The Darkest Night of the Year

The Darkest Night of the Year is a Christmas album by the group Over the Rhine, released independently in 1996. It is their fifth studio album overall, and the last to feature the band's original lineup.

The album features six interpretations of traditional Christmas songs, three original instrumentals, three vocal compositions, and a second version of "Silent Night" featuring Terri Templeton, who was touring with Over The Rhine as a secondary vocalist at the time. Ten years later, Over The Rhine would release a second Christmas album, Snow Angels with a greater emphasis on original compositions.

This album is notable for being the first Over The Rhine album not to feature the photography of Michael Wilson. The cover illustration is by David Sheldon. Additionally, this is the only full-length OTR album to feature bassist Chris Dahlgren, who began touring with the band in 1996 to accommodate Linford Detweiler's move to keyboards.