The Festival Jamboree

Rearranging the cultural landscape, one festival at a time

Inaugurating a new music festival in what feels like a saturated environment can be a leap of faith. For Dan and Amy Sheehan, veterans of the Northern California festival circuit, the opportunity to spread the joy of music and give a platform to artists trying to reach new audiences was worth it. Last year’s Rebels & Renegades Festival in Monterey far exceeded their expectations.

The event drew roughly 5,000 people both days, leading them to add a third day this year, which will take place Oct. 6-8 and include performances from Turnpike Troubadours, Charley Crockett, Sierra Ferrell and others.

This year’s expansion will also include the most iconic landmark of its host site, the Monterey County Fairgrounds — the enclosed stage previously used for the Monterey Pop Festival in 1967, which featured iconic performances by Jimi Hendrix, The Who, Janis Joplin and more.

“One of the biggest takeaways for us last year was how much appreciation the artists had for the thoughtfulness of how we went about it,” says co-founder Dan Sheehan. “A big reason for that is the home field advantage we have from doing other events on the grounds with the same crew. We got so many compliments that last year didn’t feel like a first-year festival, which is exactly what you hope for when starting something new.”

Regionally based music festivals like Rebels & Renegades are springing up everywhere, augmenting a circuit of more established ones which together are helping propel an independent country music scene that is currently rearranging the cultural landscape.

Another relatively new festival building a tight knit community on the foundation of showcasing regional talent is Laurel Cove Music Festival. Located in the southeast Kentucky hamlet of Pineville and started in 2019, the festival has been a springboard for some of Appalachia’s best songwriters in recent years, including Charles Wesley Godwin, Morgan Wade, Sierra Ferrell, Cole Chaney, 49 Winchester, S.G. Goodman and Kelsey Waldon. Held in an intimate amphitheater surrounded by towering trees and rock faces on all sides, the festival site at Pine Mountain —Kentucky’s first state park — is commonly referred to as “Kentucky’s Red Rocks”, for its combination of picturesque views and superb music.

“There’s such a hotbed of talent from here,” says festival organizer Jon Grace. “The artists we book all come back to being fans of the music ourselves. Nothing excites us, or our fans, more than discovering a new artist and seeing them up close like they can here. It’s a completely different experience seeing them perform from 20 feet away compared to on a big screen from 500 yards away at some of these bigger festivals.

While newer gatherings like Rebels and Laurel Cove are making waves, there’s also a handful of already established festivals that have found stability and success in their events spanning back decades. One such event is Pickathon, a family-friendly and eco-conscious gathering held at Pendarvis Farm outside of Portland, Oregon since 1999. Earlier this month the festival wrapped up it’s 24th edition with a diverse range of music that included Watchhouse, Madison Cunningham, Nick Shoulders and Emily Nenni.

“That was the best Pickathon ever!” says festival founder Zale Schoenborn. “Our reimagining of the festival fully came together and Pendarvis Farm became a total immersive experience that was much bigger than the sum of its parts. Festivals like Pickathon are rare in the world and to see so many people joined together in harmony — dancing, singing, wandering, rebuilding and exploring was truly a marvelous thing.”

Over a decade older than Pickathon and located nearly 3,000 miles away is Merlefest. Located in Wilkesboro, North Carolina, the festival began in 1988 as a one-off concert from Doc Watson. The goal was to raise funds for a new Garden of the Senses on the campus of Wilkes Community College that has since blossomed into one of western North Carolina’s most prominent annual events. Based on Watson’s own style of “traditional plus” music, Merlefest implements an array of sounds into its lineup including bluegrass, country, rock, blues, soul and more.

It’s also continued to be a force of positivity in the community nearly four decades from its start, having raised over $19 million in funds for the community college, including $476,000 in 2023. The even has also become a critical fundraiser for over 60 community and civic associations that volunteer at it every year doing everything from cooking to shuttling patrons. In total, Festival Director Wesley Whitson estimates that 2,700 volunteers work year round to produce Merlefest, proving that it indeed takes a village to produce an event of its magnitude.

“We have to give credit to all of the organizers back in the day with the foundation they built,” says Whitson. “They put this thing together with the core values of being community-oriented and promoting volunteerism from the very start. Our thought is that if it ain’t broke, don’t fix it. It’s pretty cool that so many years after Doc’s passing that Merlefest is still out in the world doing good for folks and carrying their legacy on.”

While Merlefest has always been on the campus of Wilkes Community College another similarly aged event has found an equal amount of success despite having called multiple places home over the years. Founded in Round Rock, Texas in 1987, the Old Settlers Music Festival has been making the Austin area weird long before the growing city adopted the moniker. In the years since the gathering has moved to Dripping Springs, Driftwood and now Dale, its home since 2018 on an expansive 142-acre property. Its new space also marks the first time the festival has owned its own grounds rather than renting one out, giving them more flexibility to curate the festival to their liking than ever before.

“It’s very cool to still be around and have that history of being a part of the old Austin,” says Executive Director Talia Bryce. “I think that’s what really attracts a lot of people to us. Folks often describe Old Settlers as the friendliest festival they’ve been to. We try to put a lot of attention into cultivating a lovely vibe while we’re out there, and it seems to be paying off.”

Events like DelFest in Maryland, Under The Big Sky in Montana, the Braun Brothers Reunion in Idaho, the Suwannee Spring Reunion and Fall Revival in Florida and Jackalope Jamboree in Oregon are all part of the new circuit, each one making a critical contribution to this music scene, helping artists to find audiences and cultivating a sense of community for their fans.

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