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Last Updated on June 1, 2019, by eNotes Editorial. Word Count: 1319

Act 1
The Night Thoreau Spent in Jail takes place in Concord, Massachusetts, and the surrounding area. As the stage directions note, "time and space are awash here." The play starts in one time period and then abruptly shifts around to many other times and places. At all times throughout the play, Henry David Thoreau's jail cell can be seen in the background. The play starts at its latest point in time, during a Concord winter when Ralph Waldo Emerson is an old man, walking with his wife, Lydian. With his wife's help, Waldo remembers the name of Henry (Thoreau), who was his best friend. With this realization, the action shifts to Henry's jail cell, when the writer is a young man.

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Henry's mother asks Henry why he is in jail, and he gives vague answers, a tactic that he uses throughout the play. Henry shows what his mother calls his strangeness by questioning the order of the alphabet. Henry's brother, John, comes into the jail cell, and their mother leaves. The location shifts to a sunny field at an earlier time, when Henry has just returned from Harvard. Henry and John talk about Henry's education, which Henry counts as worthless except for hearing the lectures of Waldo, whom he says he wants to emulate. Back in the jail cell, Henry talks with his cellmate, Bailey, who has been accused of burning down a barn; Bailey has been waiting for his trial for three months, a fact that outrages Henry.

Henry tries to talk to Bailey about conformity, but Bailey is not an educated man. Henry teaches Bailey how to spell his name, then grabs a chair from the jail cell and moves to the front of the stage, shifting back in time to when he was a teacher. He is interrupted by Deacon Nehemiah Ball, the Chairman of the Concord School Committee, who criticizes Henry's deviations from the approved school textbooks. Henry gets into a theological argument with Ball, who is outraged at Henry's transcendentalist beliefs, and Henry provokes the class to laugh at Ball. John later tells Henry he should apologize to save his job, which Henry does. However, although Ball excuses him, he forces Henry to whip six of his students for laughing. Henry reluctantly does this, then quits teaching, just as Waldo quits his position as Unitarian pastor, in another time-space shift.

Henry proposes to John that they start their own unconventional school, which they do. Henry and John stand in a meadow teaching a number of students, including Ellen, a beautiful young woman who is much older than the class. Henry criticizes Ellen for trying to take notes, a method used in conventional schooling. The action shifts back to the jail cell, where Bailey has successfully learned how to write his own name. Henry encourages Bailey to unlearn it and remain uneducated. Henry pushes the jail cell's locker box to the front of the stage, where it becomes a boat by a pond. John tells Henry their school is losing all of its students. John leaves, and Ellen enters. Henry uses the opportunity to invite her for a boat ride, during which he tries to explain his transcendentalist views to her and profess his love to her; both attempts are unsuccessful, and Henry suggests that Ellen go to church with John.

Back in the jail cell again, Henry proclaims to the sleeping Bailey that they are freer in prison than the outside community, who must conform. At the front of the stage, a crowd of churchgoers files out of the church, Ellen on the arm of John. Although Lydian attempts to mask Waldo's satirical comments, it is clear from Waldo's conversation with Deacon Ball that Waldo is critical of organized religion. This belief is underscored by the appearance of Henry, who, to the dismay of his mother and Ball, is working on Sunday. Later, Henry and John talk about Ellen's refusal to marry John. John dies from blood poisoning, cutting himself with a dirty razor.

The action shifts back to the day when Henry hires on as Waldo's handyman and tutor for Edmund, Waldo's son. This is the beginning of the friendship between the two men. Waldo insists on paying Henry, but Henry will not take money and instead asks for the future use of a portion of Waldo's wooded estate, Walden, for an experiment. Waldo also asks for Henry's occasional help in polishing his speeches. Back in the jail cell, Henry and Bailey talk about Walden, where he remains secluded from civilization, except when he has to go into town for supplies. The action shifts, and Henry walks into town to get his shoe fixed. Constable Sam Staples comes up to Henry and serves him with a bill for unpaid taxes. Henry refuses to pay, since he does not support the way the tax money is being spent. Sam reluctantly takes Henry to jail. Waldo gets a note saying that Henry is in jail and goes to see him. Sam pleads with Henry to pay his tax, but Henry, cryptic no longer, finally explains that he is not paying his tax because it is going to pay for the war against Mexico which he does not support. The act ends with Waldo asking Henry what he is doing in jail, while Henry asks what Waldo is doing out of jail, implying that Waldo should be protesting in jail with Henry.

Act 2
Lydian sends Edward with Henry to go huckleberry hunting. Edward says he wishes Henry was his father, a sentiment he later repeats to his mother. Lydian suggests that Henry should get married, and he says nature is his chosen bride. Back in the jail cell, Bailey asks Henry to be his lawyer, but Henry refuses. The action shifts to Walden Woods, where Henry feeds an escaped slave, Henry Williams, on his way to Canada. The time shifts ahead, and Henry and Waldo argue about the fact that Waldo is not protesting the release of slaves like Williams, who has been shot. Henry accuses Waldo of not practicing what he preaches and encourages Waldo, who has much more influence than Henry, to speak out against slavery and the war. Waldo hesitantly agrees, and Henry rushes off, ringing the town bell and announcing that Waldo is going to make a speech. Lydian comes up and tells Henry that Waldo is not coming, that he has chosen to think over the matter and write a carefully worded essay describing his position. The crowd disperses. Henry tries to get their attention again, but this time, the bell makes no sound.

Back in his jail cell, Henry is in the grips of a nightmare. The Mexican war rages around his sleeping body, and all of the major characters in the play are in the battle. Edward Emerson is a drummer boy, Sam Staples is a sergeant, Bailey is a soldier, Ball is the general, and Waldo is the president. Henry tries to talk to Waldo, but no sound comes out. When Ball asks Waldo for instructions, he says that he needs to collect his thoughts. Williams appears as a Mexican soldier. Edward is wounded, but Waldo ignores this fact, saying he needs more time to think and write a carefully worded essay. The unseen voice of then-Congressman Abraham Lincoln advocates stopping the war. John comes on the scene in a soldier's uniform and gets killed.

Back in the jail cell, Henry wakes up from his nightmare and finds Sam is there with breakfast. He also tells Henry that somebody paid his tax for him and that he is free to go. Henry is outraged and forces Sam to tell him that it was his Aunt Louisa who did it. Henry leaves the cell, telling Bailey that he is leaving Walden because he has to stop hiding in the woods and take a more active stand against society's injustices.

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