Pickpocketing is one of those skills which may not sound too attractive, yet it’s often one of the easiest ways to make money in Skyrim. As long as you have a high sneaking attribute you’ll find it easy to bypass lengthy quest-lines, poison foes and come across some really nifty easter eggs during your adventures by taking an unwelcome peak in civilian pockets.
The trainers listed below will help you in levelling up your characters’ pickpocketing attribute, but to further supplement your skills we recommend enlisting in the Thieves Guild in Riften to get some advice on how to utilise this skill properly.
Level: Adept (can train up to level 50)
Location: Ahkari’s Caravan which travels between Dawnstar, Whiterun and Riften
Extra Info: The khajiit caravans are very difficult to find as they move from city to city and stop occasionally to sell goods. Due to their roaming nature and the fact they usually only stop for a day or two before moving on we suggest not obsessing over these NPCs. However if you really want to see them, the best thing to do is fast travel to Whiterun, walk outside the city district, walk just outside of the walls and wait 24 hours until you see a camp form to the right. This can take multiple attempts, so don’t expect this to happen quickly. Alternatively, just keep an eye out for camps whenever you visit any of the above cities.
Silda The Unseen
Level: Expert (can train up to level 75)
Extra Info: She is easiest to find during the daytime as she doesn’t move around too much, however her location does change often in the city of Windhelm. Incidentally she’s also one of the three witnesses involved in the Blood on the Ice quest, but this activity only initiates once night has fallen.
Vipir The Fleet
Level: Master (can train up to level 100)
Locations: Thieves Guild HQ, inside the cistern room
Extra Info: This NPC is most easily found after you’ve been accepted into the thieves guild. Just head into the cistern room and you’ll see Vipir mulling around pretending to do things…
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