"It was nice to have taken so much time away and to apply what I had learned from leading these songwriting retreats, in terms of all the little jump starts you give yourself when you have a little collapse – when you’re at a fork in the road with your writing or with your confidence.

This is Williams' first studio album in six years, after a time spent writing books and giving songwriting retreats.

[3] Songwriting for the album began while touring and being inspired by reading about smalltown America;[4][5] it explores themes of accepting life as it is, detaching from judgement,[6] and being optimistic[7] and is based on Williams' songwriting and personal history.

[8] Debra Kate Schafer of The Aquarian Weekly characterized this work as "there is no surprising moment on the record, which is beneficial in the sense that you’re not slapped in the face with something too edgy or radical, but it also means that there is no standout moment either" and continued that many individual songs are standout, but the album is not cohesive.

[1] Lyndon Bolton of No Depression called this "a compelling insight into how Dar Williams has accepted change and lives with contentment" and "her unique blend of encouragement and resilience is as much a gift to the listener as it must be for those who have been on her retreats"[9] In a feature for Portland Press Herald, Aimsel Ponti wrote that this album displays Williams' "exemplary songwriting" and emphasized the emotional impact of “Little Town”.