The album is the first since the departure of cellist Gretta Cohn[1] whose instrumentation was a fixture of the band's 2003 release The Ugly Organ.

The album features significant five-piece horn arrangements courtesy of Nate Walcott.

Each track in the album tells a different story of faults that the inhabitants of Happy Hollow portray that seem at odds with the town's "perfect" image.

[5][6] "Dorothy at Forty" was released as a single on July 11, 2006; it included the non-album tracks "The Bitter End" and "The Censor".

[9] On August 21, 2006, Happy Hollow was made available for streaming through their Myspace, prior to its release the following day through Saddle Creek Records.

[19] In April 2008, the band went on a tour with Capgun Coup; the trek included performances at Not Brooklyn Fest and Mission Creek Music and Arts Festival.