Terry & the Pirates were led by guitarist/singer Terry Dolan, a Connecticut native who relocated to San Francisco during the area's notorious Summer of Love in 1965. Dolan played out locally during this time, performing at coffeehouses, clubs, and festivals alongside such renowned national acts as Elvin Bishop, B.B. King, Taj Mahal, and Blue Cheer, among others. (Dolan's merging of both folk and rock tended to confuse some at the time as Dolan refused to be pigeonholed solely to either of the styles.) He befriended another local outfit, Country Weather, from which he would often borrow members for his own recordings and performances throughout the years (while their guitarist, Greg Douglass, would eventually leave the group to permanently focus on working with Dolan). Country Weather backed Dolan for demos he laid down in the summer of 1970, which were aired on local radio stations KSAN and KMPX.