The highwayman is a slight variation of the standard bandit. Highwaymen have the same loot, equipment, and stats that regular bandits do.
Highwaymen are Khajiit two levels above the Hero's own, who will often hide near one of the great roads and jump out as they pass, demanding a toll. If not paying, they will attack. None of them will be that difficult to defeat, however, as they usually travel alone. They can also be easily avoided by speeding past them on a fairly quick horse, such as Shadowmere.
Another way to deal with them is to pay the toll of 100 then, when he turns his back, power attack him, although this will count as an assault. Once paying up, one can talk to him as to any non-hostile NPC. However, should they leave and return he will again demand gold.
The last option is to plead poverty if the Hero has less than 100 . If they wear clothing that is extremely poor in appearance or not wearing clothing at all, the highwayman will leave them alone. If they are a vampire of a level of at least 50%, even though a highwayman may approach them, he will react with fear like many other Characters, rather than demand money.
"This is a hold up. Hand it over or die.
- [Pay 100 gold] "You're smarter than you look."
- No. Take it from me if you can. "We can play it that way if you like."
- "Pay up, or else." – When approached
- "Good choice." – After paying
- "Thanks. Until next time, ha ha ha." – After paying
- "Easily done." – If refused to pay
- "Actually, that's the way this one prefers it." – If refused to pay
- This list is incomplete; help us expand it.
- Outside of Fort Ash.
- At the south end of the Gold Road between Anvil and the Brina Cross Inn.
- On the long bridge on the Red Ring Road at the southeast corner of Lake Rumare.
- On the Gold Road just east of Skingrad.
- On the Yellow Road between the Panther River and Corbolo River.
- On the Red Ring Road on Pell's Gate's side of the Old Bridge
- Despite the shirt's name, "Highwayman's Shirt" does not appear on any highwaymen.
- When wearing the Gray Cowl of Nocturnal, he will say what any thief will say and will not ask for a toll.
- If paying the 100 , one can pickpocket the highwayman for more and a lockpick or two.
- If one decides to pay the toll and sneak attack the Highwayman thereafter, one can reacquire stolen money without risking a fight.