Awarding the album four stars at AllMusic, Mark Deming writes, "Didn't He Ramble shows that as a performer and a songwriter, Hansard can create powerful and satisfying work that's up to the standard he set with the Frames, and this is a step up from 2012's impressive but uneven Rhythm and Repose.

"[9] Rating the album four stars for The Daily Telegraph, Marcus Chilton says, "On Didn't He Ramble, he brings his expressive voice and interesting lyric-writing to traditional-minded Irish ballads such as McCormack's Wall, while Her Mercy uses horns in a stirring soulful way.

"[7] Craig Manning, rating the album an eight and a half out of ten for AbsolutePunk, believes, "even in his least effective moments, though, it's impossible to ever doubt Hansard's honesty or conviction, and that level of trust he's earned with his listeners is what makes him one of the best songwriters living.

"[4] Giving the album a seven out of ten from Under the Radar, Matt Conner explains, "Ramble, perhaps more than any Hansard release, feels intimate and confessional, marked by encounters with grace and mercy and wrapped in lessons of loss and endurance.

"[12] Alexandra Fletcher, indicating in a seven out of ten review by PopMatters, responds, "He writes beautiful homages to love, and equally ornate eulogies to it, but this record feels less about heartache and more about introspection, patriotism, encouragement and healing—and it works.