Heywood co-founded the New England Labor Reform League in 1869 with individualist anarchist William Batchelder Greene.

The league advocated for the "abolition of class laws and false customs, whereby legitimate enterprise is defrauded by speculative monopoly."

[4] In May, 1872 Heywood, a supporter of women's suffrage and free love activist Victoria Woodhull's free speech rights, began editing individualist anarchist magazine The Word from his home in Princeton, Massachusetts.

[5] He was tried in 1878 for mailing "obscene material", his pamphlet Cupid's Yokes: or, The Binding Forces of Conjugal Life: An Essay to Consider Some Moral and Physiological Phases of Love and Marriage, Wherein is Asserted the Natural Right and Necessity of Sexual Self-Government, which attacked traditional notions of marriage – at the instigation of postal inspector Anthony Comstock, who also had Truth Seeker editor D. M. Bennett arrested.

Convicted of violating the 1873 Comstock Act, Heywood was sentenced to two years' hard labor[6] at the Norfolk County Jail.