By Matt Wickstrom
Aaron Raitiere performs at Sleeping In The Woods on May 17, 2025
For a moment I didn’t think it would happen. After the threat of severe storms wiped out Friday’s slate of music at Sleeping In The Woods and tornados swept through nearby Somerset and London later than night — killing more than 20 (and counting) — I full expected to wake up on Saturday to the news that the entire festival was a wash. Thank goodness I was wrong.
Despite the devastation so close by the festival went off — albeit a day late — without a hitch. Not even a symphony of cicadas, returning to the surface after 13 years underground, could dampen what’s quickly become my favorite musical gathering of the year. Nicholas Jamerson — already a Kentucky music legend in his own right — and his team have done a great job curating the event, which featured it’s most diverse palette of music yet in year three.
As always, Kentucky’s present and future were well represented with the likes of cello extraordinaire Ben Sollee, Nashville songwriter Aaron Raitiere, upstarts like John Thomas Moore, Lindsey Elam and Charlie Overman. However, folks from outside the Commonwealth like Pennsylvania’s Maya De Vitry, Virginia’s Cody Christian, Australia’s Tori Forsyth and Ohio’s Mo Reen did well to make their voices heard as well.
Nicholas Jamerson and Aaron Smith play along during Zach Martin’s kids’ set and drum circle at Sleeping In The Woods on May 17, 2025
In addition to the formidable songwriting present at the festival all weekend, another of my highlights at Sleeping In The Woods is always the amazing family atmosphere conjured up on the grounds of the Hidden Ridge Campground. From start to finish kids were frolicking all around the site, doing everything from blowing and popping bubbles to listening to the music — and sometimes even taking part in it themselves.
Such was the case Saturday afternoon when drummer Zach Martin led a kid’s inspired drum circle that — by my count — had well over two dozen miniature participants. After warming up the circle with some basic drumming exercises Martin eventually welcomed Nicholas Jamerson and fiddler Aaron Smith into the circle for an instrumental medley that saw several of the children get to stand up and play alongside them, surely creating core memories that will last — and potentially shape them into musicians — for years to come.
To commemorate the weekend that was I’ve highlighted my five favorite moments from the third iteration of Sleeping In The Woods below.
Emily Jamerson
Emily Jamerson was joined by her brother Nicholas for a performance of “Coal Camp Queen”
First to take the stage on Saturday (following a yoga session and songwriting workshop) was Emily Jamerson, someone who’s quickly become one of my favorite voices and writers in the Kentucky music scene despite not beginning to play out until recently.
From breaking down while singing about the dog she had to put down earlier this year to ruminating about not settling when it comes to finding love, Jamerson’s songs ooze with vulnerability and emotional depth that make it impossible to not stir up those same feelings within the listener (and if you don’t you might need to check your pulse).
While most of the set was performed solo, another highlight came near the end when she welcomed her brother Nicholas to the stage for a duet on “Coal Camp Queen,” a song written by Nicholas and their other brother Joseph about their grandmother after she passed away.
Maya De Vitry
After getting turned onto her music years ago while interviewing Michigan born, Nashville based singer Lindsay Lou for Bluegrass Unlimited I’ve been a fan of Maya De Vitry’s ever since, but Sleeping In The Woods was my first time actually getting to see her in person. Newsflash — she didn’t disappoint!
After opening with “Nothing Else Matters” — a tune that Lou cut on 2023’s Queen Of Time — De Vitry later dove into songs like her latest single “Flowers” as well as “Working Man,” an original that Nicholas Jamerson includes a version of on his forthcoming album The Narrow Way featuring West Virginia picker Tim O’Brien.
Aaron Raitiere
Another artist I’ve been a longtime fan of but finally saw live for the first time this past weekend was Aaron Raitiere. Despite the hit songs he’s written for the likes of Miranda Lambert, Ella Langley and Lainey Wilson I was expecting a lot of light-hearted gag songs in his set, but even I wasn’t prepared for the absolute musical comedy show he wound up delivering.
From his wooden flute opening to the one word song “Weeeeeeeeeeeeeeeeeeellllllll,” spoken word rallying call “Go Turtles!,” and straightforward hymns like “Chill Out, Drink a 7-Up, Eat A Moonpie And Quit Murdering People” he had the crowd rolling around laughing on the forest floor through the entirety of his set similar to what I’ve come to expect from the dry humor at an S.G. Goodman or John Craigie concert.
Later in the set Raitiere welcomed hometown hero and one of his biggest songwriting collaborators, Jon Decious to the stage. Together the two performed a handful of songs led by two bonafide truck tunes — the plot twist-heavy “Hit By A Truck” and “4X4XU,” the latter of which went on to be a number one song on country radio last year for Lainey Wilson.
Raitiere’s success — both in songwriting circles and on the stage Saturday night — are prime examples that the best way to succeed in life is by being 100% you every step of the way, no matter how weird things may get at times.
Lindsey Elam and Charlie Overman
Even with Lucas Wayne unable to attend after Friday night’s tornados impacted his family out west, Lindsey Elam and Charlie Overman delivered arguably the weekend’s most powerful songwriting rounds. The song swapping session was my first opportunity to catch the Ashand native Elam live, and she didn’t disappoint.
From songs calling out the United States’ current political climate (see above) to songs about love and showing personal restraint during times of strife, Elam put herself on notice as a Kentucky songwriter that demands your attention with her commanding voice and lyrics that contain 100% truth and 0% BS.
Elam’s songs were a stark contrast to those from Overman, which tended to be on the less serious side, almost like a Kentucky version of John Prine. Similar to Raitiere, Overman’s unassuming delivery and approach to songwriting is what makes him so great. His unwavering humility and lack of an ego help turn the characters and scenarios in his tunes from ordinary to extraordinary in a way that few others can match, making him a true Kentucky treasure that we’d be wise to cherish now before he’s off playing bigger stages elsewhere.
Ben Sollee
Speaking of playing bigger stages elsewhere, I can’t think of a bigger treat to cap off the epic weekend at Sleeping In The Woods than a solo set from Kentucky music legend, Ben Sollee.
Singlehandedly responsible for making the cello great again by introducing it to a new, younger audience of fans and showing how it’s much more than a classical instrument, Sollee showed off a bit of that magic Sunday afternoon with rootsy, pop-infused ballads like “Prettiest Tree On The Mountain” and “Pieces Of You” while his two children ran laps around the stage, bringing the festival’s family forward mission full circle.
