The album produced two singles on the US Billboard Hot Country Songs chart with the title track and "Draw Me a Map".

[1] It features many collaborations, including The Del McCoury Band, Alison Krauss, Chris Thile, and Miranda Lambert.

Via his website, Bentley explained the reason behind Up on the Ridge, saying: “This album won’t come as a surprise to my hard core fans, they've asked me: ‘when are you going to make a bluegrass record?’ And I was just waiting for the right time.

I wanted each song to have something special about it, and in the end I think each song really does have its own thing going on.”[2] In an interview with Billboard Magazine, Capitol Records Nashville president and CEO Mike Dungan commented on Up on the Ridge saying that "The album was supposed to be a side project, but it's grown into something much more....He had a real sense of direction and made a vehicle for people to hopefully discover this music".

She praised the sound of the album, saying that it "is built on a bedrock of bluegrass sensibility, but is colored by Dierks' various country, rock and folk influences.