Bounty of 1000 gold in all nine holds
There are nine holds in Skyrim, of which there is either a major city or a major town, these are:
Dawnstar (The Pale)
Riften (The Rift)
Markarth (The Reach)
Basically, just head into each of those towns and cities and cause as much mayhem as possible… You’re best creating a save (once you’ve been to all 9 cities so you can fast travel) and heading to each town and killing as many people and guards as possible – 1 guard should do it, but if for some chance they don’t react when you hit/shoot them, then attack a civilian first.
When it’s at 1,000, run to somewhere you can fast travel and then nip to the next city. Pack plenty of stamina potions/and or get a horse and when escaping, head for the water (unless you’re on a horse) – the guards seem to be scared of it! Rinse and repeat till all nine are done. Fun trophy this one.