Dierks Bentley appears at Cross Canadian Ragweed’s first OSU reunion show
See highlights of the special guest appearances during Cross Canadian Ragweed’s set on Night 1 of the “Boys from Oklahoma” concerts in Stillwater.
Nearly 35 years later, Cody Canada still vividly recalls his teenage years spent at an old Stillwater homestead called “The Farm,” learning his craft from Red Dirt music pioneers.
“When I first went to Stillwater, I was 16 years old and sitting around the campfires, doing as much as I could at The Farm and being around as many people as I could and learning. … Bob Childers told John Cooper that ‘this new batch of kids are all right.’ And that was the blessing,” Canada recalled.
After joining his bandmates in the beloved Red Dirt band Cross Canadian Ragweed in closing out “The Boys from Oklahoma: Round 2” Saturday, April 11, at Oklahoma State University’s Boone Pickens Stadium, Canada is playing one of the final sets Sunday, April 12, at the annual Bob Childers’ Gypsy Café.
“I feel like now we’re the Bob Childerses and the Tom Skinners and the John Coopers: We’re the age that they were when we came to town. And the Oklahoma way is it’s not about you. It’s not about a single person. It’s about a movement of music,” Canada said.
As part of Oklahoma’s largest homegrown songwriter festival, the singer, songwriter and guitarist also will receive the Gypsy Cafe’s Restless Spirit Award Sunday night at Eskimo Joe’s. The award is named for one of the signature songs penned by the late, great Stillwater singer-songwriter Childers, and since 2017, it has been given every year to “a musician who has impacted the Oklahoma music community in a spirit akin to Childers,” who died in 2008.
“It is amazing to me that Bob Childers has an award named after him. I am very honored to be a recipient of my friend’s award,” said Canada, who will turn 50 on May 25.
For the 15th year, the Red Dirt Relief Fund is bringing together 60 Oklahoma songwriters at multiple Stillwater venues for the Bob Childers Gypsy Cafe. The music festival also is the largest annual fundraiser for the nonprofit organization, which provides a safety net for Oklahoma music professionals in need.
“It’s a fun time for everyone to get together … and it’s very rewarding to see the fruits of our labor when you can help somebody who’s really struggling,” said Katie Dale, executive director of the Red Dirt Relief Fund. “It’s more than just music. It’s about the community, and it’s like a family reunion.”
Here’s what to know about the 2026 Bob Childers’ Gypsy Cafe:
When and where in Stillwater is the 2026 Bob Childers’ Gypsy Cafe?
The Bob Childers’ Gypsy Cafe is named for Childers, the Oklahoma songwriter known as the “godfather of Red Dirt music,” and the fanciful nickname for a shed on the grounds of The Farm, the Stillwater homestead where he lived for a time and that now is recognized as the birthplace of Red Dirt music.
After Saturday’s “Boys from Oklahoma: Round 2,” the songwriters festival will cap STOKd, a weeklong showcase for Red Dirt music happening at venues across Stillwater. Named for an acronym for Stillwater, Oklahoma, the celebration is also known as Red Dirt Music Week.
Spread across five Stillwater stages — outdoors at Eskimo Joe’s as well as in
side the recently revived Wormy Dog Saloon, The Dirty Rooster, The Salty Bronc Saloon and George’s Stables — the Gypsy Cafe’s 2026 date was shifted from early May to Sunday specifically to follow Saturday’s “Boys from Oklahoma: Round 2.”
“The phenomenal success of ‘Boys from Oklahoma’ is a testament to the power of Red Dirt music and the impact Red Dirt artists make in Oklahoma. They literally helped start this nonprofit that has since delivered over $1 million in emergency financial assistance to their fellow Oklahoma music creators,” Dale said. “Last year, ‘The Boys from Oklahoma’ drew 200,000 fans from all 50 states to Stillwater. We are so excited to be part of the celebration of this full-circle moment.”
The main festival grounds outside Eskimo Joe’s, plus the other venues open at noon Sunday, with a lineup that features returning favorites like Canada, Mike McClure, Red Dirt Rangers, Carter Sampson, Buffalo Rogers, Caroline Grace, Kalyn Fay, Mallory Eagle, Monica Taylor, Presley Sullins Rains, Dylan Stewart, Mike Hosty and more.
The fest also is adding 13 new voices, along with Sand Springs singer-songwriter Micah Felts, who won this year’s Jimmy LaFave Songwriting Contest with his original tune “I Don’t Know How to Write a Song.”
Hailing from across Oklahoma, the songwriters will gather in small groups to play 45-minute acoustic song-swap sets staggered across the five local venues.
The venues are:
- Eskimo Joe’s, 501 W. Elm St., is all ages and outdoors, weather permitting.
- The Dirty Rooster, 319 S. Washington St., is for ticketholders 21 and older.
- The Salty Bronc, 911 W. Fifth Ave., is for festivalgoers 21 and older.
- George’s Stables, 502 W. Elm St., is for patrons 21 and older, too.
- The Wormy Dog Saloon, 421 S. Washington St., also is for music fans 21 and older.
A free shuttle will run in a loop to the five venues from noon to 7 p.m. Sunday.
What special festivities are planned at the 2026 Gypsy Cafe?
Music will run from 11 a.m. to 11 p.m. Sunday for the Gypsy Cafe fest. General admission tickets are $35 in advance and $40 at the door.
For hungry fans willing to pay extra for extra fun, the Twangers and Bangers Brunch, a 1990s country music showcase presented by an all-star cast of Oklahoma artists, will kick off the festivities at the Wormy Dog. Tickets include a brunch buffet, two drink tickets, $5 off merchandise and general admission to the festival. Doors open at 11 a.m., and music starts at noon.
Gypsy Cafe After Dark, the fest’s official afterparty, will feature Lance Roark at the Wormy Dog. Doors open at 8 p.m.; music starts at 9 p.m. Afterparty tickets do not include general festival admission.
“One of the things that we’re doing this year that we have never done in the past is inviting some other partner nonprofits to be there. So, Our Daily Bread, which is the Stillwater food bank of sorts, is going to be there, selling their merch, talking about their mission,” Dale said.
“We’re trying to shine a light on some of these other organizations that are working every day to support the city and the folks in Stillwater.”
Canada will receive the Gypsy Cafe’s Restless Spirit Award at 6:45 p.m. Sunday at Eskimo Joe’s, where he will play the main stage with friends at 7 p.m.
“Cody Canada is a torchbearer in this scene and has been part of the Red Dirt Relief Fund story from the beginning. He and Cross Canadian Ragweed took this genre on the road three decades ago and became a thread that connects songwriters like his friend Bob Childers to today’s rising Oklahoma talent like Lance Roark and Slaid Cross,'” Dale said.
“Cody and (his wife) Shannon embody the spirit of Red Dirt music, and we are honored that they’ll be with us as Cody receives the Restless Spirit Award and performs at this year’s festival.”
The fest will end with the 7:30 p.m. all-lineup Family Jam Finale on the main stage outside Eskimo Joe’s.
For tickets and information, go to https://www.reddirtrelieffund.org/gypsycafe.
‘ The preceding article may include information circulated by third parties ’
‘ Some details of this article were extracted from the following source www.oklahoman.com ’
