The Kentucky Headhunters and Confederate Railroad book Hagerstown's Maryland Theatre
The Glasgow, Kentucky, band behind Pickin' on Nashville plays the 1915 theatre on Friday, February 26, 2027, with Confederate Railroad and Ray Scott.

Downtown Hagerstown has a 1915 vaudeville house that has outlived a near-fatal fire, and in February it gets a country-rock bill built for a room with that kind of history.
The Kentucky Headhunters play the Maryland Theatre on Friday, February 26, 2027, at 7 p.m., with Confederate Railroad and Ray Scott on the bill. Tickets are sold through Ticketmaster. The show was announced Oct. 26, and the theatre holds 1,279.
The Headhunters' roots go back to 1968 in Glasgow, Kentucky, when the core of the band was playing as Itchy Brother. The Kentucky Headhunters name came in 1986. Their road to a record deal is one of country's better underdog stories: a backer lent the band $4,500 to cut an eight-song demo, the demo made its way to Nashville, and Mercury Records signed them and released it, finished in studios in Bowling Green and Glasgow, as their 1989 debut, *Pickin' on Nashville*.
That record did what demos aren't supposed to do. It produced four Top 40 country singles, including a No. 8 cover of "Oh Lonesome Me," went double platinum and won the Grammy for Best Country Performance by a Duo or Group with Vocal. The band also won CMA Album of the Year and Vocal Group of the Year for 1990. Rolling Stone later described them as the Chris Stapleton of the 1990 CMAs: a hairy, loud, blues-soaked rock band that crashed country radio on its own terms.
A backer lent the band $4,500 to cut an eight-song demo. That demo became a double-platinum debut.
The room is a draw in its own right. The Maryland Theatre opened on May 10, 1915, as a vaudeville and silent-film house designed by Hagerstown's Harry E. Yessler with New York's Thomas W. Lamb. Opening night mixed live acts, including the Tiller Sisters and an acrobatic trio, with a film. The building was listed on the National Register of Historic Places in 1976, was nearly destroyed by fire in 1974, reopened in 1978, and a 2019 project restored it to its original 1915 footprint.
That makes a 7 p.m. start on a Friday an easy night out. Three acts means a full evening, so plan on being in your seat early rather than catching only the headliner.
There's something right about a band that started out in a small Kentucky town playing a century-old theatre in a small Maryland city. Bring someone who still has *Pickin' on Nashville* on cassette, and someone who has never heard it. Both will leave happy.
Sources: The Kentucky Headhunters — Wikipedia (en.wikipedia.org); The Kentucky Headhunters — Kentucky Music Hall of Fame (kentuckymusichalloffame.com); Keep On Rollin' — Phoenix New Times (phoenixnewtimes.com); How Kentucky Headhunters Were the Chris Stapleton of 1990 CMAs — Rolling Stone (rollingstone.com); Maryland Theatre (Hagerstown) — Wikipedia (en.wikipedia.org); History — The Maryland Theatre (mdtheatre.org); Maryland's National Register Properties — Maryland Historical Trust (apps.mht.maryland.gov); The Kentucky Headhunters at Maryland Theatre — JamBase (jambase.com); Tickets — Ticketmaster (ticketmaster.evyy.net)
Drafted with AI from the sources below and our show listings, then checked and approved by an On at 8 editor before publishing. Spot a mistake? Report an error.
- The Kentucky Headhunters — Wikipedia
- The Kentucky Headhunters — Kentucky Music Hall of Fame
- Keep On Rollin' — Phoenix New Times
- How Kentucky Headhunters Were the Chris Stapleton of 1990 CMAs — Rolling Stone
- Maryland Theatre (Hagerstown) — Wikipedia
- History — The Maryland Theatre
- Maryland's National Register Properties — Maryland Historical Trust
- The Kentucky Headhunters at Maryland Theatre — JamBase
- Tickets — Ticketmaster