Gaskin was born in Denver, Colorado and served in the United States Marines from 1952 to 1955. In the 1960s, he moved to San Francisco and taught English, creative writing, and general semantics at San Francisco State College, where he was a student of S. I. Hayakawa. His writing class became an open discussion known as Monday Night Class, which involved up to 1500 students.

In 1970, Gaskin was part of a caravan of 60 vehicles that crossed the United States to settle 60 miles south-west of Nashville, Tennessee, forming a community called "The Farm", which the Wall Street Journal came to call "the General Motors of American Communes". This community was "a platform from which to launch efforts to improve the lot of poor and indigenous peoples, whales, and old growth trees" For example, raising 1,200 earthquake-resistant homes in Guatemala as well as several public buildings and water lines to 5 villages, sending independent dosimetry teams after the Three Mile Island accident and the Chernobyl disaster, or giving the Rainbow Warrior equipment to scape a Spanish harbor.

He went to prison in 1974 for marijuana possession, as he had planted several marijuana plants with other members of The Farm. He served one year of a three-year sentence. While in prison, a class action suit on his behalf returned voting rights to more than a quarter of a million convicts.

In Volume One: Sunday Morning Services on the Farm and earlier talks, Stephen Gaskin produced a substantial body of spiritual teaching. His ideas are now contained in books and tapes of the Services which were published by the Farm. They speak of magic, energy and life in community as well as of service to humanity.

Gaskin was recipient of the first Right Livelihood Award (Alternative Nobel Prize) in 1980 and an inductee into the Counterculture Hall of Fame in 2004. He was awarded the Golden Bolt Award by The Farm Motor Pool (for helping buy a lemon semi), and won the Guru-Off (without even entering), racking up 77 points to Krishnamurti’s 73.

Gaskin works as an international activist and speaker, and he continues to write. His topics range from advice on all aspects of communal life and farming to CB radio, the counter-culture, spirituality, drug law reform, and social and spiritual issues. He was a drummer in The Farm Band, an early Jam Band which toured in the seventies and eighties. His most recent books are revised and annotated versions of Monday Night Class and The Caravan.