Sleeping in the Woods Festival 2023 Preview: Five Acts to See

From the hills and hollers of the Hidden Ridge Campground to the banks of Lake Cumberland, music will be echoing throughout this coming weekend when the inaugural Sleeping in the Woods Songwriter Festival rolls into the town of Monticello, south-central Kentucky.

Hosted by Prestonsburg-based songsmith Nicholas Jamerson, the intimate gathering - named after one of his most popular songs - will welcome top shelf songwriters from Kentucky, Nashville and beyond with the likes of Jim Lauderdale, Bella White, Lucas Wayne and Rachel Baiman all scheduled to perform.

The event will also serve as a de facto album release celebration for Jamerson, who will release his album Peace Mountain featuring Charles Wesley Godwin, Magnolia Boulevard and others on May 19.

Although it’ll be the festival’s first go-around, it’s far from the first gathering that Jamerson has curated. Also a member of country duo Sundy Best, he and bandmate Kristofer Bentley have organized the Kinfolk Reunion in their hometown the past three springs, in turn providing a blueprint for how Sleeping in the Woods will operate.

Part of that includes serving up other recreational activities, which the sprawling 53-acre campground has in droves with easy access to Lake Cumberland for swimming, fishing and boating along with disc golf baskets, hiking trails and more.

Music will be the main dish throughout the weekend, though, with everything from songwriter rounds to workshops and traditional sets taking center stage.

With everything on offer, we’re certain there won’t be much sleeping in the woods this weekend. To accommodate, we’ve gathered the five performances we’re most looking forward to at Kentucky’s newest music festival.

This is Holler's guide to the Best Things to See at Sleeping in the Woods 2023.

Based in Illinois, Lucas Wayne has found a second home in Kentucky in recent years thanks to his down-to-earth demeanor and gripping songwriting that will have you laughing one minute and crying a river the next. Need proof? Give a listen to his song 'No One Turns Me On', a tearjerker he wrote for his grandfather (who’s since passed on) from the perspective of his tableside lamp that offers astute observations of their time together and his deteriorating health.

A longtime bassist for Jamerson’s backing band The Morning Jays, Jordan Allen has also carved out his own space in Kentucky’s burgeoning music scene with his blend of Appalachian country, southern rock and soul. The London, KY native - who possesses one of the region’s most crisp and well-rounded voices - will be mixing songs old and new during a songwriter round with Don Rogers and Emily Jamerson as he closes in on the release of his second full-length album, The Makings of a Man, on June 16.

Currently one of the most sought after artists in bluegrass and folk music following last month’s release of Among Other Things, Calgary native Bella White will wow the Sleeping in the Woods crowd with her soothing vocals that feel more like they belong in 1963 than 2023. Thankfully for us, she’s thriving in the here and now with her earnest storytelling and a sound similar to fellow mountain music matriarchs Loretta Lynn and Patsy Cline.

Even though she’s done session and side-person work with the likes of Kacey Musgraves and Molly Tuttle, the true magic of prolific picker Rachel Baiman lies in her own songs, heavily steeped in the folk tradition. On her latest album Common Nation of Sorrow she tackles everything from socialism to mental health, moral debt and more, painting a full-scale mosaic of her traditional leaning influences and flexing her songwriting muscles in the process.

If you’ve earned the approval of Sturgill Simpson, you’re doing something right. Such is the case for Nashville-by-way-of-Eastern Kentucky artist Brit Taylor, who’s latest album Kentucky Blue was co-produced by Simpson and music city mainstay Dave Ferguson. With a commercial appeal and drive to write and sing her songs on her own terms, Taylor is not only a can’t miss artist at Sleeping in the Woods, but one of the top rising acts to keep your eyes (and ears) on in country music, period.

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