Witmer grew up in a Mennonite family in Lancaster, Pennsylvania, and began playing guitar as a high schooler. His guitar teacher was Don Peris, a local musician who, along with his wife, Karen, fronted the acclaimed folk-rock band the Innocence Mission. Peris would play a significant role in Witmer's creative development and would later produce several of his albums. Witmer's first project, recorded during his senior year of high school, was a 1995 cassette called My Luck, My Love. A few years later, he made his official debut with 1998's Safe Away, a sparse acoustic collection produced by Peris. The album introduced Witmer's earnest, intimate style, which evoked other young indie singer/songwriters of the era like Damien Jurado and Pedro the Lion's David Bazan. When its original pressing sold out, the album was picked up by Philadelphia indie Burnt Toast Vinyl, which also issued the follow-up.
Released in 2001, Of Joy Sorrow saw Witmer recalling an earlier generation of singer/songwriters with still organic but slightly heartier arrangements that recalled early-'70s releases by Cat Stevens or even Nick Drake. Released just a year later, his third album, Philadelphia Songs, took direct inspiration from Witmer's experiences moving to the city. By this point, he was touring regularly and had amassed a cache of solid reviews for his work. The 2003 covers album Recovered offered clean, uncluttered takes on classic songs by Fleetwood Mac, Carole King, and others, and was followed in 2004 by And Flows into the Sea, a release by his side project the River Bends.
Reuniting with the Perises, Witmer's 2005 solo album Are You a Dreamer? was given a wider release by West Coast label the Militia Group. It became something of a breakout release, receiving widespread critical acclaim. Capitalizing on its success, the label reissued Witmer's 1998 debut with bonus tracks in 2006 to help keep up momentum ahead of 2008's Carry the Weight. Recording the album in Seattle, Witmer pulled out all the stops to create a sonically rich, fully arranged studio album and enlisted guests like Rosie Thomas and James McAlister to play on the bulk of it.
Throughout his career, Witmer has tended to jump between different labels, and 2011's The Ones Who Wait first saw release via Tennessee imprint Mono vs. Stereo before getting picked up by Asthmatic Kitty a year later for a wider release. Founded by another sensitive but ambitious acoustic singer/songwriter, Sufjan Stevens, Asthmatic Kitty proved to be a good fit for Witmer's sensibilities, and they proceeded to release his self-titled eighth album in 2013. After that, his usually prolific output dropped off for several years as he moved with his family from Philadelphia back to Lancaster and started a carpentry business. Inspired by the home he and his wife bought and helped restore, 2020's American Foursquare was rich in domestic imagery and themes of family life. ~ Timothy Monger, Rovi