Bob Childers' Gypsy Cafe
May 5, 2024

2024 Gypsy Cafe  tickets now on sale!

Join us in Stillwater on Cinco de Mayo (May 5th) for Bob Childers’ Gypsy Cafe, Oklahoma’s largest homegrown songwriter festival! With five venues, 70+ artists and Bob’s “Mexican Morning” Brunch, the 13th annual musical extravaganza benefitting Oklahoma music creators in need will be an experience you don’t want to miss. Follow us on Facebook and Instagram for more details and lineup coming soon!

Want a chance to play Gypsy Cafe and win a $1000 cash prize? Unsigned Oklahoma-based songwriters of all genres are invited to enter one original song in the Jimmy LaFave Songwriting Contest by March 3rd. Free to apply HERE

Restless Spirit Award 2023: Jake Flint

At the Grand Casino Stage at Outlaws, the Restless Spirit Award honoring Jake Flint was presented to his widow, Brenda Flint, alongside his family. Later in the evening, the guitar painted above by artist, Nathan McCray, was sold in a live auction for $8,000 to support the Red Dirt Relief Fund. 

Flint was a red dirt songwriter who played regionally, recorded four albums throughout his career and was named “Breakout Artist of the Year” at the We Are Tulsa Music Awards in 2019. He was a longtime friend to many of the musicians on this year’s lineup and beyond, as well as a loyal supporter of the Red Dirt Relief Fund. Flint performed at Gypsy Café three times and produced livestreams of Red Dirt Relief Fund events and festivals during the pandemic when events could not be done in person. Flint tragically died in his sleep a few hours after his wedding to Brenda in November 2022.

The Restless Spirit Award is given by Red Dirt Relief Fund in recognition of a musician who has impacted the Oklahoma music community in a spirit akin to Bob Childers, a prolific songwriter and the so-called godfather of red dirt music. Previous honorees include Jimmy LaFave (2017), Brandon Jenkins (2018), Randy Crouch (2019), Steve Ripley (2020), Jim Paul Blair (2021) and Chad Sullins (2022).

A round of applause for our partners!

past Gypsy Cafe


Take a trip down memory lane and check out some of our past festivals and their highlights.

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