How to Join the Dark Brotherhood in Elder Scrolls Skyrim
The Dark Brotherhood returns in Elder Scrolls V Skyrim! The Dark Brotherhood was one of the most popular factions featured in Elder Scrolls IV Oblivion. Joining the Dark Brotherhood in Skyrim is a bit different, but is somewhat similar.
There are technically a few ways to start this quest, but the city of Windhelm is where you will ultimately need to travel to start. Asking about rumors inside Skyrim Inns or Taverns may give you information about a boy named Aventus Aretino. One of the closest places to ask about rumors near Helgen is the Sleeping Giant Inn in Riverwood. Riverwood is marked on your map.
People in the Honorhall Orphanage in Riften will tell you about Aventus Aretino (the escaped orphan). They point you to Windhelm (where he fled).
How to Join the Dark Brotherhood in Elder Scrolls Skyrim (Innocence Lost Quest)
Travel to Windhelm. Windhelm is marked on your map. It is in the right eastern portion of the map, in the snowy region. Your objective is to find Aventus Aretino. The guard will tell you about a ritual going on in a house in Windhelm.
Find the Aventus Aretino residence. It is located in the right portion of Windhelm. You will see two people named Grimvar Cruel Sea and Idesa Sadri having a conversation about the ritual going on in the house nearby. Speak to them and they will tell you about a boy who is reciting the Black Sacrament.
Enter the house by lock picking the (novice) lock. Speak to Aventus. He tells you that he wants the headmistress of Honorhall Orphanage dead because of her violence toward the other children in the Orphanage.
Go to Honorhall Orphanage and speak to to Grelod the kind. After speaking to her, kill her when she sleeps (recommended). You will get a bounty if you don't kill her quietly.
Once she is dead, travel back to Aventus and he will reward you. Quest Complete!
Joining the Dark Brotherhood in Elder Scrolls Skyrim (sleep to start Dark Brotherhood quests)
Next time you sleep, you will be awoken in a shack. The Dark Brotherhood have been keeping an eye on you. An assassin named Astrid thinks you could be a good member because of your "previous murderous actions."