Hammond was born on May 15, 1950 in Washington, D.C., the son of Colonel Thomas West Hammond, Jr. by his wife Eileen Hammond (née Bennett). While Hammond's father was a U.S. citizen and an officer in the U.S. Army, his mother was English and had played a role in Much Too Shy in 1942. Hammond has one elder brother, David (b. 1946). Hammond's parents had met and married in London during World War II when his father had been posted there. After the war, the couple moved to the U.S. permanently, and because the Colonel had an army job, the family moved numerous times to various army stations across the country during Hammond's childhood. Col. Hammond died in 1970.
Hammond was 11 years old when he made his acting debut in the Broadway play The Complaisant Lover in 1961. At the same time, he began to shoot for the 1963 film Lord of the Flies, which marked his film debut. After this, Hammond played what was to be his most notable screen role: Friedrich von Trapp (the elder of the two boys) in the 1965 hit The Sound of Music.
Hammond's next acting role came in 1970, when he appeared in Conduct Unbecoming, his first role as an adult. In 1972 Hammond appeared as Peter Linder in Skyjacked. In 1973 he made a guest appearance on The Brady Bunch in season 4, episode #090, "The Subject Was Noses", as the high school hunk, Doug Simpson, who loses interest in Marcia after her tragic football accident. That year Hammond also appeared in The Waltons episode "The Townie", as Theodore Claypool Jr.

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