Featured in the 2015 International Bluegrass Music Association
World of Bluegrass Songwriter Showcase

"'Simplicity,' as defined by The Woodsheep, is not a lack of sophistication or nuance, but instead a determination to keep their focus uncluttered and clear in order to create rich musical palettes, as they have so successfully done with their debut release, Watching Mars."

“Make no mistake that [The Woodsheep] are the real deal. Their voices blend really well, and their songs are equally good: a rarity a la Everly Brothers. They restored my faith in music and hipster beards.” 

–The Outhouse Blog

"[The Woodsheep] are the Simon and Garfunkel of Kentucky." 
-Rosendale Cafe Guide,
Rosendale, NY

"One thing that is abundantly clear about The Woodsheep is how much they care about the quality of their performance."
-Tara Rueckert, Morehead State University 

Contact & Booking
Phone: 606-548-3654 (Andrew Preston)
Email: thewoodsheepband@gmail.com

Other Information
Upcoming and Past Tour Dates

Weddings, Private Events, & Live Sound

Lessons, Workshops, & School Events


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 in their ever-evolving eastern Kentucky home by shoring up their own roots. Andrew Preston (featured songwriter by the International Bluegrass Music Association in 2015) formed The Woodsheep in late 2015, and in only a year collected an impressive repertoire of original Americana music, Appalachian folk standards, and a year-long North American tour to promote their debut record, Watching Mars, earning them international success and a reputation for quirky showmanship and fine-crafted musical skill. As of 2018, they've released their sophomore record, Sleeping Under Stars, followed by another U.S. tour to promote the new music. For most performances, the band is comprised of Melissa Caskey and Matt Holleran, and have included other musicians in their performances. They have have worked with acts including The Price Sisters, Jocelyn Mackenzie of Pearl and the Beard, and The McLain Family Band. They have toured across the United States, Ireland, the U.K., and The People's Republic of China. Learn More.

Featured Music Videos

Live Simply


Wildcat - LIVE

Perspective of a Winter Leaf

The Peach Tree - LIVE

Sun On My Side - LIVE


The Woodsheep are proudly sponsored by Ale81