Highwaymen are Khajiits two levels above your own that will usually hide near one of the great roads and jump out at you as you pass, demanding a toll. If you don't pay up, 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 on you, power attack him, although this will count as an assault. Once you pay up you can talk to him as you could any non-hostile NPC. However, should you leave and return he will again demand gold.
The last option is to plead poverty if you have less than 100 . If you wear clothing that is extremely poor in appearance, or you wear no clothing at all, the highwayman will leave you alone. If you are a Vampire of a level of at least 50%, a highwayman will approach you, however, he will react with fear like many other NPCs rather than demanding money.
- This list is incomplete; you can help by expanding 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 you pay the 100 gold you can pickpocket the highwayman for more and a lockpick or two.
- After paying the toll, the highwayman will be non-hostile. Meaning you can ask him about rumors, but nothing else. Attacking him while he is like this will count as assault. If you return to that spot later, he will ask for another toll, the same way as he had before.