KENTUCKY ROUND-UP: Oct. 18-24, 2025
New music, festival announcements, the return of John Hartford Days, and more!
Welcome back to Wick’s Picks! Below you’ll find a recap of new music and other headlines from the past week of Kentucky music. Listen to a year-long playlist of all the songs featured in these round-ups on Apple Music.
New Music
Kristofer Lee Bentley" - “Dunkirk Song“
On the penultimate track from his album The Protectors II out last week, Prestonsburg native Kristofer Lee Bentley about making the best of every moment you have with those you love. The song seems to be inspired by time spent inside this past winter and spring as everything from flooding to tornadoes swept through the Commonwealth, giving the tune an endearing sense of recency and perseverance.
Jory Bowling - “Home“
From his new album Of Water And Stone out last week, Jory Bowling sings about finding home not in a specific place, but rather a person that puts your heart and mind at ease and brings out the best of you, and vice versa.
Dylan Gossett - “Back 40” (feat. Ole 60)
Newly included in today’s release of Westward (Deluxe Edition), Texas singer-songwriter Dylan Gossett enlists Western Kentucky country rockers Ole 60 for his song “Back 40” — a tale about longing for a return to the youthful days of living free when they could just kick back in sprawling country fields with their friends without a worry in the world.
Abby Hamilton - “Fried Green Tomatoes”
Back with her second single drop in as many months, Abby Hamilton gives voice to her inner thoughts about relationships and her own avoidant attachment style on “Fried Green Tomatoes.” It’s a somber, heartfelt reminder to always love yourself and leave oneself open to receiving love because you never know who or where it may come from.
Adam Mac - “The Outside“ (feat. Chris Housman)
Queer, Kentucky born singer Adam Mac explores his struggle finding a seat at the table in country music on “The Outside.” The cut from his new album Southern Spectacle also features fellow queer country singer Chris Housman as it combines traditional country sounds with mode modern and poppy hooks.
Chace Saunders - “Bluegrass State”
Kentucky born, Nashville based singer Chace Saunders reminisces about his favorite Commonwealth memories as a coping mechanism for missing the place that raised him and counting down the days to returning on the certified banger “Bluegrass State.”
DeBraun Thomas - “Bourbon Tears” (Live)
To celebrate the 10 year anniversary of his album All My Colors Are Blind, rock n’soul singer DeBraun Thomas has dropped a live version of one of the songs from the record, “Bourbon Tears.” The song was recorded at the now-defunct music club Cosmic Charlie’s on June 18, 2016 — Thomas’ first concert after recovering from a broken hand that happened just after the album’s initial release the fall prior.
Benjamin Tod - “My Pride”
Feelings of regret boil to the surface on Benjamin Tod’s latest single, “My Pride.” On it the Western Kentucky singer combines themes of both empathy and accountability to examine how not only him, but all of us, could do better at considering other’s feelings and circumstances and how our own actions may impact them.
Other News & Notes
Candi Jenkins on Monday shared the music video for her latest single, “Hello June,” which first released earlier in the month.
After not dropping it’s 2025 lineup until January, Lexington’s Railbird Festival on Oct. 20 unveiled its full 2026 lineup coming to The Red Mile June 6 and 7. Performers include The Lumineers, Tyler Childers, Zach Top, Ella Langley, Stephen Wilson Jr. Margo Price and Nicholas Jamerson & The Morning Jays, among others.
Former Grand Ole Opry and Hee Haw star, “Grandpa” Jones, was posthumously recognized by the Kentucky Music Hall of Fame & Museum on Oct. 20, 112 years to the day after his birth in Niagara, Ky. Also celebrating a birthday this week was Kentucky born country crooner Dwight Yoakam, who turned 69 on Oct. 23.
Greenup County’s Jayce Turley is among the performers revealed on the initial lineup for the 16th iteration of Rooster Walk Music Festival coming to Pop’s Farm in Martinsville, Va. May 21-24, 2026. Other acts announced include Daniel Donato’s Cosmic Country, Mountain Grass Unit, Yarn, and Kindred Valley.
The Bluegrass Music Hall of Fame in Owensboro has announced a reprisal of it’s John Hartford Days celebration, which will return to the space with music from the Tim O’Brien Band, Robbie Fulks, and The Wildmans on Jan. 31, 2026.
New Bylines
“John’s ancestral home is in Kentucky and Muhlenberg County, so it only felt right to partner with a distillery from there. The first bourbon was so sought after that we thought it’d be fun to do again, especially with this being the last year of (the event) ‘You Got Gold.’” — the Hello In There Foundation’s Celine Thackston tells me about the origins of it’s bourbon collaboration with Muhlenberg County based The Bard Distillery for the Lexington Herald-Leader.
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Wick’s Picks Podcast
Stay tuned to my social media pages for announcements about our next guest in the coming days. The episode will air via 96.1 Hound FM, The Hound mobile app and HoundFM.com on Oct. 29 at 8 p.m. ET.