Caldwell Chisholm Trail Festival

Caldwell Chisholm Trail Festival Celebrating Caldwell's Wild West history, annually every first full weekend in May in Caldwell, Ks. Talk about making a statement! Welcome to town!

Sponsored by Caldwell Ks Chamber of Commerce and Caldwell Historical Society Welcome to Caldwell, the “Border Queen” and a true child of the Trail, born due to her location on the Trail. Though established in 1871 by opportunity-seeking Wichita businessmen to set up shop on the border of Indian Territory, there was a general store/dance hall here on the border in 1869 called The First Chance/Last

Chance Saloon for the weary cowboy after months of driving the Chisholm Trail from Texas. “First Chance” for thirsty young cowboys from the south, but “Last Chance” for liquor and supplies for those same cowboys heading back south through Indian Territory. True grit formed this trail town, with 4 murders, 2 lynchings, and a classic gunfight in its first year. By year 3, they were trying out their 9th marshal, only to quickly need a 10th. It remained little more than a trading post until the Santa Fe Railroad extended its line to Caldwell in 1879. This rail restored the idle Chisholm Trail back to its glory days, bringing more than a million longhorns thru town. During its reckless cowtown period between 1879 and 1885, Caldwell boasted a higher murder rate and loss of more law enforcement officers than other more famous cowtowns. Life was rough, but a glorious place for villains and desperados to escape to lawless Indian Territory. As you can imagine, it provided a place for young cowboys to go wild after long months on the trail, sampling the 14 saloons, brothels, and gambling dens to see if they could make it out alive! Gunfights, showdowns, general hell raising and hangings soon became commonplace. Finally a glimmer of hope arrived in 1882; Henry Brown saved the day, becoming our marshal after riding with Billy the Kid, acquiring skills to wrangle a rustler and unarm a gun slinging drunkard. Peace was kept until he rode west to Medicine Lodge with his deputy Ben Wheeler and two others, attempting to rob their bank. They killed two bank employees though rode away with no cash. Later in the night, after the gang was arrested, Brown was shot by a raging mob that broke into the jail, and Wheeler was shot AND hung to die. Caldwell settled down until 1893 when Congress opened the Cherokee Outlet to the south for settlement. Soon, the town was filled with thousands of land hungry pioneers preparing for the last great land rush in America. At high noon on Sept 16, 1893, thousands gathered in Caldwell, awaiting the cavalry soldiers’ gunshots to start the mad rush for land. Today, it’s a quiet agricultural community of 1,000 settlers with an Opera House, museum, silhouettes on the southern bluffs, a new Turtle Trail, and historical walking tour signs to guide you through our raucous youth. The Chisholm Trail is celebrated every first weekend in May where we relive our Wild West days with pub crawling, ghost tours, gambling parlors, gunfights, saloon girls, and opera house shows. We’re friendly now.

As America250 celebrates this year, let's tip our hat to the historic cattle trails!  After the fallout of the brutal Ci...
05/11/2026

As America250 celebrates this year, let's tip our hat to the historic cattle trails! After the fallout of the brutal Civil War, these cattle trails built towns -- towns that built America as we expanded westward.

Caldwell Chisholm Trail Fest fired the torch on May 2, 2026 to continue sharing the resolution introduced by US Congressman Ron Estes in honoring the American Cowboy and the historic cattle trails that sparked the important economic impact, beef distribution to eastern markets, and railhead decisions.

Please carry and pass the torch, acknowledging the historic cattle trails and American Cowboy as we celebrate the and the other historic trails --Shawnee Trail, Goodnight-Loving Trail, Western and Great Western Trail -- at our annual festivals from Texas to Kansas throughout 2026!! San Antonio to Cleburne to Fort Worth; to Duncan, Yukon, Kingfisher, OKC and Enid; to Caldwell, Clearwater, Wichita's Cowtown, Dodge City, Ellsworth, Newton, and Abilene!

US Highway 81 closely followed the historic Chisholm Trail because the trail was well-travelled and known nationwide. Celebrate with us as we share all of the festivities up and down the Chisholm Trail during America's 250th Anniversary celebration year!

05/11/2026

More fun along the historic Chisholm Trail!

Creative Vibes Art Studio and Caldwell Art Brigade hosted an art show at the Fest, with special guest artist, Alan Colli...
05/11/2026

Creative Vibes Art Studio and Caldwell Art Brigade hosted an art show at the Fest, with special guest artist, Alan Collins from Leavenworth, Ks. Alan also spoke at the Opera House about his art process, his lifelong interest in art, and how he switched careers to pursue art full-time. He sold a handful of beautiful oil paintings during the show—two will live on in Caldwell and one in Arlington, Texas!

This show also hosted pieces from Caldwell Schools art students, the 8th grade poetry class who wrote about the Chisholm Trail, and collage art depicting Wild West, infamous characters of Caldwell.

Creative Vibes Art Studio is a working studio, hosting instructional paint classes and special event “paint & sip” and birthday parties for kids. Caldwell Art Brigade is a local volunteer group that paints tall buildings in a single bound.

The Al Express was a hit during the Chisholm Trail Fest! Emma Rohrbaugh, a Caldwell Schools student, programmed their ro...
05/11/2026

The Al Express was a hit during the Chisholm Trail Fest! Emma Rohrbaugh, a Caldwell Schools student, programmed their robotic “turf tank” to create a train track on street. Dean Owens conducted the train, giving rides all afternoon! Al Melichar’s train rides will continue to thrill kiddos in memory of a wonderful soul Caldwell was privileged to know.

Kelsey Weems and her Impact Bank team provided phenomenal fun at the Kid Games event! The middle school scavenger hunt was a hit!
**We are looking for photos of Mutton Bustin event, share if you have any please 🤞

And for the icing on the cake, the grand opening of Ollie's Ice Cream & Soda Shop was a treat for the whole town!! Kid-approved!!

BIG THANKS to Kansas’ US Representative Ron Estes for introducing his resolution to honor the American cowboy in America...
05/05/2026

BIG THANKS to Kansas’ US Representative Ron Estes for introducing his resolution to honor the American cowboy in America’s 250th anniversary year, and the significance and contributions of the historic cattle trails that built our country.

The Chisholm Trail built Caldwell, and we are grateful for Congressman Estes’s efforts over the years to help build momentum in nationalizing these economic and infrastructural trails that built in America!!

Congressman Ron Estes

Friday at the Fest, we welcomed Patricia Ann McNight to share her book based in Caldwell!! The Caldwell Public Library h...
05/05/2026

Friday at the Fest, we welcomed Patricia Ann McNight to share her book based in Caldwell!! The Caldwell Public Library hosted at 1pm. Her husband shared Patricia’s great grandfather lineage here, buried in our local cemetery, and presented his the GAR veteran member book to the Caldwell Historical Society for their connection. It was a joy meeting them!!

The Border Queen Regulators make their own ammo blanks to reenact the regular downtown gunfights. Big thanks to David Te...
05/05/2026

The Border Queen Regulators make their own ammo blanks to reenact the regular downtown gunfights. Big thanks to David Teeter for corralling the gang!!

The Chisholm Trail Racers!! This Red Hills, 2-state run is 13-mile half marathon. Big thanks to all who participated and...
05/05/2026

The Chisholm Trail Racers!! This Red Hills, 2-state run is 13-mile half marathon.

Big thanks to all who participated and to Cale & Kambree Reber for leading the charge!! Next year, it will begin at 9:00 am to avoid the heat.

Cool drone shots of the 2026 Caldwell Chisholm Trail Cattle Drive! We tip our hat to Roy Andreas for capturing these!
05/05/2026

Cool drone shots of the 2026 Caldwell Chisholm Trail Cattle Drive! We tip our hat to Roy Andreas for capturing these!

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Caldwell, KS
67022

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