In 1996, following his graduation, Goldberg moved back to New York and once again concentrated on music. Among others, he performed with Mark Turner, Gregory Tardy, and Betty Carter, whom Goldberg first met as a founding member of her Jazz Ahead program while at Harvard. In 1998, he formed the Aaron Goldberg Trio with Reuben Rogers on bass and Eric Harland on drums, and the trio released their debut album, "Turning Point", on J Curve in 1999. He also began what would become a lengthy association with saxophonist Joshua Redman, and toured extensively with him. In 2001, as he continued to tour with Redman, the Aaron Goldberg Trio released a second album, "Unfolding", on J Curve. Goldberg was on the road with Redman full-time until 2002, when he returned to New York to perform with jazz performers including Nicholas Payton, Al Foster, Freddie Hubbard, and Stefon Harris. In addition, inspired by a passion for the country's music, he traveled frequently to Brazil between 2000 and 2002. In 2005, he toured South America with Madeleine Peyroux, joined the bands of Kurt Rosenwinkel and Wynton Marsalis, and performed worldwide as a member of the Lincoln Center Jazz Orchestra.