Bernstein began playing piano when he was eight but switched to guitar when he was thirteen, learning the instrument primarily by ear. He studied jazz at Rutgers University with Ted Dunbar, and Kenny Barron.
He began his caeer playing the JVC Jazz Festival in 1990, he then appeared on albums with Jesse Davis, Lou Donaldson, Larry Goldings, Michael Hashim, Geoff Keezer, and Melvin Rhyne. He released his first album as a leader with pianist Brad Mehldau. He has also worked with Jimmy Cobb, Tom Harrell, Nicholas Payton, Diana Krall, Lee Konitz, Eric Alexander, Joshua Redman, Dr. Lonnie Smith, and Walt Weiskopf. He is a member of the Blue Note 7.