Please note I have tried to keep this completely spoiler free.


5. Waking Nightmare — Dawnstar

Travel to Dawnstar, and you will hear the townsfolk muttering about nightmares plaguing the village. If you journey to the inn, Erandur, a priest of Mara, will approach you and tell you that the village will slowly go insane if something is not done about the nightmares. Erandur will accompany you to Nightcaller Temple to right the wrongs. This quest is one of the more dramatic, and features some insidious forces at play.


4. The Mind of Madness — Solitude

If you explore Solitude, you will eventually come across a maddened beggar who is away from his master, and desperate to find him. This is a quest that is easy to write off as “not worth the effort,” but don’t be too quick to judge. The beggar will ask you to journey to the Blue Palace, and once you step into the Pelagius wing, what follows is a trip down the rabbit hole.


3. Laid to Rest — Morthal

In Morthal, you will see a house that has burned to the ground. Townsfolk will whisper that it is cursed and bad luck. If you speak to the Jarl about it, she will tell you that she has her suspicions of what happened, but that she needs you, an outsider, to confirm them. Easily one of the saddest quests available, it’s guaranteed to tug at your heart strings, and offer some very unique character opportunities.


2. The Black Star — Azura’s Shrine

There is little way to skirt around the fact that this is Azura’s quest. Travel to Azura’s shrine (getting there is half the fun), and the priestess of Azura will tell you that Azura foresaw you coming. She will offer a rather cryptic quest, saying that someone has attempted to turn a star black. Once again players will find themselves running around through dungeons and various cities, but the end of this quest is where the fun shines. Featuring one of the most unique locations in the game, it’s a fun ride in order to obtain the Best. Soul. Gem. Ever.


1. A Night to Remember — Whiterun

To say too much about this quest will spoil what is, unquestionably, the most entertaining and enjoyable side quest available. No, I’m not exaggerating. In Whiterun, go to the Bannered Mare and approach the bar. A man named Sam will challenge you to a drinking contest. Accept his challenge and down three of his “special brew.” What follows is a quest that will, quite literally, take you across the entirety of the map, as you try to retrace your steps from the previous evening. Just remember: tigers love pepper — they hate cinnamon.