Lyric discussion by DodgerFuckYou 

Cover art for The Highwayman lyrics by Loreena McKennitt

A lot of people seem to misinterpret the penultimate verse as indicating that the highwayman just immediately charged the redcoats and got himself killed.

That doesn't make sense if you pay attention to the timing. Instead, he makes the best of Bess's warning and gives them a good chase, but find out what happened later and returns to take his revenge. He's not a fool. He's just enraged.

First off, he doesn't even know Bess is dead, right away, just that a shot gave the redcoats away. "He turned; he spurred to the Westward; he did not know who stood bowed, with her head o'er the musket, drenched with her own red blood!" So when she shoots herself, he only hears the shot and takes off.

"Not 'til the dawn he heard it, and slowly blanched to hear." The Highwayman find out that that's what that shot is the next morning, through some undescribed rumour. We don't have an exact setting, but based on Noyes' experience and that he grew up in Wales, picking West Country, England as a setting seems reasonable. That gives a place to the West to go, still. Anyway, using these estimates, in winter, the sun rises around 7:30am in West Country in December (the story is set in the winter, I assume, from both the blustery weather and the fact that the hauntings at the end take place specifically in winter).

So that leaves our timeline as: Sunset, 4pm, the King's men arrive and tie up Bess. Eight hours of struggling (hours they went by like years) gets her to the point where her finger is on the trigger at midnight. She ceases struggling, to avoid alerting anyone, and waits. When she hears his hoofs in the distance, she shoots herself and warns him. He flees "to the Westward". Then at sunrise, hours later, he hears what happened. "Not 'til the dawn he heard it, and slowly branched to hear." Someone told him that Bess shot herself and is dead. That's what that gunshot was. He's furious and races back. But that takes four or five hours.

He then faces them in battle. It could be right outside the old inn, but we don't know for sure. It's four and a half hours later, though, and he's been riding hard. I must assume he did hais fair amount of damage. He's no slouch. He's got pistols, he's got a rapier, and he knows how to use them both. I even like to think he would have survived if he hadn't been so worn down from riding and lack of sleep.

I am, in fact, convinced that he does a great deal of damage. Maybe even nearly wins. Before he's shot down, his boot spurs are bloody. This may be from driving his horse so hard but I like to think it's from the blood that splashes onto him in the ensuing melée. It's a gory scene, I think, with a lot of dead soldiers.

Of note, I think we can safely assume that he at least got justice on the particular soldier who tied Bess up and told he rto "keep good watch," because Noyes refers to him as "the dead man". This guy, at the very least, is not making it out of this story alive.