On May 15, 2008, it was reported that the Bosstones would be embarking on a short United States tour in July with the Dropkick Murphys. During the tour, the Bosstones made three stops at Boston Red Sox minor league ballparks. On October 20, 2008, their website announced that they would return to the Middle East in Cambridge to play an eleventh Hometown Throwdown on December 26–29. In late 2008, the game "Rock Band 2" was released and featured a re-recorded version of "Where'd You Go?" that the band had recorded earlier in the year. On 4 November 2008, a MySpace blog announced the recording of a new album, and streamed two new songs, "The Impossible Dream" and "Next to Nothing". On July 29, 2009, the band announced the completion of tracking for the album. On October 16, 2009, the album title was announced to be "Pin Points and Gin Joints" and a free download of the song "Graffiti Worth Reading" was made available. The release date was later stated as December 8, 2009.