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Kentucky Music Round-Up: May 17-23, 2025

Published May 23, 2025

After over a decade of performing Harlan, Ky.’s Dakota Saylor today dropped his debut single, “Letterbomb.” The twangy country and bluegrass tune paints a picture of small town melancholy and places and people that are no longer filling your cup, a fary cry from the alternative rock scene he first began making waves in during the mid 2010’s.

Resurrecting a Dream: Dakota Saylor’s "Letterbomb" is set to break the silence…with a bang

Published May 22, 2025

Harlan, Kentucky’s Dakota Saylor once embarked on quite the climb up the Appalachian music scene, beginning with his emergence from the alternative rock scene a decade ago. It was deep within the sounds of Appalachia that he found his true voice and began to hone his craft, paying his dues in the local Harlan scene and beyond as he performed his brand of tunes–even playing a coveted show on the regionally-revered Red Barn Radio. Looking back, as his musical orbit began to transcend its local arc, it seemed as if his star was forever set to shine bright--but then life did what life often does, coming around to dull it just a bit with the descent of the COVID-19 pandemic. Music as we once knew it crashed and burned and changed for everyone involved, from the homegrown songwriters to the millionaire megastars. However, we’ve found that when music flows through every atom of your celestial body, the innate need to create never leaves.

Premiere- Dakota Saylor: Letterbomb

Published May 21, 2025

In an easy telephone interview that quickly relaxed into more of a catch-up with an old friend (whom I’ve never met), I had a diverse chat with Dakota about everything from video games to rural healthcare. We delved into Old West history, deep, dark musical secrets, and even contemplated how sometimes the math just doesn’t math. Saylor (pronounced like “sailor”) is practically still a newlywed and has a toddler at home. He has a supportive family and a great job, and a new single dropping May 23 - everything to be happy and excited about - but still likes the sad stuff best.

Timing is Everything: Dakota Saylor’s Journey to His Debut Single ‘Letterbomb’

Published May 16, 2025

It was 2016, somewhere pushed back in a holler of Evarts, Kentucky. It was a Friday night. I sat in a one-room workshop with cinder block walls and a concrete floor — our makeshift practice space. The walls were lined with shelves cluttered with tools, and the floor was covered by an area rug scattered with guitars, amps, microphones, a bass, and a drum set. This was a typical weekend for me during my senior year of high school.

That summer, my friends and I had started a band. Among them were Brian Seiber (guitar), Parker Eads (drums), Jake Bush (bass), Dakota Saylor (vocals and guitar), and myself (vocals). That night was the first time I met Dakota.

Jeep Fest and Mountain Market return

Published April 16, 2025

“Saturday’s live entertainment features a roster of musicians featuring many local favorites as well as regional acts. The Turner Family Revival kicks the show into gear at noon, with Shyla Raleigh taking over the stage at 1 p.m. Laci Deaton will be on stage at 2 p.m. to entertain the crowd. At 3 p.m., the music breaks for the Cornhole Tournament to take center stage. Dakota Saylor brings the music back to the spotlight at 4 p.m., with regional favorites The Creekers headlining the musical entertainment for the day.”

Christmas concert set for Benham

Published Nov. 20, 2024

“The Betty Howard Coal Miner’s Memorial Theater in Benham will be the location for a night of jazzy traditional Christmas music. The show will start at 7 p.m. on Saturday, Nov. 30.|The concert will feature an array of local musicians including Justin Taylor, Shyla Raleigh, Dakota Saylor, Greg Hollins, Ann Schertz, Jordan Patel, and more.”

Jeep Fest returns for fall installment

Published Oct. 7, 2024

“…the event will feature a full lineup of music beginning at noon on Saturday. Live performances will be provided by local favorites The Kudzu Killers, Cody Howard, The Tripps, and Dakota Saylor.”

MAMAW Fest comes to Harlan

Published Jul. 23, 2024

“MAMAW Fest will include musical performances by Tiffany Williams, A.P. Harbor, Randy Wilson, Mountain Laurels, Red Fox Playa, Cara Coppola, Dru the Drifter, Slut Pill, Geonovah, Bek & The Starlite Review, Jeremy Short, Ben Fugate & The Burning Trash Band, Dakota Saylor, and Wayne Graham. Headliners The Local Honeys will take the stage between 4 p.m. and 5 p.m.”