In a July 2015 NPR interview, guitarist Josh Ritter stated that Weir was working on an album of "cowboy songs".

[5] On February 12, 2016, while performing at Sweetwater Music Hall for a benefit for Ring Mountain Day School, Weir debuted two new originals from the album; "Gonesville", and "Lay My Lily Down".

[8] Musicians on the album include Ritter, Josh Kaufman, Scott Devendorf, Joe Russo, and The Walkmen's Walter Martin, along with lyricists Gerrit Graham and Barlow.

"[13] Talking about "Lay My Lily Down", Mason prompted Weir on the content of the record, noting the song contained quite a bit of sadness.

NPR's Felix Contreras calls "Only A River" an emotional reflection on life that references the 19th-century American folk song "Shenandoah.

Rolling Stone's Elias Leight describes "Gonesville" as "Weir and his band shambling cheerfully here: The bass line hints at the verve of honky tonk, the harmonica scoots forward and the lead guitar spits lively licks.

A raft of backing vocalists join in during the chorus, adding to the cool, festive air, and "Gonesville" comes to a close with a jaunty group chant.

"[16] Weir stated that "Ki-Yi Bossie" was written "remembering some of the guys I'd met on the ranch who'd yearned for a simpler life and found themselves better outside of civilization.

"[20] Rolling Stone writer Richard Gehr wrote that "The highlight is his self-penned and unaccompanied "Ki-Yi Bossie", in which "a 12-step meeting under harsh fluorescent light" occasions a wry round of soul-searching, no wide-open spaces required.

[23] Andy Gill, writing for The Independent, wrote that "The widescreen south-western ambience is stippled with intriguing touches, like the shruti box and bowed guitar droning through "Gallop on the Run", and the rhythmic rattling chains of the death ballad "Lay My Lily Down"; though the most moving performance is Weir's plaintive solo piece "Ki-Yi Bossie", oozing empathy for a reluctant penitent alcoholic.

"[21] Not all reviews were positive; Boston Globe critic Matthew Gilbert wrote that "the manufactured atmosphere ultimately distances the listener.

With a few exceptions, including the song "Blue Mountain", the production also fails to find the best way to deploy Weir's voice, holding it too far back in the mix.