Partridge is shocked to hear that Allworthy banished Tom, since he truly that Tom is Allworthy's own son. He secretly believes that Tom ran away from home, and begins to devise a plan to send Tom back to Allworthy so that he can, in turn, be restored to Allworthy's favor. Jones has bonded with the landlord, who is bed-ridden from gout, over horse-racing. This man spends much of his time fighting with his wife, who constantly invokes her first husband. Tom and Partridge leave for their expedition. The landlady does not condescend to say farewell.
Tom Jones and Partridge head for Gloucester and, on arriving there, decide to lodge at the Bell, which the narrator recommends to his readers. The landlord's wife, Mrs. Whitefield, is beautiful and good-natured and generally free of silly notions. She notices "in the Air of our Heroe something which distinguished him from the Vulgar" and invites Jones to dine with her that night. At dinner, Jones meets Dowling, the attorney from Salisbury who conveyed the news of Mrs. Blifil's death, and a petty-fogger, a term for a lawyer willing to take any case. Displeased with the paltry conversation, Tom leaves the table as soon as the food has been cleared. After he has left, the petty-fogger proceeds to tell a distorted history of Tom's life. He claims that Tom is "the Bastard of a Fellow who was hanged for Horse-stealing." When the Petty-fogger says the man's name is "Thomas Jones," Dowling gets excited, saying he has heard about many good things about him. The landlady no longer likes Tom and refuses to drink tea with him. She is so rude to him that he pays his bill and leaves the house.
Tom and Partridge depart from Gloucester early in the morning. It would be dark if it were not for the full, red moon. Tom launches into quotations about the moon, but Partridge complains of the cold. Partridge wishes to return to Gloucester, since they are unsure of their route. Tom wants to go forward and Partridge is forced to comply. As they walk, Tom wonders whether Sophia might be watching that same moon. Tom asks if Partridge was ever in love. Partridge says not only has he experienced the enjoyments of love, but the nastiness too, for his wife was very unkind to him. Partridge says he knows a way for Tom to be in Sophia's arms. Tom claims that at present his greatest desire is to effect "a glorious Death in the Service of my King and Country." Partridge suddenly realizes that he and Tom are on opposing sides of the conflict—whereas Tom supports King George, he himself supports the Jacobite rebellion.
Tom and Partridge arrive at the base of a sheer hill. Through the trees on the hill, they see lights shining and approach to investigate. No one answers their knocking, but eventually an old woman appears at a window. Partridge promises her that Tom is a gentleman and she lets them in for half a crown. The woman, whom Partridge thinks is a witch, warns the men that her Master, the Man of the Hill, will be home soon and that he is a hermit who "keeps no Company with any Body." Suddenly there is hollering outside of the door and voices demanding money. Tom grabs a sword from the wall and scares some robbers away from the Man of the Hill, who was returning home. The Man of the Hill, at first suspicious, now calls Jones his "Deliverer" and "Preserver."
The Man of the Hill begins his history. Born in the village of Mark-in- Somersetshire in 1657, he is the younger son of a "Gentleman Farmer" and his "arrant Vixen of a Wife." The Man of the Hill's older brother cares for nothing but hunting. The Man of the Hill, however, advances rapidly in his studies and attracts the attention of learned men in the neighborhood. He is sent to Exeter College at Oxford where he meets a rich, debauched man called Sir George Gresham, who corrupts him. He becomes so rebellious that he is almost expelled by the vice chancellor. His father refuses to loan him more money, so he steals forty guineas from a friend. The Man of the Hill escapes punishment by running away with a lady to London, where he continues his wild lifestyle. This lady informs on him and soon he is thrown into jail, where he reflects on his behavior. He is allowed to return to Oxford, where he finds that his friend has dropped the charges. Partridge interrupts, telling a story about a man who was hanged for stealing a horse and came back as a ghost to torment the plaintiff.
The Man of the Hill continues his story. Now that he has ruined his reputation at Oxford, he returns to London. He has no money and no friends. One night he meets up with an old Oxford friend named Watson, with whom he eats and gambles.