Who We Are

Since The Woodsheep’s inception in the summer of 2015, Andrew Preston’s songwriting – experimental, but rooted in the deepest wellsprings of traditional folk music – and their quirky live shows have become among the most recognizable mainstays of central Appalachia’s burgeoning indie scene. Among their hallmarks: soaring harmonies, offbeat instrumentation, literarily dense lyrics steeped in folk storytelling tradition, all balanced by a healthy penchant for the absurd.

The Woodsheep is the name given to the music of founder/producer/singer-songwriter/multi-instrumentalist Andrew Preston, who has been developing his style of deeply personal, narrative-driven lyrics and musically dynamic arrangements since his early schooldays. Inspired heavily by 2000's indie pop theatrics like those of The Hush Sound, KT Tunstall, and The Decemberists, as well as the intimate lyricism of John Prine, Stephin Merrit, and Regina Spektor, he became a musician organically, teaching himself to play several instruments and to record songs in his grandmother’s apartment. His career burst forth suddenly, when shortly before The Woodsheep’s founding, Preston was featured in the International Bluegrass Music Association’s Songwriter Showcase for his song “The Mountain Wayfarers”.

A collective of fellow musicians forge the Woodsheep’s theatrical sound in the studio and at live performances. Melissa Caskey provides a sassy-sweet vocal and Julie London inspired bass for the majority of Woodsheepery, while drummer Matt Holleran highlights the band’s characteristic pop-punk undertones. Wyatt Smith, the most recent addition to the band, joins Andrew in completing their Simon and Garfunkel-inspired harmonies for albums and occasional live shows.

In May 2015, The Woodsheep released their debut record Watching Mars, before embarking on a year-long American tour in support of the album. Since their inaugural Appalachian tour in 2015, they have also performed abroad in China in 2017 and again 2018, and most recently in the UK and Ireland. 2018 also saw the release of their sophomore album Sleeping Under Stars, along with an expanded pan-American tour which included the Sidewalk Café in New York City, a Mecca of indie and anti-folk artists who had long inspired the Woodsheep’s signature ‘genre hopscotch’. After over 600 shows throughout the United States and 3 other countries in only 3 years, The Woodsheep have released an EP, Numbers On Lemons to showcase their shifting sound. To bid farewell and pay tribute to their beginnings in folk music in favor of Andrew's indie productions, 2019 saw the release of a large concept album featuring 26 traditional Appalachian songs. The album, Old Time Pigeon, showcase Preston, Caskey, Holleran, and Smith on lead vocals and various folk instruments, and introduces vocalist Mary Morris to the mix.

From their first gigs in small Kentucky dives to international stadium shows, The Woodsheep have built a committed fanbase and reputation among venues through meticulous work and consistent touring. Even more than commercial success, Preston wishes for The Woodsheep to remain, as they have been since their earliest days, a staple of eastern Kentucky’s small-town communities.

The sound from the mountains of Appalachia has long been swelling at its banks, on the verge of spilling over the confines of folk and electronic music convention. The Woodsheep aim to highlight the diversity, creativity, and storytelling that abound their eastern Kentucky home by shoring up their own roots.

Meet The Band


Andrew Preston

-guitar, piano, ukulele, banjo, vocals

Melissa Caskey

-bass, autoharp, guitar, vocals

Matt Holleran

-drums, guitar, vocals