The most significant example of freedom coming as a result of not listening to the dictates of society comes in Huck's decision to help free Jim from captivity on the Phelps farm.
When Jim is sold by the Duke and Dauphin to the Phelps family, Huck is alone for the second time in the novel. He is beset in his isolation by the moral dilemma that has been with him since first meeting Jim on the island - to acquiesce to society's moral perception of right and wrong or to follow his own conscience and free himself of society's dictates.
Huck chooses to think for himself and free Jim. His decision is one of freedom and marks, arguably, the moment of his greatest freedom in the text. Huck is willing here to "go to hell" to align himself with friendship, accepting the notion that this will lead him to commit a crime.
For Huck this is not simply a "technical" or purely legal issue. The crime of freeing Jim is a moral issue and even a religious one. Yet, he pursues freedom for Jim and for himself as he chooses to think for himself and to act on his own sense of what is right and what is wrong.