Counter-cultural leader best known for his presence in the Haight Ashbury in the 60s and for co-founding "The Farm", a hippie commune in Tennessee. Gaskin was an assistant professor at San Francisco State College in the mid-1960s. He left his academic position and began holding weekly Monday Night Classes. For more than five years, these weekly classes discussed politics, religion, acid, sex, and love and were eventually attended by more than 1,000 people. In October 1970, Gaskin set out with hundreds of hippies in a caravan of 50 school buses and 40 other vehicles on a speaking tour of the United States. They landed in Tennessee in October 1971 where he co-founded the Farm with his wife, Ina May. At its peak the community had more than 1,500 members.

In recent years, Gaskin has acted as the general manager and production director for The Birth Gazette, a quarterly magazine about midwifery. He has also founded a new non-profit named "Rocinante", a combination retirement community and midwifery center.