Sherwood is a lawyer with a private practice in Pittsfield, MA. He was born in a small town in upstate NY, attended public schools and went on to Dartmouth College, graduating in 1968. After teaching school in northern New Hampshire for a year after college, he married his wife Carol and together they joined the Peace Corps, serving in La Laguna, Panama from 1969-1971.
After Peace Corps, Sherwood went to the Antioch School of Law graduating in 1975. Following a brief sojourn in Pennsylvania, he and Carol moved to the Berkshire Hills of western Massachusetts.
Sherwood opened his own practice in the early 1980’s. He is active in Democratic politics and served four terms as a State Representative in the Massachusetts legislature from 1983 to 1990.
From 1995-1997, he also took a sabbatical from his law practice and served for two years on the senior staff of the Peace Corps in Washington, directing “Domestic Programs” for Peace Corps, working with returned volunteers around the country.
He continues to practice law today in Pittsfield, MA