Firstly, the title of this one should be "Chester's Trail" as he had first dibs on it and the episode is more about him than about Quint. Chester offers to help a family get to a Nebraska fort where they can become part of a wagon train to Oregon after they've been cheated by a phony wagon master. Nobody thinks he's capable of leading a wagon that far into Nebraska territory. He's clearly hurt by the lack of confidence his friends have in him. Instead Quint is chosen to lead the wagon, resulting in a dull sub-plot about the family's randy daughter who has her eyes on Quint. Meanwhile Chester decides to go after the phony wagon master and get the family's money back. He finds the man and plays rough with him, roping the guy and dragging him. He gets the money and brings the guy back to the marshal, then beats the wagon to the fort through a shortcut he found to give the money to the family. He rides back to Dodge with Quint, having earned everybody's respect.
When I first saw this episode some years ago, I was surprised to see a more dynamic than usual Chester. Now that I know the backstory- that Dennis Weaver wanted to leave the show and that this was one of the last episodes he was in, (there were just 7 to follow), it seemed to me that this represented an attempt by the producers and writers to entice Weaver to stay by turning Chester into a more impressive character. If I'm right about that, it obviously didn't work.
When I first saw this episode some years ago, I was surprised to see a more dynamic than usual Chester. Now that I know the backstory- that Dennis Weaver wanted to leave the show and that this was one of the last episodes he was in, (there were just 7 to follow), it seemed to me that this represented an attempt by the producers and writers to entice Weaver to stay by turning Chester into a more impressive character. If I'm right about that, it obviously didn't work.