Following surgery in the 2006–07 offseason, Pickering signed with the Kansas City T-Bones of the independent Northern League and played the 2007 season there. He batted .310 with 18 home runs and 83 RBI in 89 games.
In 2008, Pickering signed with the Bridgeport Bluefish of the independent Atlantic League, but was released on July 13 after batting only .265. He then signed with the Schaumburg Flyers of the Northern League and hit .298 with 14 home runs in only 37 games.