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!

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End Date

Chappell Hill Scarecrow Music Festival

 Saturday, October 10th, 2026 :: 10:00am - 6:00pm
 Chappell Hill Chamber of Commerce

Two days of Texas country music, legendary artists, 100+ vendors and small town heart. All proceeds benefit the Chappell Hill Historical Society, Fire Department & Chamber of Commerce. Music lineup on Saturday includes Roger Creager, Cody Hibbard, The Flinns, Joey McGee, and Cul de Sac.

Chappell Hill Scarecrow Music Festival

 Sunday, October 11th, 2026 :: 10:00am - 6:00pm
 Chappell Hill Chamber of Commerce

Two days of Texas country music, legendary artists, 100+ vendors and small town heart. All proceeds benefit the Chappell Hill Historical Society, Fire Department & Chamber of Commerce. Sunday’s entertainment lineup includes Bri Bagwell, Black Cat Choir, Cathey Bolin & Henry Williams, Cooper Mohrmann, and Taylor Graves. Ten acts over two days on three stages.

Texas Arts & Music Festival

 Friday, October 16th, 2026 :: 12:00am - 12:00am
 Texas Arts and Music Festival

Live music, live murals, art village, and more! This free festival offers something the whole family can enjoy. Music groups include The Last Bandoleros, Henry Invisible, The Guzzlers and Phil ‘N The Blanks Jazz Band. Each year a new mural will be painted on a downtown building.

Texas Arts & Music Festival

 Saturday, October 17th, 2026 :: 12:00am - 12:00am
 Texas Arts and Music Festival

Live music, live murals, art village, and more! This free festival offers something the whole family can enjoy. Music groups include The Last Bandoleros, Henry Invisible, The Guzzlers and Phil ‘N The Blanks Jazz Band. Each year a new mural will be painted on a downtown building.

Home Free

 Saturday, October 17th, 2026 :: 7:00pm - 9:00pm
 Barnhill Center at Historic Simon Theatre

Named “country music fans’ favorite a cappella group” by Taste of Country. Upbeat Nashville-dipped pop hits, country and western standards, stunning harmonies and quick-witted humor. These Grand Ole Opry and TV stars have a busy worldwide tour schedule. They amassed over 1.8 million YouTube subscribers and released twenty Top 10 Hits.

Tickets: $90 – $105

Sponsored by Bill Kaminer

Texas Arts & Music Festival

 Sunday, October 18th, 2026 :: 12:00am - 12:00am
 Texas Arts and Music Festival

Live music, live murals, art village, and more! This free festival offers something the whole family can enjoy. Music groups include The Last Bandoleros, Henry Invisible, The Guzzlers and Phil ‘N The Blanks Jazz Band. Each year a new mural will be painted on a downtown building.

Out of Pocket Theatre – Almost, Maine by John Cariani

 Thursday, October 22nd, 2026 :: 7:00pm - 5:30pm

Welcome to Almost, Maine, a place that’s so far north, it’s almost not in the United States. It’s almost in Canada. And it’s not quite a town, because its residents never got around to getting organized. So it almost doesn’t exist. One cold, clear, winter night, as the northern lights hover in the star-filled sky above, the residents of Almost, Maine, find themselves falling in and out of love in unexpected and hilarious ways. Knees are bruised. Hearts are broken. But the bruises heal, and the hearts mend – almost – in this delightful midwinter night’s dream.

Thursday (10/22) – Saturday (10/24): 7pm
Sunday (10/25): 5:30pm

Tickets are $10 for adults, $8 for Seniors (65+), $6 for students, and $5 for kids under 12. Tickets available October 1st online at www.outofpocketbrenham.org or at the door the day of the event. Content Advisory: Recommended for ages 10+. Contains themes of romance, brief kissing, mild language, and discussions of adult relationships. Almost, Maine is presented by arrangement with Concord Theatricals on behalf of Samuel French, Inc. www.concordtheatricals.com

Antiques@ the pavilions

 Friday, October 23rd, 2026 :: 12:00am - 12:00am
 Texas Cotton Gin Museum

Come shop Antiques @the Pavilions for great dealers, covered shopping, free parking and more October 23 to November 1st from 9am to 5pm. Late night shopping and fun Friday, October 30th for the Wine & Wander from 6-9pm. RV spaces available for rent on the lower field call 979-289-3378. Visit https://www.facebook.com/events/3232892176894825/.