Tim meets his cousins, the Platts, for the first time. Four girls sleep in a tiny clapboard house and the two boys sleep in the barn. Tim feels grateful to have grown up in the tavern, which always had plenty of room for himself and Sam to sleep comfortably. In a cozy scene, the Platt family, Tim, and Father sit around a fireplace. Tim observes that he felt shy about meeting them, but they do not feel shy, because they are in their house. Mr. Platt and Father discuss the disintegration of law in many of the colonies, the threat of the cow-boys, and the open hostility between Tories and Rebels. Father defends Redding, saying that law and order still reign. Tim falls asleep and is soon taken up to bed by his cousin Ezekiel. The two boys speak of the war. Ezekiel criticizes Sam for joining the Rebel forces, and Tim stands up for Sam. Ezekiel asks Tim which side he would fight for if he had to, and Tim replies, "The loyalist, I guess." As he falls asleep, though, he imagines the horror of finding himself pitted in battle against Sam.
Father and Tim leave early the next morning and have no more trouble as they approach Verplancks Point, thanks to escorts along the way. Tim is impressed by the size and beauty of the Hudson River, and astounded when they arrive in Verplancks and see the widest part of the river and the fisherman in their skiffs. He watches the fishermen with interest but sees that they look dirty and exhausted by the end of the day. The trade is successful, and the Meekers spend the night in a tavern before continuing on their way home. They plan to take a long, safe way home, but snow begins coming down and they know they must get themselves and their oxen home as soon as possible. The oxen are already uncomfortable, slow and bawling from the snow, so Tim and Father stop finally to stay the icy night with the Platts.
When Tim and Father depart from the Platt house, the snow has covered the land and the ground is slippery and hard to travel. Their escort home has not met them, due to the heavy snowfall. They trek on, Tim behind with the cattle and Father riding ahead on his horse to check on the safety of the road. Tim feels frightened and lonely, but he keeps going. The Meekers make it through Ridgebury with no problems. But they do not feel entirely safe yet, and Father rides up again to scout the path ahead. He takes longer than usual, and Tim passes the time by naming all of the countries in the world, stumbling over whether to count America, finally deciding not to. Tim begins to worry and think of possible reasons why Father has not returned yet, but he knows that none of his excuses are true. Tim tries unsuccessfully to speed up the oxen, then leaves them next to the road and jogs along, following Father's horse's tracks.
Tim comes to a space where the horse's tracks are surrounded and intermingled with tracks of many other horses and then trail away on the road. Tim knows instantly that Father has been ambushed by the cowboys. Tim prays, then panics, and runs into the woods to hide, trying to decide what to do. He wonders what Sam would have done, and concludes that Sam would do the brave, daring thing, which would be to rescue Father. It dawns on Tim that the bravest thing is not always the smartest thing, and he wonders what Father would do. Father would take the goods back home so that their tavern could make it through the winter. Tim runs back to the oxen and thumped them into motion.
As he moves along with the cart, he knows that the cow-boys will return, and slowly forms a plan for dealing with them. Night falls, and soon Tim spies three tall figures blocking the road ahead of him. Tim cries out, "Are you the escort? Am I ever glad to see you." The cow-boys ask what he means by talking about an escort. Tim feigns fearlessness and trust in them, and explains that his father called an escort in case the cow-boys came to harass them. The cow-boys begin to argue about whether to stay or leave. They want his goods, but they do not want to get ambushed by the coming escort. A dog barks, spooking them, and they flee. Tim begins to laugh and cry with relief and triumph. He has saved his family's goods, he has acted bravely and smartly, and he has a great story to tell Sam. He continues traveling through the night until he arrives home in Redding.
Tim travels a significant distance away from his home territory for the first time when he goes on the trip with his father. This distance allows him to gain some perspective and appreciate his own life. He sees his cousins, who must sleep in crowded rooms, and sometimes in the barn, and he feels grateful for having grown up in the tavern, with warmth and room to sleep comfortably. Tim finds himself standing up for Sam when his cousin Ezekiel criticizes Sam for joining the Rebel forces, even though Tim himself generally wishes Sam had made different decisions. Away from his usual context, Tim is able to define himself and his opinions by consulting the information he has gathered through new experiences. He recognizes that with his family position, he would probably wind up fighting on the Loyalist side, but he also recognizes that his loyalty to Sam brother makes him uneasy about shooting any Rebel, knowing that it could be his own brother, or anyone's brother.
At Verplancks Point, when Tim watches the fishermen, he has another experience of observing new surroundings and winding up being grateful for his own lot in life. The river is wide and sparkling with excitement, and Tim wishes that he could have the chance to live here and work as a fisherman all day on these waters. After watching the fishermen pull in their boats and sit cold, tired, and hungry on the shores, however, Tim realizes that their work is not as glamorous as it seemed initially. Tim begins to identify with his home, work, and family after thinking about it and choosing to do so, rather than unthinkingly, by default. This new thoughtfulness is one of the crucial elements of Tim's developing manhood. Chapter Eight marks a crucial moment in Tim's ability to assume control and responsibility for his life at home. Before the journey, Tim frequently had to make excuses to escape from his father's sight, whereas after the journey, Tim has to be in charge and figure out on his own how to face the reign of war as it closes in upon his town.
Chapter Nine examines the opposing influences of Sam and Father on Tim. While Father rides up ahead and Tim leads the cattle alone, he passes time by naming all the countries in the world, a game that reveals his thought process. Tim acknowledges to himself that if the Rebels win the war, America will be a country, not a colony. Then, however, he thinks of his father's certainty that the Rebels will lose, and so he discards America as a country. This thought process is typical, for Tim often thinks first of Sam's opinions, and then of his father's.
When Tim realizes what has happened to his father, he considers what Sam would do and what his father would do. Tim wants to act bravely, as Sam would, but then he makes the important distinction between being brave and being smart, and he does what his father would have wanted. Although he is influenced by his father, however, Tim forges a solution to his problem using cleverness and ingenuity that are solely his, and not based on Sam or his father. Mr. Meeker speaks evasively and stubbornly to the cow-boys on the journey out, so we can assume he would spoken in the same way on the journey back. Sam would have risked his life to save Father, perhaps getting killed in the process and almost certainly losing the cattle. Tim does neither of these things. When he reads the tracks and instantly understands the situation, it is a turning point. His intuition sharpens, and he begins to come of age. He seals this step in his maturation when he lies easily to the cow-boys, outsmarting them and arriving home safely with the supplies. The cattle trip begins as an exciting adventure, but it turns into a frightening and test of manhood. Tim succeeds by facing the cow-boys just as resourcefully as an intelligent, experienced adult could have hoped to do. Tim's life has lost its playful, imaginary element. He is done with trying to sneak away in search of stories to tell Sam. Without looking for excitement and danger, he has found both. Although it makes him proud to have triumphed, Tim now sees firsthand that the dangers involved are hardly worth the risk.