Media release
-How to hear 100 Oklahoma musicians and see the presentation of the Red Dirt Relief Fund’s Restless Spirit Award to Cody Canada-
March 25, 2026— Bob Childers’ Gypsy Café, Oklahoma’s largest homegrown songwriter festival, has released the schedule of 100 Oklahoma musicians playing across five stages in Stillwater on Boys from Oklahoma weekend, April 11-12, along with the presentation of the 2026 Restless Spirit Award to Cody Canada. Now in its fifteenth year, the festival benefits Red Dirt Relief Fund, the nonprofit that has provided more than $1 million in emergency financial assistance to music professionals in all genres statewide since 2012.
Saturday, April 11th: Gypsy Café Preview
Fans of all ages warming up for the Boys from Oklahoma concert are invited to a free, all-ages stage outside Eskimo Joe’s for full-band performances from The Heard (12pm), Kanton Teen & the Penny Pickers (1pm), Joleen Brown (2pm), Thomas Trapp & Friends (3pm) and The Brothers Moore (4pm).
Sunday, April 12th: Bob Childers’ Gypsy Cafe
With five stages at live music venues around Stillwater, festival organizers are providing a free shuttle to help attendees make their way to hear 60 of Oklahoma’ best songwriters perform acoustic song swap sets throughout the day. The festival is also providing a free shuttle that will run a loop around festival venues from 12-5pm. See the schedule and purchase tickets at www.reddirtrelieffund.org/gypsycafe.
Sunday’s festivities will kick off at noon with Twangers and Bangers Brunch presented by Cove Environmental. Hosted by husband-and-wife powerhouses, Sydney Jennings and Jake Lynn (drummer for Wyatt Flores), this 90’s country tribute will feature vocalists Cassie Latshaw, Amber Watson, Jacob Tovar and Jared Tyler. The festival ends with Gypsy Café After Dark, an afterparty featuring the electric country soul of Lance Roark at The Wormy Dog. These two events are not included with General Admission tickets.
Restless Spirit Award: Cody Canada
At the Grand Casino Main Stage at Eskimo Joe’s on Sunday, Cody Canada will be honored for his contributions to Red Dirt music that span more than three decades. His career began in Stillwater as a founding member of Cross Canadian Ragweed in 1994. Inspired by mentors like Bob Childers and The Great Divide, Canada helped define the red dirt genre as a misfit blend of rock, country, and blues that refused to fit the Nashville mold. Ragweed’s success in the late 90s and 2000s helped propel the Oklahoma scene into Texas and beyond, paving the way for artists like Turnpike Troubadours. After Cross Canadian Ragweed broke up in 2010, Canada continued to be a major figure in the scene, forming Cody Canada & The Departed in 2011. Canada performed at the inaugural Gypsy Café in 2011, the event that launched Red Dirt Relief Fund, and again in 2016, 2017, 2020 and 2023.
Fueled by the reunion of Cross Canadian Ragweed in 2025 and the efforts of Shannon and Cody Canada, four Boys from Oklahoma concerts held at Boone Pickens Stadium in April 2025 drew 200,000 music fans to Stillwater from all 50 states, creating an economic impact similar in scope to festivals like Coachella. Last year the band was inducted into Oklahoma Music Hall of Fame alongside other Red Dirt artists including The Great Divide and Jason Boland & The Stragglers. Ragweed also received the T3R Icon of the Year Award at the 15th Annual Texas Regional Radio Music Awards in March 2025.
Contemporary, friend and front man for The Great Divide, Mike McClure, will present the award to Canada at 6:45pm, which will be followed by a “Cody & Friends” set at 7pm and finally, a Family Jam with all musicians invited to stage at 7:30pm. The Award, named for Bob Childers’ song with the same name, is given by the Red Dirt Relief Fund in recognition of a musician who has made a notable impact on the Oklahoma Red Dirt music community. Canada joins a prestigious and beloved litany of Restless Spirit Award honorees: Jimmy LaFave (2017), Brandon Jenkins (2018), Randy Crouch (2019), Steve Ripley (2020), Jim Paul Blair (2021), Chad Sullins (2022), Jake Flint (2023) Monica Taylor (2024) and Don Morris (2025).
Jimmy LaFave Songwriting Contest Winner
At 4:15pm at the Grand Casino Stage at Eskimo Joe’s, the winner of the 2026 Jimmy LaFave Songwriting Contest will be presented a check for $750 and a free day of recording at The Church Studio in Tulsa. Three contest finalists are currently vying for the People’s Choice prize determined by online voting through March 29th. This year’s finalists include Micah Felts (Sand Springs), Gracie Sparks (Oklahoma City) and David Delgago “Neverdave” (Ardmore).
Venues & Festival Tickets
Will call, festival merchandise, a silent auction and vendors will be located at the main festival grounds at the Eskimo Joe’s Stage. A secondary ticket and merchandise area will be located near the shuttle stop on Washington St.
Festival venues include:
- Grand Casino Main Stage at Eskimo Joe’s (all ages, outdoor, 501 W. Elm St.)
- Busch Light Stage at The Wormy Dog (21+, 421 S. Washington St.)
- Suncruiser Stage at The Dirty Rooster (21+, 319 S. Washington St.)
- Salty Bronc (21+, 911 W. 5th Ave.)
- George’s Stables (21+, 502 W. Elm St.)
General Admission tickets good for entry to all festival venues Sunday are $35 advance, $40 day-of with a $10 discount for students and military members with ID. Reserved seating add-ons, Brunch and After Dark tickets range from $20-$150. Tickets and more info at https://www.reddirtrelieffund.org/gypsycafe/
The Causes
Proceeds benefit Oklahoma music creators in need through the festival’s organizer, Red Dirt Relief Fund, as well as other nonprofits serving the Stillwater community including Our Daily Bread, Cardinal’s Love for the Homeless and Friends of Sanborn Nature Camp.
Red Dirt Relief Fund was founded in 2012 using the ticket proceeds of the very first Gypsy Café festival held in Stillwater in 2011. Since then, the nonprofit has granted more than $1 million in emergency assistance to more than 800 music professionals in all genres and jobs statewide, including more than $300,000 to those facing venue closings and gig cancellations during the pandemic. This aid helps music people pay personal bills and expenses while they recover from medical conditions, accidents, mental health and rehabilitation and other unavoidable emergencies. The organization also connects Oklahoma music creators to affordable health insurance and other health and wellness services.
Bob Childers’ Gypsy Café is the organization’s largest annual fundraiser thanks to support from sponsors Grand Casino, Stillwater Medical Center, Cove Environmental, Oklahoma Film + Music Office, Tito’s, Suncruiser, Busch Light, Home2Suites, Kicker, Visit Stillwater, KOSU, Frank’s Food Shack and other community partners.
For more information, visit reddirtrelieffund.org or contact Katie Dale at 918-407-4599 or [email protected].
