Skyrim is by no means one of my favorite games; it feels like it's broken most of the time, the quests tend to get repetitive by the end of your adventure, and the game is really overrated especially when you look at those "best games of all time" lists. All that being said... I love the game, and I'd be lying to you if I didn't say the game didn't play a significant role for me as a gamer.
Whether you hate it or love it, Skyrim was massive when it released, and it's still pretty massive now (as Bethesda plans to rehash the game and shove it once again back down our throats). I don't know if I would call the game as innovative as games like Fallout 3 and Morrowind, but Skyrim took all the best elements from those games and gave us the biggest and most ambitious game Bethesda had ever released to this date.
And they did all this while nurturing an atmosphere that didn't take itself too seriously, and offered a good amount of fun. I'm talking about the constantly meme-speaking guards, Bethesda's continued support for mods, and the strange yet rare quests that were littered throughout the entire world.
These quests may or may not ask you to gulp a human being, or they may require you follow a demon's pet dog, and we're really only scratching the surface here. Truth be told, there were some strange moments in Skyrim, and today we're going to be looking at the strangest; 25 to be exact, and hopefully, we won't get you too weirded out to revisit the game and try a few of these out.
25 Rise In The East
The seas are usually untouched during Skyrim’s main quests, but surprisingly enough, some of the best side quests can be found there. Enter “Rise in the East,” a quest that sees you help the East Empire Trading Company.
Head out to the Windhelm Docks where you'll be asked to assist the East Empire Company with their pirate problem.
This quest makes it seem as if you’re traveling out of Skyrim to an uncharted land where you’ll have to take on a group of bandits known as the Blood Horkers. Once you defeat them, say hello to some sweet rewards.
24 Kyne’s Sacred Trials
While the first quest on this list taps into the inner adventurer in you, this quest is the first to offer a great deal of weirdness. You’re given the quest by Froki, who aptly lives in Froki’s Shack, which is kind of weird. I mean, should I just name my place Isaiah’s apartment?
Before I get off-track, Froki asks you to prove that you're a true warrior by defeating the guardian spirits of some of Skyrim’s toughest creatures. And the coolest part is that all the creatures look like ghosts and are pretty tough.
23 The Book Of Love
That’s right, all you lovebirds and romanciers out there, Skyrim’s even got you covered when you want to get in touch with your emotional side. Talk to Dinya at the Temple of Mara to start this one and she’ll ask you to help arrange some couples in Skyrim.
You’ll have to do your best love doctor impression and play cupid for the couples of Skyrim.
The quest even leads you to a ghostly couple that you have to help be at peace from beyond the grave. Pretty cool, and definitely weird if you ask me.
22 The Man Who Cried Wolf
Skyrim has a knack for quests that escalate rather quickly and this is a prime example right here. Talk to Falk Firebeard (cool name), who also happens to be Steward to the Jarl in Solitude.
Falk seems to think that something weird is going on in Wolfskull cave, and after you investigate you’ll see how right he is.
This quest gets freaky; you’re gonna take on some draugars and overhear some sacrifices and possible demon-related rituals. Remember, kids, don’t slay ritual leaders, unless it’s in Skyrim.
21 A Night To Remember
These are the quests that don’t get enough attention in Skyrim. You’re gonna want to talk to a man in a black robe named Sam who happens to be located in every major tavern.
After talking to Sam, he will challenge you to a contest, and from there, your wild adventure begins.
You’ll wake up in a temple and have to retrace your steps while also helping out all the people you angered during the night. Oh, and did we mention in the end you find out… you know what, we won’t spoil it for you.
20 The Mind Of Madness
Another prime quest to add to Skyrim’s weird roster; speak to Dervenin in Solitude, a man who can be found walking around the city. He wants his master to return from vacation from the Blue Palace, and if that sounds a bit cryptic, it only gets weirder from here.
When you go to track down his master you’ll end up being transported to his mind, where things get pretty trippy.
The quest draws inspiration from Alice in Wonderland and the only way to escape the mad man’s mind is to defeat all his negative emotions.
19 Unfathomable Depths
For this one you’re going to be taking on a few annoyingly tough enemies, so don’t say we didn’t warn you. Talk to an Argonian who can be found hanging around the docks of Riften.
You’ll be given the Lexicon, a strange cube, and you’ll be tasked with taking it into a deep dark crypt.
The place is swarming with rare enemies, but after you return the cube you’ll be given a power known as Ancient Knowledge which increases your blacksmithing by 15%.
18 With Friends Like These
The Dark Brotherhood is a group of goonies that have been around in every Elder Scrolls game, and they usually provide some of the strangest quests out there. Usually, they’ll task you with ending a high profiled target, but they also love to give you quests that sometimes feel too weird even for Skyrim.
This particular quest will be forced upon you once you start the Dark Brotherhood’s initiation, and upon falling asleep you’ll find yourself waking up in an abandoned shack being greeted by two guys; welcome to the Dark Brotherhood, I guess.
17 The Taste Of The End
Quests that involve moral judgment are usually left to games like Fallout or any Telltale game, but this quest offers a pretty fun moral dilemma: to eat or not to eat?
It’s an easy answer for any of us in the real world (well, at least I hope it is).
But here you’ll be given the same choice, and if you do choose to dine on some of this, then you’ll be given some really good rewards for doing so. Personally, I said screw it, and trust me it was worth it.
16 A Daedra's Best Friend
While walking around the outskirts of Falkreath, you’ll find a random stray dog who also happens to talk. You’ll find out that the dog is a companion to the Daedra Barbas, and now the talking demon pup wants to go back to his master.
When you return him, though, you’ll find his master is a lot less sentimental and will give you an option to end his canine friend who he’s grown tired of, or spare him and receive a lesser reward.
15 Forbidden Legend
Aaaand we're back to the Dark Brotherhood. I know, I didn’t expect to see them back here this early either, but here we are. Well, this quest doesn’t revolve around them, but it’s started by reading the Lost Legends book in their sanctuary.
This quest is probably one of the longest on this list, and also one of the most difficult in terms of combat and puzzles, so we recommend looking at a walkthrough. You’ll go through every crazy enemy in the game but it’s worth it for the one-of-a-kind reward.
14 Blood On The Ice
For this one, travel to Windhelm and visit the graveyard where you’ll be stopped by a guard that is on the lookout for a serial slayer. After some talking with the guard, you’ll head over to a new crime scene where you’ll be tasked to find the culprit.
Hope you brought your best pipe and Sherlock Holmes hat, because you’ll be sorting through evidence to catch your guy.
The plot continues to thicken as there’s a few twists and turns built into this one, so be prepared for a crazy ride.
13 Whispers In The Dark
Now here’s a quest that is true to the Dark Brotherhood and maybe one of the freakiest quests on this list. The Dark Brotherhood is falling apart as someone in the group has been showcasing traitorous behavior.
Astrid, the current leader of the group, thinks it’s Cicero, who acts as the jester but is also one of the most dedicated to their cause. One thing leads to another and then you’re locked in a coffin with the Night Mother. It’s so ominous being in that darkened coffin, and it only gets weirder when she begins to talk to you.
12 The Break Of Dawn
This is always a must-complete quest for me whenever I return to Skyrim, as it’s just too much fun. You’ll start this one out by visiting the statue of Meridia, and it’s near the mountainside of Solitude.
Meridia hates all things undead, as she’s the Daedric princess of life and energy. She’ll order you to take care of some wrongdoers at the bottom of her temple and afterward, she’ll give you a unique weapon called the Dawnbreaker. However, the part I love is when she propels you into the air to demonstrate the power she has over you.
11 Frostflow Lighthouse
This one is less a quest and more so just a really interesting place that you can visit that also happens to have a story take place within it.
Frostflow Lighthouse is located in Northern Skyrim, just south of Dawnstar and the place holds a pretty cynical story inside. Within the lighthouse is a slain family in the cellar and if you’re feeling sleuthy enough then it’s up to you to find out what happened to them... and let’s just say that there’s a lot more going on in that lighthouse then you’d think.
10 The Staff Of Magnus
I kind of always hated the College of Winterhold; it always just seemed like so much wasted potential for a place that could’ve been breathtaking. But I suppose I should save that rant for another day and instead we’ll talk about the best quest to come out of the college, “The Staff of Magnus.”
Through your time at the college, you’re going to be thrown into a field trip where you’re going to make a groundbreaking discovery. This discovery is going to lead to a lot of stuff going down, and that’s all we'll really say.
9 Dremora Encounter (Gaining Access To The Atronach Forge)
Once again, this is not an actual “quest” but is an adventure that is just so much fun we had to include it. For this one, you’re going to want to go to the College of Winterhold and talk to Phinis Gestor.
Unfortunately, your conjuration ability has to be at level 90 or higher to even attempt any of this.
But if you meet the requirements he’ll ask you to summon an unbound Dremora and fight it until it submits to you. Once you go through all the steps you’ll gain access to the Atronach Forge.
8 A Haunted House
Through this list, I’ve learned that Daedric related quests are probably the best in the game, and this one is yet another great example; this one concerns Molag Bal.
You’ll discover this quest by accepting to investigate an abandoned house that is located Markarth, and once making it to the basement you’ll find his mace. Bal will order you to find a priest that desecrated the mace and bring him to the location, and upon doing so he’ll possess the priest and force you to fight him with the mace. Truly a weird one.
7 The Blessings Of Nature
Here’s one that I didn’t even know existed prior to this list; head to the temple of Kyrnareth and talk to a priestess there that goes by the name Danica Pure-Spring.
She’ll tell you that she needs a weapon strong enough to extract the sap from the tree located in the middle of Whiterun. The weapon she’s after resides in Orphan Rock, but is defended by a rather rowdy race of folks. So be prepared to end tree people and other psychos just for some sap, hope it sounds like fun.
6 Civil War (Choosing A Side)
This one is weird in the sense that most players end up avoiding this quest even though it’s around at the very start of the game. That, of course, is choosing a side in the civil war and bringing an end to the conflict in Skyrim.
I actually have to commend the game developers for making this a central issue, but not requiring you to pick a side to end the game. What makes the decision hard is that both sides offer valid reasons for going to war, and picking one side seals the fate for the leader of the opposite side.
5 Delayed Burial
Well, we just couldn’t end this list off without having one more quest related to the Dark Brotherhood. This one involves two of the strangest members of our favorite bunch, Cicero and the Night Mother herself.
Cicero will be transporting the Night Mother, only for his cart to break down as you arrive. The great thing about this quest is that there are just so many ways to approach it. With Cicero being the main suspect in the group, many members will help you sabotage him right then and there, or you could choose to help the poor jester.
4 The Pale Lady
For this one, you’re going to have to discover Frostmere Crypt and find a female bandit located outside. Upon finding her, you’ll see that the rest of her bandit buddies, or former buddies, are attacking her.
Whether you save her or not, you can then talk to her and receive the quest or retrieve a journal off of her. Either way, you then can go into the crypt and come face to face with the spirit that is tormenting the bandits in the area.
3 J'zargo's Experiment
Ah, J’zargo, one of the strangest yet funniest NPCs throughout Skyrim. He’s located in the College of Winterhold. J’zargo speaks of himself in the third person and asks you to test out a brand new scroll he’s been working on.
After you use them, you can return for a reward. The reward is meager, but I just love doing anything involving J’zargo, and if you complete this quest you’ll have him as a follower. Trust me, hear the man speak and you’ll know what I mean.
2 In My Time Of Need
Another quest that offers a very tough moral dilemma, and a conclusion that will make you feel uncertain either way. A group of Alik'r warriors will eventually confront you in Whiterun asking if you can help them find a woman.
You’ll find her in the local tavern, but that’s where things start to get a little morally grey. You’re given a choice to either side with her and her story, or listen to the warriors who say that she’s a liar and has to take ownership for her crimes. This one is always fun yet heartwrenching to see play out.
1 The Wolf Queen Awakened
Although we mentioned this quest earlier, that was only the start of it; the end of the quest is much more satisfying as you get to fight one of the better bosses in the game. After completing “The Man Who Cried Wolf,” a courier will deliver a note to you stating that Falk Firebeard needs to talk to you about the ritual you disrupted.
Once you talk to him he’ll send you to another crypt where you’ll have to take on a slew of draugars, only to then be greeted by the Wolf Queen herself.