Top 5 most enjoyable side quests in ‘Skyrim’

Azura Shrine 300x168 Top 5 most enjoyable side quests in SkyrimWith the plethora of quests available within the main story, and the various factions of Skyrim, it is possible for newer players to eschew the side quests and minor offerings. It’s true that a great many of these are your standard RPG-style quests in which you play a well-armored FedEx man (“I lost this item. Can you get it for me?”), but there is a great deal of fun to be had if you know where to look, and we’ve spent tons of time looking!

Aside from offering great opportunities to explore, level and line your pockets with epic loot, these quests can also help towards the purchase of a house (Most town Jarls will ask you quest for the people of the city to “establish” yourself within the city). Also, as mentioned in my review, you never know where you’re going to find a dragon word of power.

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.

About Jen Bosier

Jen lives with her husband, daughter and super-villain cats. If she's not reading comics or engrossed in a WH40k novel, she's probably telling you which horror games you should be playing. She's a recovering member of the PC Master Race, and a reluctant Xbox fangirl. You can also find her on the Furious Fourcast.


  1. These sound great!  Do the encounters scale with level or do I need to make sure I’m of a sufficient starting level to avoid having my ass handed to me on a plate?

    • Jen Bosier says:

      They do scale for the most part. The “Night to Remember” is easily the trickiest one due to a Pyromancer with a bad attitude. I tackled it at level 20 successfully. “Laid to Rest” will be the other very challenging quest, but I was able to knock it out around lvl 13-ish. :)

      • Groovy, thanks Jen.  Looks like I’ve got a ways to go yet.

      • The Laid to rest quest was a fun, yet saddening one. I tackled it with only the SLIGHTEST problem at around lvl 10… I was supposed to kill someone already but didn’t so she was a little harder to beat during the last part of the quest, but I prevailed and succeeded.

  2. In #Skyrim n 3h later..where I am?TheEXACTsamedamnplace:( @xSirMarkx hav u finished main quests?Im more interested in side quests

  3. I have to disagree with “A Night to Remember,” being a remotely good quest. It’s semi interesting, but prety non sensical and chaotic, and would be more fitting as a quest for Sheogorath instead of the guy who it’s actually manipulating the situation.

    Not going to reveal spoliers, but my main problem with this quest is that 1) It doesn’t tie up huge holes in the quests “Plot,” due to it being one of the dynamic quests that can have it’s contents being very different depending on a number of mostly unseen factors and 2) despite the dymanic features added, it doesn’t really vary the quest much, and no matter what the set up, makes your character do a series of horrendously stupid things. This would only be fitting for some mentally deficient Argonian who was dropped as a hatchling, or a pretty seriously “Bro,” Nord who for some reason, couldn’t hold down his liquor. 

    You end up going through such an innane trail, you have to ask yourself, “Why would my battle hardened, alcohol lead belly of a Companion Reguard actually get that wasted and do that many stupid things when only having 3 drinks?” Or… “Why would my newly appointed arch-mage Altmer have so little mental willpower, after mastering multiple schools of magic, to not resist some magic in this drink itself?”

    In the end, no matter what character you’ve envisioned, all characters you play will take similar (Yet slightly different) frat-boy worthy path of stupidity, leaving you confused and wondering, “Why the heck did the game just make my tempered, experienced Assassin act like a drunken 17 year old football player?”

    • Jen Bosier says:

      I think you may be reading too much into the quest. It’s meant to be a “Hangover” style frivolous romp as opposed to a major plot point. *However,* having said that, it is always interesting to read other people’s take on a quest. Thanks for your input! :)

    • Eli your forgetting that its Sanguine, a daedric prince. And that the “alcohol” was as he put it the good stuff which can lead to the conclusion that it might not be “human” alcohol but something on a whole new level. So with it being a daedric prince he could remove all the experience or skills that would prevent you from falling fool. I agree with Jen you seem to be reading too much into it though I am not trying to discourage you or put down your idea. Let me offer this, I agree with you that they should have filled those “holes”. Maybe Sanguine telling you that the drinks where powerful enough to strike even the most stealthy thief with a stagger or something like that. It should have had a little more something to it than you just being taken into the folly.

    • It’s magic man, not the booze itself. Have a sense of adventure! who was behind it the whole time explains everything. mortals are his playground!!! lol

  4. Linkmaster1991 says:

    I’m gonna be “That guy” and point out that none of these are side quests. They are daedric quests except Laid to Rest. I came here hoping to complete my sideways achievement having 30+quests done with only 6 side quests.

    • Jen Bosier says:

      To me, a side quest is anything that is optional, and does not affect the main story or any faction. There are numerous fun side quests for the Dark Brotherhood, but those are factional. I tried to go through and pick as many of the utterly frivolous quests as I could. True, most of those were the daedric quests, but that also deserves recognition over, say, Oblivion or Morrowind. The daedric quests have, historically, been a little hit or miss on the “fun” level. Sorry this wasn’t quite the guide you were looking for. :(

  5. Tigers love pepper? Hangover reference I guess? :P Btw, I’ve done “A night to remember”… I had no idea what would happen to me, a big viking warrior after 3 drinks but never underestimate a mysterious man with a hood in a tavern :P

  6. The Mind of Madness was probably the most entertaining Daedric Quest for me. I love Sheogorath. He was hilarious to listen to in Oblivion, and I was excited when they used the same voice in Skyrim.

    I like the fact that the Daedric quests aren’t just… find shrine, kill x target/find x item, return to shrine, get nifty item now like in Oblivion. When I did my first Daedric quest it almost suprised me because I had no idea it was coming up at all. Obviously a few of them are heading to shrines though. I was surpised to find that after i went through many of my quests, I had roughly 4-6 Daedric quests in my journal and I didn’t enen know it.

  7. Kaotictigress says:


  8. some I have done already, some i am busy with, these are/were fun quests. “The Mind of Madness” gave me quite a fright, was not expecting to end up where I did when I was just walking down the passage way and for “night to remember” that angry lady almost killed me, but mid fight I sort of went through the portal by mistake, so yeah hahaha

  9. the sanguine quest is the most enjoyable. more than sheogorath ones, i think

  10. Beau daniel says:

    The Night To Remember quest SUCKS. I just did it, it took about 15 minutes. The reward sucks, and I got bugged and trapped and had to reload a save. Its riddled with bugs.

    • WTF!!! Sanguine Rose is the BEST STAFF in the game. How does it suck? You can summon a Dremora. They are good fighters.

      • Well, arguably the best. Some people don’t like having people or summoned creatures follow them, and I’m begining to turn into one of those people. They just keep getting in the way.

  11. Rpg fanatic says:

    I’d just like to say that i agree with the above post in regards to these quests being absolutely great fun!  I know some might say that they don’t qualify as side quests due to the fact that they are daedric in origin (and i’m sure the purists will say that they aren’t side questse because they show up in more than just the misc section of the quest journal)  but jen is right when she says they are side quests (Don’t affect factions, main plot, side plots, etc….) and she is further correct in that they are frivilous fun romps that are purely for short story or reference kicks!  For all you haters of these side quests out there, you might want to try actually enjoying the references to movies, books, other games, etc that are found hidden in the many parts of Skyrim (there’s even a weapon that very closesly parralels an item used by a character in a book written way back in the 80’s lol…Amazing!)  and stop just relying of the pointless WOW grind…..this game isn’t about gear score (the thing that kills WOW late game) or tangible rewards its about the enjoyment of the full immesion into a multiverse that has been painstakingly created and added to since the dawn of Arena way back when.

    Thanks Jen for the great post!

  12. My balls hurt

  13. Kyle Epstein says:

    A Night To Remember sounds like The Hangover: Skyrim style. Down a crazy dude’s special brew, wake up miles away, and spend the next 2 days trying to figure out what you f*cked up while you were wasted. :D

  14. Side quests are ANY quest that has nothing to do with the main story. If the quest can be skipped and the game can still be beaten, then it’s a side quest.

  15. I literally finished this quest in 20 min and was like wtf I thought it was supposed to be some crazy amazing quest?

  16. i just want to know how the fuck you drunkenly sell a goat to a giant without being stepped on? lmfao

  17. Sounds really good!
    I’ve already completed the first 4 before reading this, but I can’t wait to do number 1!


  18. I don’t care wether its a side quest or not all I care about is wether it’s a good game and it is so I am happy :)

  19. i like just killing dragons at the word walls and after i keel em’ all i wait 48 hours then they all seem to appear again. :)

  20. *kill* sorry lol

  21. Ok im trying to get a night to remember quest and i cant find sam anywhere ive been to the Bannered Mare and he wasnt there :( i think i also checked the winking skeever i cant seem to find him i check every so often but hes not there im assuming maybe because im married to yosolda that quest may not be available to me anymore idk but im level 41 and still havent gotten it help if you can?

    • he spawns in the very first tavern you walk into when you start the game, if you went inside the riverwood tavern first before going to the bannered mare he’s inside the tavern in riverwood…etc. like instead of going to river wood on this new toon i made, i went to ivarstead first and now he’s waiting in the ivarstead tavern for me to eventually do that quest.

  22. skyrimnice says:

    the top quest i just skipped it all because i have 125 speech but seeing how fun it ‘supposedly is’ I am kinda regretting it. oh well don’t care.

  23. TheDoctorOfTamriel says:

    Technically all of these except “Laid to Rest” Are deadric quests and thus do not count towards your Miscellaneous Quest trophy/Achievement.

  24. Yes… Great list! I much prefer “A Daedra’s Best Friend” over some of these, but these 5 are still easily among my favorites… Hehe… Gotta smile just thinking about “A Night to Remember”. ;)

  25. I entered the blue palace and suddenly everyone started attacking me. But i cant kill anyone because they seem to be immortal and just go prone for 20 secs and then get up and start fighting again. Luckily im OP as hell and when everyone hits me i lose perhaps 2% of my total HP after 30 secs.

    I get through the talking with the npcs that gives me the key, even though i have about 10 immortal people hitting me with everything they got. I managed to pass the door but now i got that stupid imperial suck-up Jarl with me so i have to “kill” him every 20 secs. Finally i enter the teaparty and all the immortals have left me and i can carry on with the quest as it was intended.

    This is the most stupid shit ive seen in this game so far. SERIOUSLY BETHESDA! COME ON!!!!!!! WTF!!!!!!!!!!!

  26. a night remenber its not always in white run i saw the man in winterhold it depends on the game mostly its in dawnstar whiterun winterhold.

  27. So basically. . . just the quests that are finding Daedric Artifacts lol

  28. I couldn’t even find this Sam guy….

  29. The mind of madness quest was horrible. Only reason to do it for the Daedric Achievement. People keep saying A night to Remember was bad, I thought it was ok. But you get a GREAT STAFF. Sanguine Rose is the BEST staff in the game. You can summon a Dremora with it. They are tough to beat and can do a lot of damage(it varies based on your level).

  30. yea the sanguine staff is awesome i gave it to my follower and took most of her weapons so when ever we raid camps caves etc. we have like a team of dremoras the two that i conjure and the one she summons pretty funny seeing all them dremoras

  31. In response to Eli’s post… perhaps your hardened assassin should not have made the decision to enter into a drinking contest to begin with. I think that once you make that decision, you kind of forego the right (to some extent) to RP a character that values sobriety and the ability to choose their own thoughts and actions despite getting deliberately wasted. Besides, it seems the idiotic comic relief of the quest is the whole point for most players from the very beginning. Also, I think that while it would be nice to have EVERY quest perfectly tailored to fit the appearance, skills, and experiences of your character it would probably be a programming nightmare.

  32. Every one of these quests is extremely buggy. I have completed pretty much every major quest line with no problems, yet I have encountered at least one major bug on each of these quests, prevented me from completing most of them. Be warned

  33. Leonhart91 says:

    I’ve done all those quests, and they pretty much sucked. And the rewards sucked even harder.

  34. Leonhart91 says:

    Sorry if I sound overly negative, but this game is like a second Oblivion to me. The same weapons, same armor, and you get gold for almost every quest. ”Hey, thanks for killing the friggin dragon. Here’s 500 gold.”

    I’ll just continue exploring the equally boring crypts.

  35. Leonard91 says:

    I’ve done all of these quests, and they all suck. But then, so do most of the quests in Skyrim. Yeah, all you’re left with is a facsimile of Oblivion. I played until I was level 41, but I couldn’t go any further.

  36. i have finished 5-3 and activated 2-1 but haven’t finished them.

  37. Some quests are definitely better than others but if you smith daedric armors there’s no point except for fun. The mind of madness is really fun as for the black star is harder because you must kill strong dremora. A quest that is not up there is merhunes’ razor quest. You can loot lots of daedra hearts and leveled ingots. The reward is a dagger that has a chance to one hit k.o.

  38. Actually a night to remember begins at the inn you were near when hitting level fourteen for example mine started at the winking skeever in solitude

  39. Actually a night to remember can be found in diferent inns. For example mine was at riften

  40. Anonymous says:

    I think the Theives Gulid was the best :D

  41. Does anyone remember that hilarious Oblivion Sanguine quest? Where you go to the “fancy” parth, then use a spell that strips all the guests of their clothes? Rofl, love Sanguine

  42. Spencer says:

    I think a Night to Remember is probably one of the funnier quest because your going around fixing all the weird stuff and crap you did to people until you get to the thing you were going to marry I almost threw up then cut its head off

  43. Try Dead Space 2. Great horror game for this generation.

  44. lol i like how he quotes zach galifanckis at thee end there

    also azuras star, great quest.

  45. I think these are all really good quests, and all have interesting twists on the game. And really, none of skyrim is meant to be realistic. Since when have you ever met anyone that can speak three words and knock you backwards or pull a dragon out of the air, a DRAGON! This is a great guide, not quite the guide U was looking for seeing as I have done all of these on one account of another, but still these are really fun quests to partake in!

  46. So to all those people using the explanation that anything not affecting the main storyline is a side quest;
    First of all, completing the “main” quest line of this game hardly affects any of your actual gameplay ANYWAYS beyond a few characters and dialogue. Second of all, for the role players out there, completing all of the daedric quests may be their main quest. That being said, these are fun quests. I don’t see why anyone would say they suck, they’re a helluva lot more fun than digging around blackreach for a damn elder scroll. Btw, two more quests unmentioned so far I think, that are relatively amusing; the forsworn conspiracy. If you haven’t already done this one or have it in your quests, then, well, you probably haven’t really played the game. Also, I found the rescue mission given by that old greymane woman in whiterun is pretty fun. You fetan army of quest followers (well, 4), plus enough thalmor swag to drop a horse (including, I’m almost certain, a staff of paralysis which is always there, regardless of level). P.s. Don’t complete a night to remember, gleda=best follower evur.

  47. I liked blood on the ice

  48. The man at the bar isn’t there

  49. swags mcgee says:

    most of these quests can be done at lvl 15 if you have good sneak and a bow or magic i think i beat all but laid to rest because i don’t ever go to morthal

  50. A night to remember can be in any tavern- with me it was in the winking skeever in solitude

  51. EvilKrista says:

    I did the a Night to remember quest…it was fun..made me giggle…but when I got the ROSE…YES PLEASE…I’m an archer…I’ve got bound bow in my left hand and the rose in my right…best…char build…ever. Hello Dremora tank? Thank You.

  52. omg i cant do the mission because i have killied everyone in morthal there are no townsfolk or anything

  53. 1337h4xZ0r says:

    Completely off topic, collecting the crimson nirnroot out of the black reach is probably the buggiest thing I’ve ever found in sky rim, I hate , I have -18 nirnroot collected -_-

  54. I kind of like Ill Met By Moonlight because you can get both artifacts (Ring of Hircine and Saviour’s hide). Plus the Saviour’s hide looks REALLY GOOD on Aela.

  55. Hey everyone as of right now I am level 50 and I have completely all main quests and to many side quests and daedric quests to count I am looking for some secret quests or any interesting things to do in skyrim now?

  56. I dont care what anyone says i think my favorite part of Skyrim is when you kill alduin imanaged to do it lvl
    20ish. Im a heavy armored altmer sneak archer hard as hell to make but i like it

  57. CobaltKnight says:

    I like the fact that all of them are Daedric quests except laid to rest :)
    Also, since this was written before Dragonborn came out, none of those quests are there but i really like most of them, they’re really cool and often completely unique!

  58. I’m going to do the last one its sounds like the Hangover haha
    I’m lvl 54 i dont know it is going to hard?
    Check My channel
    http://www.youtube.com/rizzaclark !!!!!!!!!!

  59. I’ve pretty much finished the game (defeated Alduin, ended the civil war) and I’m only on level 43. Are there any quests that are as exciting as defeating Alduin?

  60. A Night To Remember was awful! I hated it. Way too weird for me.

  61. audriuska12 says:

    A Night to Remember doesn’t always start in Whiterun. It seems to be in the first tavern you visit after reaching a certain level (not sure which). My first playthrough, as a mage, I found him in Winterhold.

  62. I’m a lvl 50ish player any good challenging quests?

  63. Laid to rest was a sad one.. but it was fun. I want to do the A night to remember but i can’t figure out how.

Speak Your Mind


Find us on Google+