“I was a young troubadour, when I rode in on a song.... And I'll be an old troubadour, when I'm gone,” sings George Strait in “Troubadour.”  

Troubadour were lyrical poets of the Middle Ages, and that definition still rings true for the troubadour of Strait’s song, songwriters Leslie Satcher and Monty Holmes.  

Taking inspiration from troubadours like Satcher, songwriter Jo Smith and event producer Cari Keppler joined together in 2023 to form Big Sky Troubadours, a Whitefish-based music production company. 

Klepper grew up on a cattle ranch in Shelby and her parents have had a home in Whitefish since 1970. Smith moved to Whitefish from Nashville about six years ago. 

Big Sky Troubadours is re-branding the Whitefish Songwriting Festival, which has taken place for the last three years, to Downtown in the Round this year.  

The songwriting festival takes place this weekend, Oct. 11 – 13.  

“I’m excited to have songwriters in all my favorite venues here simultaneously... we have solo shows all the time, but to multiply the energy is going to be super fun. Long live the songwriters,” said Smith.  

Klepper said that the new version of the event will allow more locals to shine and for visiting songwriters to better connect to the people and scenery of Flathead Valley.  

While the festival is their grand production, Big Sky Troubadours also hosts songwriters for Jo + Friends, supper and book clubs throughout the year.  

“They say the best gifts to give are the ones you yourself want. That sums up my personal inspiration for joining with Cari to create Big Sky Troubadours,” Smith said.  

Smith, who grew up on a farm in south Georgia, said her first public performance was when she was 3 years old.  

“I don’t really know anything else.” 

When she was 19, Smith said she put her “nose to the grindstone and decided to try and make a career of it.” 

She moved to Nashville and chose the writing path “with reason.” 

“At the time, American Idol and other talent shows were booming, and a lot of artists were encouraged to get success quickly that way. But I knew I was in a longer game... so I just started to play honky-tonk shows, try and get publishing deals while learning to truly write. 

“It’s ironic because at the time, Luke Bryan was about the only person I knew in town, and he encouraged me to pursue songwriting and to play my own songs, instead of being a hairbrush singer... and now he’s a TV show judge,” Smith joked.  

After feeling burnt out after 15 years in Nashville, Smith moved to Whitefish and said she “reconnected with what inspired me to make music my livelihood in the first place: God’s beautiful creation, family and audiences that listen for the love of it and without judgment.” 

“Songwriters are storytellers,” Klepper said. “Some are writers, some are performers, some are both. There’s magic in being in a room with people where there's greatness in what they’ve done, but they’re not famous,” Klepper said.  

As for organizing the festival drawing in national talent, Klepper said they have help with social media, “but mostly, it’s just Jo and I, until we can grow. But we have many volunteers; it’s a community-oriented event.” 

Shows this weekend will be held in four downtown Whitefish venues: Second Story at 101 Central, Remington Bar, Great Northern Bar & Grill, and Slow Burn Records. 

Each live show will feature two or three songwriters telling stories and strumming songs in creative and intimate ways. Special sessions include “The Night of No. Ones” and “Three Cords and the Truth.” For both Saturday and Sunday, Coffee & Conversations will start the morning, with shows throughout the day, and an open mic session that is free to the public to finish off the night.  

The lineup includes Nashville songsmiths Brice Long, Trannie Anderson, Josh Phillips, Marla Cannon-Goodman, Phillip White and Jo Smith. Collectively, they have written hundreds of songs for artists like Lainey Wilson, Luke Combs and Chris Stapleton.  

Participating local artists include Tom Catmull, Hannah King, Nick Spear, Miller Campbell, Kalyn Beasley, Abigayle Kompst, Rylee Mix and Tomara.

People can expect to make connections between the lyrics they sing and their true origins.  

For example, Josh Phillips, writer of “Dirt Cheap,” which just hit number one on the country charts, is about the memories and relationships built onto the land. The song’s performer, Cody Johnson, personally connects to the lyrics as a family man pouring effort into his land as a first-generation cattle farmer.  

For more information about Downtown and the Round and tickets, visit www.bigskytroubadours.com/downtownintheround.