Caldwell graduated from Hendrix College in 1944 and attended the University of Arkansas as well as the New England Conservatory of Music.

At the New York City Opera, Caldwell staged Der junge Lord and Ariadne auf Naxos (with Carol Neblett), both in 1973.

She became the second woman to conduct the New York Philharmonic in 1974 with an all-female programme of composers including Ruth Crawford Seeger, Lili Boulanger and Thea Musgrave.

[3][1][4] In 1976, she both conducted and directed Il barbiere di Siviglia (with Sills and Alan Titus), which was televised over PBS.

Bicentennial opera Be Glad Then, America with Odetta (Muse for America), Donald Gramm (various patriots), Richard Lewis (King George III), David Lloyd (Town Crier), and the Penn State University Choirs and the Pittsburgh Symphony.

Caldwell also directed one non-musical production, the 1981 Lincoln Center staging of Shakespeare's Macbeth, presented on cable TV in 1982.

It starred Philip Anglim and Maureen Anderman, with a then-unknown Kelsey Grammer in the supporting role of Ross.