Gypsy Cafe Schedule, Restless Spirit Award & Jimmy LaFave Song Contest Winner Announced

Bob Childers’ Gypsy Café, Oklahoma’s largest homegrown songwriter festival, has released the schedule of 75 songwriters performing across five venues  on Sunday, May 7th in Stillwater, Okla. During the festival, Jake Flint will be honored posthumously with the Restless Spirit Award, and Brent Giddens will perform as the winner of the Jimmy LaFave Songwriting Contest.

Now in its twelfth year, the festival benefits Red Dirt Relief Fund, the nonprofit that provided aid to more than half the artists in the lineup during the pandemic, and more than $700,000 to  music professionals statewide over the past decade.

The Schedule

With the addition of three new venues this year, festival organizers created a grid to help attendees plan the best way to see 75 of Oklahoma’ best songwriters perform acoustic song swap sets. The festival is also providing a free shuttle that will run a loop around festival venues throughout the day. See the grid and purchase tickets at

Restless Spirit Award

At 5:40pm at the Grand Casino Stage at Outlaws, the Restless Spirit Award honoring Jake Flint will be presented to his widow, Brenda Flint, alongside his family. 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).

Jake Flint, Eliza Bee, Kierston White & Stoney LaRue performing at 2019 Gypsy Cafe.

Jimmy LaFave Songwriting Contest Winner

At 4:40pm at the Grand Casino Stage at Outlaws, Brent Giddens will be awarded a $600 cash prize along with the titles of overall contest winner and “People’s Choice” with his song, “Shades of Texas.” The song was selected out of 68 entries alongside finalists Nellie Clay and Joe Baxter. Giddens will perform the song following the presentation as part of his set with Mike McClure, Bryon White and Buffalo Rogers. Hear this year’s top three songs, get more contest information and view previous winners at

Venues & Festival Tickets

New to this year’s festival, the White Buffalo Brunch at Stonecloud Brewing includes a brunch buffet from Good Little Eater, two drink tickets from Stonecloud Brewing and a Red Dirt Rangers set of Bob Childers’ tunes with Randy Crouch, Cody Canada, Carter Sampson, Mike McClure and other guests from the festival lineup.  Tickets are limited and include GA admission to all festival venues.

Eskimo Joe’s Main Stage will include regional vendors and a silent auction of one-of-a-kind music experiences and memorabilia. Before the all-lineup family jam finale, there will be a live auction of a Gypsy Cafe guitar signed by the entire lineup and a live painting by Bobby Moore, a member of Tulsa-based band, The Brothers Moore, who is also playing the fest.

Festival venues include:

  • Eskimo Joe’s Main Stage (all ages, outdoor weather permitting, 501 W. Elm St.)
  • Grand Casino Stage at Outlaws (21+, 501 S. Washington St.)
  • Coors Light Stage at Salty Bronc (21+, 911 W. 5th Ave.)
  • George’s Stables (21+, 502 W. Elm St.)
  • White Buffalo Brunch at Stonecloud Taproom—SPECIAL TICKET REQUIRED (all ages, 917 S. Husband St.)

General Admission tickets good for entry to all festival venues (excluding Brunch) are $30 in advance at or day-of for $35 or $25 for students with ID.

 A limited number of tickets for the White Buffalo Brunch and Reserved Seating at the Eskimo Joe’s Main Stage range from $80-$150.

The festival will provide a free shuttle running a loop around the general admission venues from 1-8pm on May 7th.

The Cause

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 $700,000 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.

Now in its twelfth year, Bob Childers’ Gypsy Café is the organization’s largest annual fundraiser thanks to support from presenting sponsors Deep Eddy Vodka, Skrewball Peanut Butter Whiskey, Jose Cuervo Tequila, Jack Daniels, Grand Casino and many community partners.

For more information, visit or contact Katie Dale at 918-407-4599 or

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