The Highwayman rides his horse to go see the love of his life, Bess. She is the landlord's daughter, who also is in love. The Highwayman rode to the old inn door by horse.
The other ostler Tim, was eavesdropping on the conversation between Bess and the Highwayman. Tim is also in love with Bess. Tim was described as "dumb as a dog" because of the eavesdropping and his craziness. The snoopy, loser of a guy Tim goes and tells the red-coats about the conversation.
The kiss goodbye between the Highwayman and Bess was a romantic moment for the two. He kissed Bess's "sweet black waves" on her head. The Highwayman was saying goodbye because he was about to go rob somewhere, to get yellow gold. He also warned her that the law may harass him all day because of the act..He told her to wait for him until nighttime.
After crazy Tim tattled on Bess and the Highwayman, the red-coats showed up at the inn door the next day. There was still no sign of the Highwayman.
The men did not talk to Bess's father, but they drank his beer. The men tied up Bess to the bed after they entered the inn. It was now when the villains have been exposed. They set an ambush up for the Highwayman as they camped at the window keeping an eye out for him to come back, with their guns ready to kill him. This was Bess's "Hell at one dark window" because she could see out the window where her boyfriend will pass by.
Bess had eventually got loose of the rope, setting her free. To protect her boyfriend, she pulled the trigger and killed herself. The Highwayman heard the gunshots, so he went West. It was later until he found out that his girlfriend killed herself to protect him.