Thoreau actually discusses the time he got arrested for refusing to pay his poll tax in his essay, "On the Duty of Civil Disobedience." He says that he has not paid his tax for six years and that he was "put into a jail once on this account." He marvels that he is treated thus, as though he "were mere flesh and blood and bones" rather than putting his mind or even body to some kind of use. Thoreau apparently found his one night in jail quite interesting, and he spent his time talking to the other inmates, especially his roommate (who was content because he was sheltered and fed there). He says that going to jail was "like travelling into a far country"; in other words, it felt like going somewhere totally new and different that he never expected to see. He describes his activities and thoughts and feels that he gets to know Concord even better as a result of this experience.

It is in chapter 8 that Thoreau discusses his arrest for failing to pay taxes. Although Thoreau's arrest was caused by his failure to pay taxes, what is most significant is his reasons why. His reasoning was based in his protest of slavery. Thoreau believed that the U.S. war with Mexico in 1846 was rooted in an attempt to extend slvery west. He believed the Mass. poll tax was immoral since it would further the war effort, and as a result he had no alternative but to deny his money go to such a cause. Thoreau was part of the Transcendentalist movement in the U.S. which believed that one should side with morality, something that man made laws sometimes ignored. Thoreau's experience would result in his essay 'Civil Disobedience' which has left its mark on India's independence from Britain, as well as the American Civil Rights movement.