Sleeping in the Woods Festival 2023 Review: Five Best Acts

Oftentimes first year festivals can be hit or miss, but the inaugural Sleeping in the Woods Songwriter Festival in Southeastern Kentucky was nothing short of a home run.

The small gathering of only a few hundred hosted some of Kentucky’s best songwriters alongside other rising stars like Bella White and Ben Danaher plus Nashville mainstays like Jim Lauderdale, the latter of whom led a funny and informative songwriting workshop on the gathering’s second day.

Storytelling in the form of song was front and center throughout the weekend in a profound manner that few festivals ever manage to establish, even after years in the game. Respectful and attentive crowds soaked it up throughout the two days, not once slowing down to let a Saturday morning rainstorm dampen their spirits.

Crowd participation was nothing short of euphoric at times, perhaps best illustrated during Katie Toupin’s Friday afternoon set which saw the audience singing along during her ‘Topo Chico Theme Song’ as well as ‘Sedona’, a 2x certified platinum single she helped to write in the mid-2010s for her former band, Houndmouth.

Even when the stages quietened down, the music never died. Campfire picking kept the party going into the wee hours of the morning on both nights thanks to folks like Wesley and Aaron Smith, Lucas Wayne, T.J. Kennedy and Arthur Hancock refusing to let the good times fade away. It all cultivated a beautiful environment for community and creative fellowship that will only continue to blossom in the years ahead.

With every performer bringing their ‘A’ game it was like pulling teeth figuring out only five to feature in this review. From songwriter rounds to workshops, solo and full band sets, every artist put their best foot forward, helping to elevate the entire weekend and make it one that those in attendance won’t soon forget.

This is Holler’s guide to the five best things we saw at the inaugural Sleeping in the Woods Songwriter Festival.

Delivering a mix of Appalachian folk n’ soul in an exhilarating one-man band format was Scott T. Smith. The Louisville native had the audience eating out of the palm of his hands throughout the recital of originals like ‘Love Them As They Are’ and ‘Honeysuckle’ thanks to his profound delivery and extensive vocal range that presented a fully-fleshed out sound rarely achieved by solo troubadours. Despite the rarity of the circumstance, Smith’s ease of achieving it appeared almost effortless, only driving home his artistic prowess that much more.

Performing as a trio backed by husband Adam Chaffins and Aaron Smith, Brit Taylor’s star shined bright during a side stage set that included polished and heartfelt tales like ‘Cabin in the Woods’, ‘Rich Little Girls’ and ‘Wagon’. Breaking up her own hits were originals from Chaffins, including ‘Kentucky Girl’ and a cover of Linda Rondstadt’s ‘When Will I Be Loved’ as day turned to night.

One of several songwriter rounds on the weekend, the grouping of Jordan Allen, Emily Jamerson and Don Rogers proved to be a formidable one of epic song swapping and captivating storytelling. Among the highlights were Allen’s rendition of ‘Been So Long’ — a tear-jerking tune penned for his father that book ends his forthcoming album The Makings of a Man — along with the soul-searching ‘Out of Luck’ from Jamerson and the tongue-in-cheek ‘He Split the First Church of God’ from Rogers, an original previously recorded by fellow Kentucky mainstays The Local Honeys.

The next Kentucky artist deserving of a seismic breakout, festival host Nicholas Jamerson and his band The Morning Jays delivered (and then some) with a three hour set. The mammoth headlining performance included a full run-through of his new album Peace Mountain followed by an assortment of other hits like ‘Linda James’, ‘It’s a Long Way to Wheelwright’, ‘Hindman’, ‘Brother Rabbit’, ‘Floyd County All-Star’ and a show closing ‘Sleepin’ in the Woods’, further cementing his legacy as one of the state’s most prolific songwriters.

Another of Kentucky’s great musical minds is Arthur Hancock, who had the tall task of following Jamerson for a late-night bluegrass set with his all-star collective Hancock & [Chris] Shouse. The 22-song showing saw a who’s who of festival performers join the troupe on stage for surprise sit-ins. Jim Lauderdale took on Flatt & Scruggs’ ‘Doin’ My Time, Spooky Fox joined for Bob Dylan’s ‘All Along the Watchtower’ and Jamerson performed once more with Jim Croce’s ‘Bad, Bad Leroy Brown’. Also mixed in for good measure was a blistering cover of Bruce Springsteen’s ‘Atlantic City’ and Hancock original ‘Take Me Back to the Country’ that shined a light on escaping the city for a weekend in the woods, a perfect fit for the remote musical gathering in Monticello.

Photography by Sarah Cahill / Tom Wickstrom