WARNING: SPOILERS
The Thieves' Guild is exactly as the name implies: a guild of thieves. It is called The Ragged Flagon and is based in the Ratways, a series of underground tunnels underneath the shady town of Riften. The leader of the guild is the guild master and is initially a man named Mercer Frey. While the guild technically conducts illegal operations, they are formally recognized throughout Tamriel and are considered a sort of "crime regulation," as they don't allow competition to occur. Also, as with any group of professionals, they have their own code to not rob each other or the poor or kill the ones they steal from. Despite all this, they still have a very powerful influence with the power to bribe guards and numerous contacts and black market dealers scattered across Tamriel.
The quest to join the Guild begins when you meet a man in the central marketplace named Brynjolf. He will ask you to steal a ring from one of the vendors, kept in a strongbox in his stall, and plant it on one of the other merchants while he creates a distraction. After completing his assignment, he will give you your reward of one hundred septims and instruct you to find him in the Ragged Flagon. Here, he will give you your next assignment: collect the debts that people in Riften owe the Guild through intimidation. Completing this task will gain entry into the Thieves Guild.
The next job you receive, given to you by the guild master himself, requires you to infiltrate an estate belonging to a former business partner of theirs and burn down three beehives. Then, sneakily make your way into the building itself and obtain the key to his safe and retrieve the bill of sale for the estate. Return to Brynjolf once this is done. He will tell you to find Maven Black-Briar, owner of the Black-Briar Meadery and long-time dealer with the Thieves Guild. You'll find that she wants her competitor, Honningbrew Meadery in Whiterun, put out of business. Talk to Maven's contact in the meadery who will inform you that the owner plans to hold a tasting for a person of high importance and poisoning the vats of mead will almost assuredly put her out of business. Report back to Maven and Brynjolf, telling you to speak to Mercer.
The guild master has found that the sigil on both the bill of sale and a note found in Honningbrew both belong to an old corroborator, an Argonian named Gulum-Ei. However, in order to get the information from him, you must steal a bottle of Firebrand Wine for him. He tells then you that a girl gave him a large sack of septims for the sale of the estate. Suspecting he knows more, you must follow him through a warren tunnels in Brinewater Grotto until you finally confront him for more information. He gives you the name of the one you seek; Karliah, the thief who murdered the guild master before Mercer, Gallus. Return to Mercer and tell of your findings, which Mercer will use as a basis to infer her location: Snow Veil Sanctum. You and Mercer will make your way through the labyrinthine ruin towards her location. Upon coming across a Nordic puzzle door, Mercer will open it by exploiting a weakness in it. Enter the door, upon which you will be shot with an arrow by Karliah. You will then witness a brief exchange between Mercer and the thief, after which Karliah will disappear. Mercer will then come up to you, vocalize a few parting words, then proceeds to stab you, causing you to black out. You will then awake outside of the ruin with Karliah in front of you. She will explain that the arrow was meant for Mercer, but instead was shot at you, tipped with a paralytic poison that slowed your heart rate and prevented bleed-out from the stab wound. She'll give you Gallus' encoded journal and direct you towards Enthir at the College of Winterhold to decode it.
Enthir identifies the text as the language of the Falmer, but isn't fluent in the language. He says you will have to seek Calcelmo in Markarth and acquire the key to the Dwemer museum and create a rubbing of the knowledge he will refuse to give you. After obtaining the rubbing, return to Enthir who, with Karliah in the room, will confirm that Mercer violated the sacred shrine to the Daedric prince Nocturnal known as the Twilight Sepulcher, something the Nighingales (sentinels of Nocturnal) are supposed to protect. In order to figure out what he's planning you must infiltrate his residence of Riftweald Manor, retrieve his plans, and return them to the Flagon's cistern where Karliah and Brynjolf await. The three of you will meet by the shadow stone in Riften, where Karliah will proceed to show you into the Nightingale Hall. You will obtain the armor of the Nightingales and proceed to the shrine in which Karliah will summon Nocturnal and induct you and Brynjolf into the Nightingales. This will prepare you for the ultimate challenge: killing Mercer Frey.
Before your expedition to Irkngthand, Brynjolf will inform you that Karliah has chosen you as the next guild master. Accept and listen to his instructions on following Mercer, who plans to make off with the Skeleton Key (Nocturnal's artifact) and steal the Eyes of the Falmer from the statue in the Dwarven ruin. You will face him in the sanctuary, where he will turn Brynjolf against Karliah for the entirety of the fight and will periodically turn invisible while fighting you. Kill him and take the Key and the Eyes off his body. The ceiling of the chamber will collapse, flooding the place with water. However, everyone is able to escape through an opening at the top of the chamber. Karliah will give you her bow as a reward and return to Nightingale Hall.
Your final test is to return the Key to the Ebonmere, a sort of portal to Nocturnal's realm of Evergloam. It resides within the Twilight Sepulcher, through which you will be put through a series of five tests. Upon entrance, you will meet with a sentinel, who reveals himself to be the spirit of Gallus. He will tell you to follow the Pilgrim's Path to reach the Ebonmere. The tests are as follows:
"Shadows of their former selves, sentinels of the dark. They wander ever more and deal swift death to defilers."
Sentinels will attack you if disturbed.
"Above all they stand, vigilance everlasting. Beholden to the murk yet contentious of the glow."
In a room with complete light and complete shadow, stay in the shadow at all costs. Light will damage your health while bathed in it.
"Offer what She desires most, but reject the material. For her greatest want is that which cannot be seen, felt or carried."
Extinguish the torches next to the statue of Nocturnal in the room.
"Direct and yet indirect. The path to salvation a route of cunning with fortune betraying the foolish."
You have one of two options: go down a hall with two dart traps, a pendulum trap, a spear trap and a battering ram trap or pick a master lock and face two sentinels beyond the door.
"The journey is complete, the Empress's embrace awaits the fallen. Hesitate not if you wish to gift her your eternal devotion."
Jump down the well and insert the Skeleton Key, which will give you access to the Ebonmere. Nocturnal will appear and "congatulate" you. Choose one of three gifts she grants you by standing on the corresponding platform.
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