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:
Falkreath (Falkreath)
Whiterun (Whiterun)
Morthal (Hjaalmarch)
Dawnstar (The Pale)
Winterhold (Winterhold)
Solitude (Haafinger)
Riften (The Rift)
Markarth (The Reach)
Windhelm (Eastmarch)
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.