There are lots of quests to encounter throughout Skyrim and its expansion packs. While some missions are relevant to certain factions and storylines, others are standalone side quests. Many of the missions you can play in Skyrim contain unique challenges that range from collecting alchemy ingredients to defeating a legendary warrior.

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If you're looking for a challenge, then the following quests are the perfect adventures to partake in. With that in mind, here are the hardest challenges waiting for you in the land of Skyrim.

Updated August 15, 2022 by Michael Caruso: Skyrim is full of interesting quests for you to encounter throughout the world. However, not every mission is difficult, and many are incredibly easy. Occasionally you'll encounter a quest that's hard to complete, and these are often the most enjoyable of the bunch. Some quests are difficult for reasons other than difficuty, such as tough choices involving morality. If you like questing, then you'll want to know about even more of the hardest Skyrim quests that you can sink hours upon hours into.

15 The Cure For MadnessSkyrim Cicero Standing In A Sanctuary

Cicero is a notable character in the Dark Brotherhood questline. Although he betrays the guild at the beginning of this mission, he's still a beloved character among the Elder Scrolls fanbase, which makes whether or not you side against him a difficult decision. You'll have the chance to kill Cicero at the end of the quest, but you can also set him free, and then he'll become a follower after completion of the Dark Brotherhood questline.

In addition to this difficult decision, "The Cure For Madness" is also challenging in that you have to explore an old Dark Brotherhood sanctuary, and defeat many ghostly enemies on your way to finding Cicero. Overall, this quest is one of the hardest quests in Skyrim's Dark Brotherhood questline.

14 The Way Of The VoiceSkyrim Character Climbing The 7,000 Steps

"The Way Of The Voice" is one of the most inconic quests in Skyrim, both because it's a main quest, but also because it requires you to climb a perilous path full of dangers — such as dangerous animals that are difficult to defeat when you're a low level. You'll usually start this quest at a lower level since it's one of the first main quests in Skyrim, so it's quite a challenge at first.

You'll also need to climb hundreds of steps to get to the top and meet the Greybeards, making it not only difficult but a long quest overall. To top it all off, the beginning of this upward path is in Ivarstead, which you can't get to via a regular carriage — meaning you'll need to walk there. Overall, this quest is difficult both because of the long walk, and the powerful enemies you encounter on the steps.

13 PaarthurnaxSkyrim Paarthurnax Sitting On A Word Wall

Paarthurnax is one of the most interesting characters in Skyrim. He has both an interesting backstory and he's very kind to the Dragonborn, putting his past aside to help save the world from Alduin. However, Delphine and The Blades will eventually approach the Dragonborn asking for them to kill Paarthurnax, which is optional.

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Killing Paarthurnax is a challenge since he's a powerful dragon, but it's also hard because he's changed a lot — and the Blades may be wrong in condemning him after he helped the Dragonborn and their allies. Overall, the choice is up to you, but both the decision and potential battle are very difficult.

12 Destruction Ritual SpellSkyrim Character Speaking To Faralda

The content in the "Destruction Ritual Spell" quest is difficult, but what makes it particularly challenging is that you have to reach level 90 in the Destruction skill to start it. Upon talking to Faralda at the College Of Winterhold, you can complete this quest to earn access to a powerful selection of Destruction skills.

You also have to travel to three different locations before the quest is complete, which means you'll have to do a lot of walking and fighting powerful enemies throughout your journey if you want to unlock the higher tier Destruction spells. The trip through multiple locations, combined with the grind required to reach Destruction level 100, makes this one of the toughest missions in Skyrim.

11 Hitting The Books

Skyrim Urag Speaking To The Dragonborn

The College Of Winterhold questline has quite a few lengthy quests, that take a lot of power and time to complete. One of the longest and most difficult missions you can complete for this faction is "Hitting The Books," which is one of the first main quests you get sent on by the college.

After speaking to Urag, he'll request that you collect lost books from Fellglow Keep. There are magical enemies guarding these books, so getting them is quite the challenge. In addition to the long dungeon with tons of enemies, you'll also have to fight a mage named The Caller, which is a tough boss fight that will test your strength against magical attacks.

10 At The Summit Of Apocrypha

Skyrim Miraak Casting A Spell

"At The Summit Of Apocrypha" is the final quest in the Dragonborn DLC's main storyline. During this quest, you have to travel through the Black Book: Waking Dreams and defeat Miraak. Since Miraak is essentially the final main boss in Skyrim, he's quite difficult to defeat.

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Not only will you have to face Miraak, but there are also dragons present during the fight, adding double the trouble to this mission. Miraak is particularly powerful since he can use shouts and has a unique equipment set that grants him many powerful bonuses.

9 The Wolf Queen Awakened

Skyrim Ghost Sitting On A Throne In A Dungeon

"The Wolf Queen Awakened" is a mission that you must complete to gain the respect of Solitude and Elisif The Fair. Although the quest has many trivial steps, the hardest part is by far the final fight. Before you face Potema, you'll need to defeat waves of Draugr. Unfortunately, this section of the fight is much too difficult for low-level adventurers, especially if you're playing on a high difficulty.

If that wasn't hard enough, you also face Potema herself as the final boss, which is difficult since she can use Destruction magic and summon Atronachs, so fighting many magical enemies is a core component of this battle. Once you defeat Potema, you'll feel an immediate sense of pride that you sent The Wolf Queen to her grave.

8 The Black Star

Skyrim Realm Inside The Black Star

"The Black Star" is Azura's Daedric Quest in Skyrim. Daedric Quests are known for being more difficult than standard side missions, but "The Black Star" takes this to an entirely different level because of the nature of the enemies you face.

After beginning "The Black Star" by traveling to the Shrine Of Azura, you need to recover Azura's Star, which is the easy part of the quest. Next, you have to enter the star and defeat Malyn Varen, which is easier said than done. Dremora minions are also a threat inside the star, which are difficult in their own right, especially on higher difficulty settings.

7 The Eye Of Magnus

Skyrim Ancano Next To The Eye Of Magnus

"The Eye Of Magnus" is the greatest trial you can complete for The College Of Winterhold. This is the mission where to finally go toe-to-toe with Ancano, the High Elf who has been causing trouble at the college. The final quest of each of Skyrim's main factions is difficult, but Ancano offers a special type of challenge because he paralyzes your allies and followers upon beginning the fight.

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Ancano can use many powerful spells, and he's invincible unless you use the Staff Of Magnus to close the nearby Eye Of Magnus. With Ancano's unfathomable power and your lack of companions, he's one of the strongest enemies in the base game. Upon putting an end to Ancano, you become the College Of Winterhold's Arch-Mage, which is quite a title to behold.

6 Lost To The Ages

Skyrim The Forgemaster Inside A Dwarven Ruin

"Lost To The Ages" is difficult for two primary reasons. The first is that this side quest takes a long time to complete. You have to track down Aetherium Shards, which are each in different locations, all while defeating powerful Dwarven foes. There's even a powerful boss named The Forgemaster that you'll face before claiming your Aetherial reward.

"Lost To The Ages" is a Dawnguard DLC quest that you can start by traveling to Arkngthamz. If you're up for a challenge and don't mind getting your boots wet in Dwarven Oil, then "Lost To The Ages" is the perfect side mission for you.

5 Elder Knowledge

Skyrim Glowing Mushrooms Inside Blackreach

"Elder Knowledge" is one of the longest main quests in Skyrim. The goal of this mission is to travel into Blackreach and retrieve the Elder Scroll - the ultimate task in an Elder Scrolls game. Along with the length of the dungeons you need to travel through to find the Elder Scroll, you'll also come face to face with hordes of challenging enemies, many of the Dwarven variety.

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There are also Falmer within the deepest reaches of Blackreach, which are one of the toughest enemy types in Skyrim. It's fitting that "Elder Knowledge" is one of the hardest quests in the main storyline since it involves an Elder Scroll, but it's worth it in the end when it helps you defeat Alduin.

4 A Return To Your Roots

Skyrim Crimson Nirnroot Inside A Building

"A Return To Your Roots" varies in difficulty depending on whether you take a combat or stealth approach. After reading Sinderion's Field Journal in Blackreach, you have to travel around the Dwarven Ruin and collect 30 Crimson Nirnroot. Crimson Nirnroot is similar to regular Nirnroot, but it's red instead of green.

Not only is the Crimson Nirnroot spread out over the large area of Blackreach, but there are also powerful enemies lurking in the shadows. It may take you a few hours to find all the Crimson Nirnroot in the ruin, but it's all worth it once you return it to Avrusa Sarethi at Sarethi Farm and gain Sinderion's Serendipity, which gives you a 25 percent chance of creating a second potion while crafting alchemical mixtures.

3 Under New Management

Skyrim The Dragonborn Becoming The Thieves Guild Leader

"Under New Management" is a lengthy quest because the only way to finish it is by playing through the entire Thieves Guild questline and completing 20 other radiant quests for the Thieves Guild. Technically, "Under New Management" is separate from the radiant quests, but they're a prerequisite for completing this mission.

The goal of "Under New Management" is to commit crimes throughout Skyrim, returning the Thieves Guild to glory. The requirements include completion of 20 Thieves Guild radiant quests, along with "Imitation Amnesty," "Summerset Shadows," "Silver Lining," and "The Dainty Sload." Stealing so many items is a mighty task, even for the legendary Dragonborn. Upon finishing your crime spree, you'll become the new leader of the Thieves Guild.

2 No Stone Unturned

Skyrim Stone Of Barenziah Sitting On A Table

Unlike many of the other quests on this list, "No Stone Unturned" isn't difficult because of its combat trials. You need to track down 24 Stones Of Barenziah throughout Skyrim and return them to Vex from the Thieves Guild. The locations of the stones range from dungeons to guild headquarters, so collecting them all requires a lot of patience.

However, the unique effect you earn for finding all 24 Stones Of Barenziah is worth the wait because the Prowler's Profit ability significantly increases your chances of finding gems in containers. If you desire to be the wealthiest adventurer in Skyrim, then you need to collect the Stones Of Barenziah ASAP.

1 The Ebony Warrior

The Ebony Warrior Speaking To The Dragonborn In Whiterun

"The Ebony Warrior" is Skyrim's final challenge, so it's fitting that it's difficult. After reaching level 80, you'll encounter The Ebony Warrior inside the main cities of Skyrim, where he'll challenge you to a battle. It's hard to resist the challenge when you know you'll have access to The Ebony Warrior's shiny equipment after defeating him.

The battle itself is truly challenging. Not only does The Ebony Warrior have a powerful set of ebony equipment, but he can also use shouts, similar to a Dragonborn. Additionally, The Ebony Warrior heals himself with Restoration spells, so he can take a lot of damage before you strike the final blow and collect his strong gear.

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