Anastasio began playing the drums at a young age and turned to guitar while a teenager. He went to Princeton Day School for junior high, where he began to write music for the first time. For high school, he went to Taft School, where he founded his first two bands, Red Tide and Space Antelope, respectively. After high school, he went to the University of Vermont from fall of 1983 to spring of 1986 (except for spring of 1984). It was here that he met teacher and composer Ernie Stires, who taught him techniques for composition and arrangement. It was here that he also hosted a morning radio show, called Ambient Alarm Clock. After the UVM, he attended Goddard College from fall of 1986 to spring of 1988. It was here that he wrote The Man Who Stepped Into Yesterday.
His mother, Diane, was an editor of Sesame Street Magazine. He wrote stories, songs, and albums with her. His father, Ernie, was the Executive Vice President of Educational Testing Services. This company is most noted for administering the SAT and other aptitude tests.
He plays a custom-made hollow-body electric guitar, built by Paul Languedoc. His set-up includes a wah wah pedal, a phase shifter, a volume pedal, celestain speakers, and two TS-9 Ibanez Tube Screamers. Two of his guitars have images of his dog, Marley, inlaid on the headstocks.
Trey's other projects include the Trey Anastasio Band, a swing/jazz ensemble with a five-piece horn section that is highly influenced by the work of Duke Ellington; Surrender To The Air, a free jazz project with mandolin-player Jamie Masefield and Kozmic Krew member Michael Ray; and Oysterhead, a rock trio with former Police drummer Stewart Copeland and Primus bassist and bandmaster Les Claypool.