuring a parade, live music, contests, games, arts and crafts, delicious food and drinks, an antique tractor pull, an engine show, and classic cars on display.