Bailey
Bailey is Henry's vagrant cellmate, who has landed in prison after he fell asleep in somebody's barn and burned it down by accident. Henry tries many times to talk to Bailey about his crusade against conformity, but Bailey is an uneducated man, who says he cannot even write his own name, much less understand Henry's preaching. Henry shows Bailey how to write his name but then encourages him to unlearn it, since writing will only get him in trouble. Bailey is excited to hear about Henry's place in Walden Woods and says that he [Henry] had a place to call home. Bailey gets panicked about the idea of a trial and asks Henry to be his lawyer, since he is an educated man. Henry refuses, and Bailey frantically asks him what he can do. Although he does not believe in it, Henry suggests prayer, and Bailey asks Henry to help him pray. Henry is outraged when he finds out that Bailey has been waiting three months for a trial, and at the end of the play, he threatens to sit in the jail cell until Sam Staples intervenes on the behalf of Bailey. Bailey is touched, since nobody has ever stuck up for him before, and says that when he gets out of jail, he may come visit Henry at Walden Woods. However, Henry says that the Walden stage of his life is over, and he needs to rejoin civilization and take a stand. In Henry's nightmare, Bailey is a civilian soldier who refuses to fight.

Deacon Nehemiah Ball
Deacon Nehemiah Ball, a religious leader who also acts as the chairman of the school board, does not like Henry. When Ball visits Henry's class, he is shocked that Henry is deviating from the authorized textbooks and considers Henry's transcendental view of God to be blasphemous. Ball is also outraged when he finds Henry working on Sunday. When Henry refuses to pay his taxes, Ball is the first to suggest throwing him in jail. In Henry's nightmare, Ball is the General who advocates destroying the enemy and who incites the Federal forces to kill.

Edward Emerson
Edward Emerson is the son of Waldo and Lydian, and he wishes Henry was his father instead of the often absent Waldo. Edward's parents hire Henry to work as a handyman and serve as a companion and tutor to Edward. Henry takes Edward hunting for huckleberries, and Edward gets excited and drops his basket of berries. Although he is upset, Henry consoles him, saying that he is helping to fertilize the earth to make more huckleberries. Edward is delighted when Henry puts gloves on the claws of Lydian's chickens—so that they cannot trample Lydian's flowers anymore. In Henry's nightmare, Edward plays a drummer boy who is wounded in the fight. When Henry carries the wounded boy to Waldo, the president in the dream, the dream Waldo echoes his noncommittal statement from before, saying that he needs to write a carefully worded essay about the situation.

Lydian Emerson
Lydian is the wife and supporter of Waldo and encourages Henry to settle down, get married, and conform. Although Lydian appears to agree with many of Henry's ideas, she refuses to go against her husband by supporting Henry. Lydian is a lonely wife, since Waldo is often away giving lectures. She tells Henry that Waldo cannot possibly live up to the ideal image that Henry has painted of her husband. It is Lydian who comes in place of Waldo to tell Henry and the assembled crowd that her husband is not ready to speak yet. In Waldo's old age, Lydian helps her befuddled husband remember Henry's name, the event that starts the play.

Ralph Waldo Emerson
Ralph Waldo Emerson, one of America's greatest writers, is in this play shown to be an ineffective preacher when compared with Henry's activism. Waldo gives many lectures at Harvard outlining the beliefs of Transcendentalism, and he finds a willing acolyte in one of his audience members, Henry David Thoreau. Waldo hires Henry as a handyman and tutor for his son, Edward, in exchange for the use of a piece of Waldo's wooded estate. This arrangement later provides the location for Henry's Walden Woods project. Waldo spends much of his time writing or delivering lectures, much to the chagrin of his lonely wife, Lydian, who nevertheless supports Waldo completely. Waldo and Henry become great friends, but the friendship sours when Henry gets fed up with Waldo's lack of public protest.

Henry accuses Waldo of failing to use the whole of his massive influence to speak out against such injustices as slavery and the war in Mexico. Waldo marvels at the fact that Henry is a living, breathing example of the principles that he lectures on but is unable to adopt an activist lifestyle of protest himself. Instead, he prefers to work within the laws and write his lectures and essays. When Henry challenges Waldo to become a greater activist by speaking to the town, Waldo tentatively agrees but backs out after Henry has already gathered a crowd. Waldo sends Lydian to let Henry know that Waldo will not be giving the speech. At the end of the first act, Waldo asks Henry what he is doing in jail, while Henry counters, asking Waldo why he is out of jail. In other words, if Waldo really practiced what he preached, he would refuse to pay his taxes and protest in jail as Henry is. In Henry's nightmare, Waldo is the president who refuses to acknowledge the war tragedies that are happening around him or make any decisions; instead, he says he needs to write careful essays about them, echoing his earlier message about why he cannot speak out like Henry.

Farmer
The Farmer appears twice when Henry's actions draw a crowd, and he claims that Henry is always starting false fires, as when he says Waldo is going to give a speech and Waldo does not. In Henry's nightmare, the farmer serves as a soldier.

Henry
See Henry David Thoreau

Henry's Mother
Henry's mother does not understand why Henry always acts so strange and wishes he would just conform like everybody else. Henry's mother calls Henry by his official name, "David Henry," even though Henry prefers to go by his middle name. She disdains Henry's working on Sunday and prays that Ellen Sewell will accept John's marriage proposal. At John's funeral, she tries to get Henry to pray, but Henry is unable to pray to a God that felt it necessary to take John.

Ellen Sewell
Ellen Sewell is a young woman who attracts both Henry and John and who declines John's marriage proposal. Ellen is much older than the other students in Henry's and John's school, although she asks to be able to study with them. She is intrigued, then turned off, by Henry's transcendental beliefs, and Henry suggests that she go to church with John. Although she does accompany John to church, she claims that her father is forbidding her from marrying either Henry or John. However, Henry and John both believe that she wants to have both brothers. When John dies, Ellen is out of town, so she asks Henry what has happened. Henry is very rude to her, describing John's death in very graphic terms, which shocks her at first. In the end, however, she suggests that maybe they are meant to transcend John's death, an admission that makes Henry believe Ellen is starting to understand his beliefs.

Constable Sam Staples
Sam Staples is the law enforcement officer in Concord who reluctantly throws Henry in jail. Sam is a good-natured man, who first of all serves Henry with his bill for unpaid taxes, then offers to loan Henry the money to pay for them. Henry is outraged at this suggestion and forces Sam to take him to jail. Sam does not understand why Henry will not just pay his taxes. At the end of the first act, Henry explains that he does not want his tax money to support the Mexican-American war. This is the first time that Henry has stated outright why he is in jail, a question that it posed at the beginning of the first act but not answered until this point. In Henry's nightmare, Sam is a Sergeant who inspires his troops to hate and who forces Henry and Bailey to take guns they do not want.

Henry David Thoreau
Henry David Thoreau, considered one of America's greatest writers, is the fiery protagonist who goes to jail. In the beginning of the play, Henry is in jail, but the audience does not find out until the end of the first act that it is because he does not want to pay the taxes that will support the Mexican-American war. Henry is an uncompromising believer in casting off the chains of conformity and deliberately suggests that society should do things differently, such as starting the alphabet with a different letter. Because of these ideas, his mother, and indeed many of the townspeople, find Henry strange. Henry is a Harvard-educated man but does not believe in conventional education. He tries teaching his open-minded beliefs in the strictly censored school, and when that fails, he opens his own ill-fated school with his brother, John. He is initially attracted to Ellen Sewell but realizes that his brother, John, would make a better match, although Ellen turns John down. After John's death, Henry's views on organized religion and his belief in a caring God deteriorate even more.

A devoted disciple and friend of Ralph Waldo Emerson, Henry spends all of his energies trying to adhere to the ideals that Waldo lectures about. At one point, Henry hires on as Waldo's handyman and the tutor of Waldo's son, Edward, in exchange for the use of part of Waldo's wooded estate, which later becomes Thoreau's Walden. Henry encounters an escaped slave, Williams, at Walden and treats him as a free man. Henry is distraught when he hears that Williams was shot as he was trying to make his way to Canada and uses the incident to launch an argument about Waldo's lack of activism. Henry accuses Waldo of not practicing what he preaches, even though Waldo has much more influence than Henry and could do more good. Waldo tentatively agrees to give an impromptu speech against slavery and the war in Mexico but backs out, leaving Henry to try, unsuccessfully, to get the attention of the frustrated townspeople. In Henry's nightmare, he is initially sleeping as the war rages around him. Sam Staples wakes Henry up within his dream, forces a gun in his hand, and forces him to join the nightmarish war. When Waldo appears as the president, Henry tries to talk to him, but Waldo cannot hear anything that he is saying and refuses to comment on the war or make any decisions. At the end of the play, Henry wakes up to find that his tax has been paid by his Aunt Louisa, a fact that angers him. When Henry leaves the jail, he vows to leave Walden and take his activism to the next level.

John Thoreau
John Thoreau is Henry's much-loved brother, who shares many of Henry's beliefs but does not have the same conviction as Henry. John welcomes Henry home from Harvard, and the two brothers discuss their lack of faith in conventional education. However, John convinces Henry to apologize to Deacon Ball so that Henry can save his job. After the school founded by Henry and John fails, John goes back to his job at the pencil factory. Both John and Henry are attracted to Ellen Sewell, a young woman who asks to join their school. When Henry's attempt to win her love fails, he encourages her to see John. However, although she accompanies John to church, Ellen does not accept his marriage proposal because her father does not like the Thoreau brothers. Also, as John and Henry discuss, it appears that she wants both brothers, not just one or the other. John dies from blood poisoning after he cuts himself shaving with an old razor. In Henry's nightmare, John is a Federal soldier who dies at the end of the dream.

Waldo
See Ralph Waldo Emerson

Henry Williams
Henry Williams, an escaped slave who derives his first name from Thoreau and his last name from his former owner, encounters Henry in Walden Woods. Although Williams is suspicious of Henry at first, he is soon amazed that Henry treats him as an equal. Henry gives Williams food and is distraught when he hears that Williams has been shot while trying to escape to Canada.