The main problem is the definition of freedom. Although actual physical slavery is an issue, so too are those who are "enslaved" to institutions, i.e., jobs and money. As the character Henry tells a runaway slave, ""Every man shackled to a ten-hour-a-day is a work-slave. Every man who has to worry about next month's rent is a money-slave."
This play was originally produced during the Vietnam era, and questions of authority, who grants freedom, and who has freedom were intensely debated.
Freedom, activism, and intellectualism are all themes that are explored in this play, but one large conflict revolves around freedom.
Thoreau is in jail for refusing to pay his taxes, and even though he claims his thoughts are free, he is physically inside a jail cell. This character didn't pay his local poll tax because he knew that the money would support two things he didn't believe in:
1.) slavery (which took away freedom)
2.) the Mexican-American war (some believed that the war was created only so that American could create more slave-holding southern states)
So in this case, the conflict was between Thoreau and his local town. Anyone who tried to, or offered to, pay Thoreau's tax for him, only angered Thoreau.
In addition, Thoreau's friend Williams (a run-away slave) is trying to escape to Canada in the pursuit of freedom. Thoreau helps Williams along the way, but unfortunately the ex-slave is stopped in Boston.
When Thoreau and Emerson (Waldo) discuss Williams, the two get into a heated argument about the difference between believing in freedom for all and between actually doing something about it. This conflict causes a major rift in their relationship.
Other plot points you might be able to connect with conflict:
- the students in the public school and their lack of freedom of thought and expression
- Ellen's lack of freedom in who she chooses as a husband