Chisholm Trail Festival 2026

The fun kicks off Friday, May 1st! Spend the day exploring all the self-guided activities at your own pace, then wrap up the night in style with our Roaring 20’s Pub Crawl… six stops, one block on Main Street in Caldwell, and a whole lot of good times packed into a single ticket. On Saturday, The Farmer's Market kicks off as a gathering of makers and crafters will display their wares at the Caldwell Community Building. This will join a Western Art Show and outdoor Kid Korral activities! Kick off Saturday at the Opera House, catch the cattle drive down Main Street, and don’t miss the high noon gunfight and Red Hills Bi-State Race. Afternoon is a a choose-your-own-adventure and Live music kicks off at 5:00pm and rolls all the way through 11:00pm. For more information visit, caldwellkansas.com or the Chisolm Trail Festival Facebook Page.