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5 Best Skyrim Quests: Amazing Quests You Should Do On Your Next Playthrough

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The Elder Scrolls V: Skyrim certainly has a vast variety of unique and interesting quests for you to gleefully discover and play through while spending your time in the bucolic landscapes of Skyrim. Of course, you may want to prioritize completing quests that have a lot of fan-acclaim for their storyline or the rewards that the particular quests may reward you with. This list will compile 5 of the best quests within the experience for players to take their time with and enjoy playing through.

Best Skyrim Quests — It’s Time To Adventure!

The list is compiled from community thoughts and personal experiences. The best Skyrim quests are:

  • A Night to Remember
  • The Dark Brotherhood Questline
  • The Mind of Madness
  • Awakening
  • Black Book: Filament and Filigree

Continue reading for more information on each quest.

A Night to Remember

Whether you are in the middle of treasure hunts or are simply trying to explore all of the caves in the land. You should absolutely try and seek out this quest that will be available from when you reach level 14 in the game. You will be able to find a person named ‘Sam Guevenne’ at any of the taverns in Skyrim randomly. When you meet him, simply chat with him and proceed with the quest.

There will be a lot of strange occurrences that happen in the quest and there’s a lot of humility attached to it so you will certainly find the humorous side of it if you enjoy the dialogue and events. In order to not spoil the quest, the main feats of the quest will not be discussed here.

The Dark Brotherhood Questline

Although not specifically one individual quest, the Dark Brotherhood quests are extremely fun and a bunch of them could certainly all end up on this list in their own right. The questline is executed perfectly and ensures that there is player retainment throughout the entire questline. So much so that you’ll probably find yourself going through the full questline with immense speed one quest after the other due to its brilliant nature.

Of course, to start the questline you can hear some rumors from any innkeeper and then can visit Aventus Aretino in Windhelm who will start The Dark Brotherhood Questline. After completing the first quest and receiving a note from the brotherhood, after sleeping in a bed for some time, you will be transported to an area that is a test for The Dark Brotherhood initiation. The full questline is a joy to experience. Plus, for completing the questline, you will reap a bunch of great rewards and throughout it, you will even get a fancy set of Dark Brotherhood armor, ideal to stylize your character with while making sure all of Skyrim will recall your name as a whisper in the shadows.

The Mind of Madness


This particular quest will reward you with one of the most exciting weapons in the game and that is the ‘Wabbajack’ weapon that can unleash a variety of random effects on whatever you hit. Not only that, the quest includes Sheogorath as one of the main characters for the quest.

All the cheese you could ever want will be in wait with a great feast and banquet on the table seen in the otherworldly place that the quest will transport you to. It has a lot of mechanics that keep things interesting and differentiates it a lot from the other quests in the experience. It can be started in Solitude and you will be speaking to a man named Dervenin and you will find him walking about in Solitude as shown in the image. This quest can then be started and you will be no doubt taking part in the thrills of this quest in no time!


Everyone likes a good vampire story and with the Dawnguard DLC, vampires you will certainly have! The Awakening quest will see you entering a great crypt with an atmosphere that is sure to make your blood chill softly on the frozen streams of tears that flow as you uncover what happens at the end of the crypt. You will be meeting an excellent character near the end of the quest and thus many players will value this quest with great significance throughout many of their playthroughs.

Level design and architecture are seen to an excellent standard as always within the experience and going through the areas for the first time and observing everything this quest has to offer you will always be a welcome addition to the game.

Black Book: Filament and Filigree

The Black Book: Filament and Filigree quest is from the Dragonborn Expansion and when you encounter the quest by reading the Black Book you will be transported to a place named ‘Apocrypha’ where Hermaeus Mora’s influence wraps tightly around. An expansive green sea will be seen waiting before you with incredible enemy creatures scattered throughout. It furthermore can be a challenging environment to traverse at times which adds to the great enjoyment of the quest as you are making your way through the realm.

There are a number of Black Books that will take you to Apocrypha and every time you will be wanting to see more and more of the place for its excellent design and lore surrounding the area. References to the Black Books are heard a lot throughout the story of the expansion so actually getting to delve into the books and behold the spectacles that await your character within them.

That is all of the Skyrim quests for this list! There are, of course, many more that can make their way onto the list but these are the five that you should seek out and complete if you’re wanting a brilliantly unique experience throughout your next playthrough as always. So time to sit the new fishing experiences to the side for a second and enjoy these quests.

The Elder Scrolls V: Skyrim is now available for PlayStation 5, PlayStation 4, Xbox Series X/S, Xbox One, Nintendo Switch, Xbox 360, PlayStation 3, and PC.

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Gordon Bicker
Gordon is a contributing writer for Attack of the Fanboy, a Games Design (BA) Honours student, and a Video Game Ambassador. He has been writing at AOTF for over a year and a half, with four years of games writing experience for outlets like Green Man Gaming. When he's not busy, he'll no doubt be experiencing games, writing poetry, playing guitar, adventuring, or happily starting a new Skyrim playthrough! As an avid Final Fantasy XIV player, he also hopes that you'll gain a warm feeling from his community stories. Gordon has reported on Fallout 4 and Destiny 2, whose favorite genres include action RPGs, MMORPG's and First Person Shooters but is always experimenting with many other types of games.