In 1953, Rich married Alfred Haskell Conrad, an economics professor at Harvard University she met as an undergraduate. She said of the match: "I married in part because I knew no better way to disconnect from my first family. I wanted what I saw as a full woman's life, whatever was possible." They settled in Cambridge, Massachusetts and had three sons. In 1955, she published her second volume, The Diamond Cutters, a collection she said she wished had not been published. That year she also received the Ridgely Torrence Memorial Award from the Poetry Society of America. Her three children were born in 1955 (David), 1957 (Pablo) and 1959 (Jacob).
We are, I am, you are by cowardice or courage the one who find our way back to this scene carrying a knife, a camera a book of myths in which our names do not appear.“ ” From "Diving into the Wreck" Diving into the Wreck: Poems 1971–1972 (1973)
The 1960s began a period of change in Rich's life: she received the National Institute of Arts and Letters award (1960), her second Guggenheim Fellowship to work at the Netherlands Economic Institute (1961), and the Bollingen Foundation grant for the translation of Dutch poetry (1962). In 1963, Rich published her third collection, Snapshots of a Daughter-in-Law, which was a much more personal work examining her female identity, reflecting the increasing tensions she experienced as a wife and mother in the 1950s, marking a substantial change in Rich's style and subject matter. In her 1982 essay "Split at the Root: An Essay on Jewish Identity", Rich states: "The experience of motherhood was eventually to radicalize me." The book met with harsh reviews. She comments, "I was seen as 'bitter' and 'personal'; and to be personal was to be disqualified, and that was very shaking because I'd really gone out on a limb ... I realised I'd gotten slapped over the wrist, and I didn't attempt that kind of thing again for a long time."
Moving her family to New York in 1966, Rich became involved with the New Left and became heavily involved in anti-war, civil rights, and feminist activism. Her husband took a teaching position at City College of New York. In 1968, she signed the “Writers and Editors War Tax Protest” pledge, vowing to refuse tax payments in protest against the Vietnam-America War. Her collections from this period include Necessities of Life (1966), Leaflets (1969), and The Will to Change (1971), which reflect increasingly radical political content and interest in poetic form.
From 1967 to 1969, Rich lectured at Swarthmore College and taught at Columbia University School of the Arts as an adjunct professor in the Writing Division. Additionally, in 1968, she began teaching in the SEEK program in City College of New York, a position she continued until 1975. During this time, Rich also received the Eunice Tietjens Memorial Prize from Poetry Magazine. Increasingly militant, Rich hosted anti-war and Black Panther fundraising parties at their apartment; tensions began to split the marriage, Conrad fearing that his wife had lost her mind. The couple separated in mid-1970 and shortly afterward, in October, Conrad drove into the woods and shot himself.
In 1971, she was the recipient of the Shelley Memorial Award from the Poetry Society of America and spent the next year and a half teaching at Brandeis University as the Hurst Visiting Professor of Creative Writing. Diving into the Wreck, a collection of exploratory and often angry poems, split the 1974 National Book Award for Poetry with Allen Ginsberg, The Fall of America. Declining to accept it individually, Rich was joined by the two other feminist poets nominated, Alice Walker and Audre Lorde, to accept it on behalf of all women "whose voices have gone and still go unheard in a patriarchal world." The following year, Rich took up the position of the Lucy Martin Donnelly Fellow at Bryn Mawr College.