DISPATCH: An Intimate and Essential Kentucky Festival, Sleeping In The Woods

There’s something in the water in Kentucky that’s conducive to making great songwriters, and the second annual Sleeping In The Woods Festival — held May 17-19 in Monticello — was no exception.

Hosted by artist and songwriter Nicholas Jamerson, the gathering has quickly become a can’t-miss attraction featuring a mix of the Commonwealth’s most revered songwriters, as well as the ones they’ll eventually be handing the reins off to. The setting of Hidden Ridge camping — a birch tree-covered campground nestled along Lake Cumberland — further elevated its intimate feeling (in addition to providing a canopy of shade during a deluge of rain Friday).

However, despite Mother Nature’s best efforts on day one, the few hundred in attendance didn’t have their spirits dampened by the soggy forecast, instead filling out a massive tent by the festival’s second stage for a songwriter round to open things up. Featuring Ryan Anderson of Louisville rock band Bendigo Fletcher alongside Jamerson, in a last minute change of plans, the two opted to debut entirely new and unrecorded music during the hour-long round, further putting a microscope on their superb songwriting, the stories behind them, and the creative process at an event built for exactly that. Outside of rain pattering on the tent above, you could hear a pin drop. Even though fans weren’t familiar with these songs, it was obvious they were captivated by the occasion, a sign of the duo’s songwriting prowess and power of getting caught up in the moment.

Nicholas Jamerson and Ryan Anderson (Bendigo Fletcher) open Sleeping In The Woods festival with a songwriter round.

“Getting to play all new songs with Ryan Anderson felt like the perfect way to set the tone for the festival,” Jamerson tells BGS. “I’ve admired him so getting to share that space meant a lot.”

Following the round of new material was one of the festival’s few non-Kentucky acts, Cristina Vane. As a result I found myself talking with countless folks as she set up about what to expect from the electrifying slide guitar and banjo picker, but even my best of introductions couldn’t have prepared them for the show she gave them.

Working as a trio with drums and bass guitar, Vane tore through originals like “Blueberry Hill” and “Small Town Nashville Blues” alongside new songs like “You Ain’t Special” and sweltering covers like James McMurtry’s “Choctaw Bingo.” Through it all, she had the crowd at her will, seemingly unaware of the rain falling around them, including myself.

Cristina Vane performs at Sleeping In The Woods.

Although I’ve seen Vane perform several times, each occasion always feels like a first due to the versatility of her band setups. I’ve seen her play solo, with a full electric band, a full bluegrass band, and now as an electric three-piece; each show feels so different. Her songwriting is built for a festival like Sleeping In The Woods, but how she’s able to plug and play, presenting her music in many different ways is what truly sets her apart. Fans on Friday seemed to agree, giving Vane a ferocious standing ovation at her set’s conclusion, something that even she didn’t seem to expect.

“It was cool seeing people react to acts they hadn’t seen,” shares Jamerson. “I felt like Cristina Vane, The Dick and Tammy Show (Justin Clyde Williams and Tyler Hatley), and Josh Slone all made really huge impressions on people.”

Another out-of-state act integral to the weekend was Rachel Baiman. The Nashville-based multi-instrumentalist was everywhere over the three-day event, starting with a songwriter workshop she led to begin Saturday’s musical menu. Attended by around 50 under the tent that Cristina Vane rocked out the night prior, the croissant-fueled workshop saw Baiman working with fellow songwriters and aspiring ones alike to take internal conflicts and turn them into external ones via song.

This drew a mix of interesting inspiration from the heavy — a man trying to fit in with his different groups of friends and a mom and pop trying everything to keep their small business afloat — to tongue-in-cheek ones, like a prompt about how losing your Chapstick makes you feel like an inadequate lover.

“The songwriting workshop was both a complete joy and completely terrifying,” recalls Baiman. “Trying to ‘teach’ songwriting to some of my favorite songwriters felt a little crazy, but I think it really contributed to the class, because we could hear ideas from newcomers and seasoned professionals side by side.”

Rachel Baiman leads a songwriting workshop on day 2 of Sleeping In The Woods festival.

Outside of the workshop, Baiman also led a songwriter round of her own on Sunday afternoon that she used to showcase recent co-writes with Pony Bradshaw (“Equine Elvis”), Caroline Spence (“Throw Away The Moon”), and Jamerson, who joined her for a performance of their song, “The Vine That Ate The South,” due out next month. Additionally, she took to the stage with Leah Blevins, an Eastern Kentucky singer by way of Nashville, prior to Sunday’s round, fiddling with the Sandy Hook native on a selection of songs including the nostalgic “First Time Feeling.”

The set was a grounding one for Blevins, who expressed a longing to return home from Nashville in recent months even as she’s hit a breakthrough, signing a publishing and management deal with Major Bob Music in April. She expects to begin recording a new album soon.

“Any opportunity to be back home in Kentucky is a true sense of comfort,” says Blevins. “There are so many unbelievably talented artists there and this weekend was a true representation of that. It’s inspiring and always humbling to share the stage with folks that you genuinely respect like Nicholas. He’s always made me feel welcomed and his kindness alone is influential on a human level.”

Other Kentucky luminaries that stood out included Somerset’s Cody Lee Meece, brothers Wes and Aaron Smith — who were joined by Anderson on synth for an intriguing acousti-tronic sound — along with Ryan Allen & Maggie Noëlle’s stripped down versions of songs from their band, Magnolia Boulevard, and a Saturday evening round featuring three of the state’s stars of tomorrow: Salyersville native Zoe Howard, Hindman’s Josh Slone, and Central Kentucky’s Ireland Owens.

But it was Hunter Flynn, one of the state’s other promising young talents, that garnered the most attention. A local boy from just up the road in Somerset, Flynn’s Sunday afternoon set showcased the singer’s sensational songwriting and holler yell on cuts like “Spanish Street Signs” and “Fucked Up Brain” that have earned him recent gigs on the road with Zach Top and Ian Munsick, among others.

Hunter Flynn performs Sunday afternoon at Sleeping In The Woods festival.

In a pay-it-forward fashion similar to how Jamerson is platforming new artists with the festival, Flynn — who won a recording package from festival sponsor Jamm Nation during the event — plans to serve up his studio time to young artists in need on a collaborative EP that Jamerson will produce. According to Flynn, he wouldn’t be where he is today without Jamerson’s music and guidance.

“Before I knew Childers, before I knew Sturgill, before I knew Stapleton; I knew Nicholas Jamerson,” explains Flynn. “He might not have been the first to do it, but he was the first person that I knew from the Appalachian region that was writing songs and playing them for a living. Now I don’t know a single singer/songwriter from this region who doesn’t cover at least one of his songs. He could win six Grammys next year and it wouldn’t be as much recognition as he deserves.”

A more seasoned Kentucky artist that also turned heads was Henry County’s Joe Clark, who pulled back the curtain on songs typically backed by his country rock band, The Peacemakers, that touch on everything from drug addiction to the love he has for his father. Clark was hard to miss all weekend due to his towering presence, but heartfelt songs like “Wishin’ Well” and “Battlefield” showed a soft side to counter his hard exterior, one of the many things a powerful song can do.

Joe Clark takes the stage at Sleeping In The Woods festival.

“Music is my therapist. Along with my children and family it’s kept me sober and alive for years,” confides Clark. “I owe my life to songwriting. It is a power greater than me and I’m honored to put pen to paper each time a lyric comes to me. My biggest hope is to be able to take my real life experience and translate it through song in a way that someone else can take it and make it theirs and use it in a healing way for themselves. Music is medicine, and I believe everyone needs a daily dose to stay healthy.”

Closing out Sleeping In The Woods was one of the most iconic and influential Kentucky songwriters ever – Darrell Scott. For nearly two hours on Sunday afternoon the trailblazer showed off his fiery picking skills on iconic songs like “Never Leave Harlan Alive” and “It’s A Great Day To Be Alive,” giving all of the artists and fans in attendance something to look up to and aspire to in the process. The performance also left many in the audience visibly emotional including Jamerson, who could be seen tearing up throughout it.

“Having Darrell there really meant a lot,” reflects Jamerson. “It felt like we had the full spectrum of musicians, from green, next generation, seasoned vets and a master in Darrell. We are hoping to expose the youngins to a sustainable path in this industry, so having someone like Darrell was really validating for me.”

Darrell Scott headlines Kentucky’s Sleeping In The Woods festival.

From vets like Darrell Scott to youngins like Josh Slone, Zoe Howard, and Hunter Flynn, and present day stars like Nicholas Jamerson, Sleeping In The Woods was proof of many things — that Kentucky music is in as good a place it’s ever been, that smaller, niche festivals do have a place in today’s music landscape, and that great songwriting will never go out of style.

“It feels like the best way to kick off the year,” describes Jamerson, who’d been laying low since his two-night Hollerday Gitdown in December. “It’s such a great group of people that makes it all happen. It’s also really grounding, inspiring and a nice reminder of the community of people that I’m a part of, which is uplifting and gives me life going into the busy season.”

All photos by Joe Wilkins, courtesy of Sleeping In The Woods festival.