Are you looking for Skyrim quests that drop great loot, take you far off the beaten tracks to weird and wild places? We've compiled a list of some of the most compelling and interesting quests that give you the best loot and adventure.
Innocence Lost - The Dark Brotherhood - Windhelm
On your travels through Windhelm, you'll find yourself in an alley where two people will be standing outside a house where they're discussing the rumor that the young boy who lives inside is performing the Black Sacrament (the ritual to contact the Dark Brotherhood assassins to make a contract).
If you pick the lock to the house, you'll find a young boy who ran away from the orphanage in Riften because the mistress was abusing the children. He believes you are an assassin from the Dark Brotherhood who has heard is plea: kill Old Grelod and release the kids from her tyranny. Take the old bag out, and sleep well that night with the young man's (worthless) heirloom as payment and you'll discover you've stolen a contract from the Dark Brotherhood.
Blindsighted - The Thieves Guild - Riften
You've discovered that Thieves Guild head honcho Mercer Frey has been filtering off the Guild's hard earned funds for years. You find out he has also stolen the Key of Nocturnal — a lockpick that will never break and makes plans to leave Skyrim a rich man to whom no lock is impenetrable. You track Frey down to ancient dwarven ruins, which contain the legendary treasure 'The Eyes of the Falmer'.
As you progress through the ruins and avoid his cleverly placed traps, you'll face off against Frey to make him pay. Easier said than done, as he has invisibility spells and is a fast little son of a gun, landing hit after hit if you're not prepared. Killing him will cause the ruins to collapse, but you'll manage to escape with the Key of Nocturnal and the Eyes of the Falmer, and you'll be rewarded with being the new guild master. Whether the Key of Nocturnal happens to be returned to where no man should ever find it again immediately is up to you... Drop the Eyes of the Falmer off to Delvin in the Thieves Guild for a large cash reward.
To begin the Thieves Guild questlines, enter the Riften marketplace during daylight hours, and you'll automatically be approached by Brynjolf who offers you a tempting proposition and gives you an opportunity to test out your pickpocketing skills.
The Book of Love - Riften Side Quest
Love in Skyrim is not bound by race or gender because the people find life too short given the constant fighting. If you want to get married, you'll first have to visit the Temple of Mara in Riften and speak to Dinya Balu, asking for the Blessing of Mara. In order to prove yourself worthy of the Blessing, Dinya sends you on three quests to spread the message of love around Skyrim. Your first stop is to a woman in Ivarstead who finds herself caught in a love triangle that needs solving.
In the second quest, the court wizard Cancelmo is attracted to Faleen in the Jarl's court, but doesn't know how to talk to women. For a fee of 200 septims, a local lothario will adjust one of his poems so you can pass it off as a declaration from Cancelmo. After taking a letter back to him, you can witness his bumbling confession in person. Last you must reunite two lovers both beyond the veil of death. Put on the amulet that you're given and head to Rorikstead, where you'll find a spirit looking for the body of her husband. After finding her husband off to the Northwest, you can lead him back to his waiting spectral spouse, where they declare their undying love for each other and ascend skyward.
Returning to Dinyu Balu gives you a permanent +15% Magic Resist Agent of Mara blessing on completion, and you can get an Amulet of Mara which when worn will open new dialogue options for characters you can marry.
Forbidden Legend - Side Quest
This quest can be found a couple of different ways. You could find a fragment of the Gauldur amulet, read a book called Lost Legends found in Maven Blackbriar's house, or stumbl into one of the locations in which the quest takes place (such as Sarthaal, which you'll enter as part of the Mages College quest).
In ancient times, three brothers stole and divided up their father's powerful amulet, which caused chaos and saw them being chased into separate nordic ruins to their end. The Dragonborn will travel across Skyrim to different Nordic tombs, retrieving a piece of the amulet from each. Once you have collected the three pieces, you have to fight all three of the ghost brothers. When you have defeated them, their father banishes them and grants you the reforged amulet which grants +30 to health, magicka and stamina. You'll also pick up some pretty cool weapons dropped by the brothers too.
At the Summit of Apocrypha - Dragonborn DLC quest - Solstheim
As the final quest in the Dragonborn questline which takes you to Solstheim, you finally face off against Miraak, the first Dragonborn who is able to manipulate the will of dragons. In this epic closing quest, you'll ride a dragon to where Miraak is waiting, where you're in for a hell of a fight. Miraak has a lot of health, and once he's taken enough damage he'll become etheral and summon three dragons overhead. He'll use them to restore his health, so you'll have to defeat the dragons before you can beat him. On death, you can loot his corpse for unique armor, and his mask which grants +70 to Magicka.
The Whispering Door - Whiterun
The Whispering Door is a secret door tucked away into the bowels of Dragonsreach in Whiterun. You'll have to have reached level 20 before the innkeeper at the Bannered Mare will tell you about how the Jarl is having some trouble connecting to one of his children. His child has been in communication with the Whispering Door, which tells him the truth and history of the castle.
When you approach the door, it tells you that you're a more worthy champion. Steal the key and open the door to be greeted by Deadric god Mephala, and the Ebony Blade. The blade needs to be 'recharged' to restore it to it's former power, and the only way to do that is by killing someone who trusts you. You can tell someone trusts you when they talk to you more specifically, such as "You and me, we're the only two people around here who aren't complete fools", or you could grab your housecarl or spouse and kill them at home away from prying eyes.
Dragonslayer - Main Quest
The end is in sight. The Dragonborn has chased Alduin back to Sovngarde, the heavenly realm where all the sons of Skyrim go when they die. The first part of the quest will see you helping the Heroes of Sovngarde clear the mist Alduin has conjured. Once this is clear, you'll face off against the Bane of Kings one final time in a grand heavenly arena. The fight is made easier if you use Dragonrend on him, keeping him grounded, and if you're able to stun him, even better. When he's dead, you'll find yourself back at the Throat of the World, the summit of High Hrothgar. If you didn't kill Parthunax, he will be waiting for you and tell you that without Alduin, he should now be able to lead any last dragons away.
The Cure for Madness - Dark Brotherhood
The history of the Dark Brotherhood dates back many many hundreds of years. They worship Sithis, the entity of chaos and entropy, and revere the Night Mother as their spiritual leader. The pleas of those who perform the Black Sacrament, the ritual to call the Dark Brotherhood to service, are heard by the Night Mother who then passes on the contracts to her Listeners. The Listeners then hand the knowledge to Speakers who send Silencers to do the deed.
It's convoluted, certainly, but all you have to worry about is carrying out orders for now. This far along the Dark Brotherhood questline, you'll have become a Listener, having hidden and conversed with her in the Night Mother's coffin in surveillance of her Keeper, Cicero. You've learned that Cicero is weird, mad or both, and he's a potentially deceitful little beggar. After having found his journal detailing how he's been picking off members of the Dark Brotherhood, you hunt him to his retreat. Astrid, the leader gives you an awesome horse, Shadowmere, to use on your cross country travel. Why is he so cool? Well look at him...
Diplomatic Immunity - Main Quest - Solitude
This quest is where we begin to get into the politics behind Skyrim, and it's not as simple as Stormcloacks versus Imperials.
The Thalmor, a group of elven supremacists who claim to have single-handedly closed the Gates of Oblivion (which is only partially true) seek to unify the lands of Tamriel under one government, but in doing so want to ban the worship of Talos as it goes against their own principals which isn't going down well in Skyrim. The Thalmor aren't great guys, they think the lands should be racially cleansed of the inferior humankind, and don't take sides in the wars they provoke — instead, letting the warring factions demoralize each other so that they'll just surrender to the Thalmor's wishes.
Delphine, the Grand Master of the Blades, an secret ancient group whose job was to fight dragons, suspects that the Thalmor, are behind the dragons return to Skyrim. She sends you to infiltrate their Embassy in Solitude; there you'll meet Delphine who gives you your invitation and a change of clothes worthy of high society, and find Malborn who is your mole. Give him anything you want to sneak into the Embassy because you won't be able to take your gear with you. Some good items to take other than your usual weapons would be potions, soul gems and lockpicks.
Head to the Blue Palace within Solitude's walls and speak to the guard at the door and give him your invitation, inside you'll find Skyrim's upper crust society. After making polite small talk with a few guests, speak to Malborn at the bar who will tell you to cause a distraction so you can slip away and hunt for information on dragons. Speak to some of the guests and one of them will happily aid you in your cause.
While he's making a scene, Malborn ushers you out of the room where you can pick up the gear you had dropped off with him earlier. You're then entering forbidden territory, so you'll be attacked on sight by Thalmor Soldiers and Wizards. Make your way to Elenwen's Solar where you can hunt for information. You discover that the Thalmor are not behind the dragons return, but they do have information on someone who was thought to be long dead.
The only way out of Elenwen's Solar and out of the Embassy is through the tunnel in the back. The key is found on one of the Thalmor soldiers who enter behind you. Unlocking the tunnel and escaping into Skyrim allows you to travel back to Delphine in Riverwood and discuss the things you have learned.