I am trying to complete the master criminal achievement and have a 10,000 bounty in all the holds but winterhold. What is the easiest way to gain a bounty in this loosely populated hold?

Murder a guard

It says 1,000 bounty, not 10,000.

well I guess I never learned to read in college. Thanks

The best way to do it is to get a horse, put it in the middle of town, kill as many people as you can then gallop away, thats what i did

If you don't want to kill anyone you could just transform into a werewolf.

Just remember, always leave a witness- kill the last one, and all your hard work goes "pfft".