Witmer's 2005 album, Are You a Dreamer?, produced by Don Peris of The Innocence Mission and featuring Sufjan Stevens, received acclaim, including positive reviews from Pitchfork Media[2] and Entertainment Weekly.

[6] Witmer's lyrics are poetic and thoughtful; his guitar work, while simple-sounding, relies on complex fingerpicking.

The album was recorded as a project for an English class during Witmer's senior year of high school.

The album sold out, and indie label Burnt Toast Vinyl approached Witmer, asking to re-release it.

[7] Safe Away received a positive review from Allmusic: "Witmer proceeds through the setlist with the confidence and generosity of a seasoned songwriter, despite the journal-like candor of his lyrics.

"[1] Concerning the album's influences, he noted, "I was listening to a lot of ‘70s singer/songwriter stuff like Jackson Brown and Carol King and Neil Young and Van Morrison and I was going for a little bit of that style.

[10][14] Whereas Safe Away was guitar and vocals and Of Joy & Sorrow was more orchestrated, Witmer stated that Philadelphia Songs strikes a balance between his first two albums: “I just feel like I accomplished something that I’ve been trying to accomplish for a while.”[14] The album was produced by Blake Wescott and features instrumental work by The Six Parts Seven.

received a B+ review score from Entertainment Weekly: “His brand of happy anachronism is easy enough to fall into — if you can slow down long enough to enjoy it.”[3] In 2006, The Militia Group label re-issued his first album Safe Away as a special two-disc edition with new artwork and a bonus EP.

Happy Birthday Denison served as a fundraiser for Partners in Health and Musicians On Call, though no donations were required to download the songs.

Carry the Weight features James McAlister and Rosie Thomas on most songs, and Noah Harris.

It was influenced by landmarks in Witmer's life, including his marriage, his father's death, and his first child's birth.

[8][20] CJ Camerieri, Devin Greenwood, James McAlister, Charles Staub, and Rosie Thomas contributed to The Ones Who Wait.