Skyrim’s Saddest Side Quests


For a game about epic battles with dragons, while a civil war rages, Skyrim also has its fair share of sad and even heartbreaking quests. Although it is over 10 years old, Skyrim is still finding ways to reduce players to tears with its mix of emotional side quests and environmental storytelling. As no two playthroughs are ever the same, even longtime players might not have encountered all Skyrim has to offer.


Skyrim lets players become true heroes as they fight to save the world after Alduin’s attack on the Skyrim city of Helgen. Players can also become a master thief, an assassin, or even the Arch-Mage of the College of Winterhold. In fact, one of Skyrim‘s greatest strengths is its versatility, as there as quests available to suit any Dragonborn a player can dream up.

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Many Side Quests Add Depth To Skyrim’s NPCs

A Skyrim screenshot showing the exterior of Frostflow Lighthouse.

With so many quests available, it is no surprise that some tug on the heartstrings more than others. A thorough exploration of Skyrim will give insights into the lives of its citizens, and not all of them have a happy ending. Not every quest can be about fighting draugr or collecting Nirnroot, and some of Skyrim‘s most memorable quests are also its saddest.

The Horror At Skyrim’s Frostflow Lighthouse

A Skyrim screenshot showing the interior of Frostflow Lighthouse, where the floor is covered in blood, and a table is broken in half with its contents strewn across the floor.

Frostflow Lighthouse is a lighthouse located a short way east of Dawnstar, and it is infamous among players for being one of the more tragic hidden Skyrim quests that is often missed. Upon entering, players will find a grisly scene, and the quest Frostflow Abyss” will automatically start. It seems a Redguard family had moved to the lighthouse from Hammerfell, but now none are left alive.

Using the environment and diaries scattered around the lighthouse, the Dragonborn must find out what befell the family of four. The answer is a rather obvious one as immediately players will hear the telltale chittering of a chaurus and find one in the main room of the lighthouse. However, this quest is sure to hit even the most hardened adventurer as it becomes obvious that this family came here in search of a new life and met a horrible end.

Vampires Aren’t What Make This Skyrim Quest Upsetting

A Skyrim screenshot where the player is looking at a Child's Coffin.

Traveling to Skyrim’s most mysterious city of Morthal, players will notice a burned out house next to the inn, and when asked about it, the innkeeper directs them to talk to Jarl Idgrod Ravencrone. It seems the house is the subject of quite a bit of gossip in town as the owner, Hroggar, escaped while his wife and daughter died in the blaze. However, the next day he moved in with a new lady, Alva, making the townsfolk believe he murdered his family, and the Jarl asks the player to find proof.

This begins the quest “Laid to Rest,” which involves investigating the house, checking on Alva, and eventually fighting a nest full of vampires, a great place to go if the Skyrim player wants to become a vampire. However, what really makes Laid to Rest” one of the saddest Skyrim quests is Helgi, Hroggar’s daughter. Her ghost can be spoken to throughout the quest, and she’ll help the player piece together what happened. It’s just so sad to hear a little girl talk about how she died, and at the end of the quest, she will thank the player before saying she is ready to sleep now.

Related: Skyrim’s Vampirism & When To Cure It

Surprising Sadness From Skyrim’s Creation Club Content

A Skyrim player looking down at the skeleton of a child, laying next to a wooden toy sword.

The Unquiet Dead is available with the Creation Club farming content, and there are two ways to start the quest. Players can either find the Goldenhills Plantation on their own, which is located just outside Rorikstead, where Skyrim‘s disturbing link to Oblivion is, or keep asking innkeepers for work until they receive the bounty for Restless Spirits. Either way, upon arriving at the farm, the Dragonborn will immediately be attacked by a ghost.

Investigating the house will reveal the journals of both adults living at the farm, Urval and his wife, Jonquil. When their son, Rin, goes missing, both suspect the other and make plans to kill their spouse. Jonquil poisons Urval, but he manages to kill her before succumbing to the poison.

However, the reality is much more tragic. Going into the child’s bedroom, his journal is under the bed, and in it, Rin talks about wanting to prove he was strong enough to fight in Skyrim’s civil war and join the Imperial Legion and how he would prove this by going to the old well to hunt a wolf. Sure enough, upon finding the well, players will see a child’s skeleton next to a toy sword. After placing Rin’s sword back in his room, the whole family will appear as ghosts and grant the Dragonborn the farm as thanks for helping them find peace.

Skyrim’s Narfi Will Tug On Heart Strings

A half-buried skeleton from Skyrim, with a plant growing through the ribcage and skull.

The tale of Narfi in Skryim is a really tragic one. Narfi is a beggar that lives near the remains of the home he shared with his sister, Reyda, on the edge of Ivarstead. It is clear when speaking to him that he is mentally ill, as Reyda has been missing for over a year, and Narfi will ask the player to look for her.

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This starts “The Straw that Broke,” a quest that many Skyrim players probably haven’t done. After speaking with the local innkeeper, the player will learn that Reyda used to leave town to collect ingredients on nearby islands. After searching the waters near Ivarstead, players can find Reyda’s body near the bridge just southeast of the town. Bringing her necklace back to Narfi will finish the quest but does little for his situation.

Players who join the Dark Brotherhood will meet Narfi again as he is the subject of a contract. Many fans have speculated on who would put a contract out on a beggar, with some theorizing that Narfi placed the contract himself as he couldn’t bear to live without his sister. If this is true, then Narfi is one of the most tragic characters in Skyrim.

A Broken Heart In Skyrim’s Winterhold

A corpse in Skyrim laying next to a boulder and an empty bottle.

There is a very surly drunk called Ranmir who frequents the inn in Skyrim‘s destroyed city of Winterhold, The Frozen Hearth. If players speak to the innkeeper Dagur, he will ask the Dragonborn to find Ranmir’s former lover Isabelle. Apparently, Ranmir used to be a very happy guy until Isabelle left, and Dagur hopes that finding her will fix the situation, and this begins the quest “Drowned Sorrows.”

Speaking with Dagur’s wife, Haren will reveal that Isabelle ran away with a theif named Vex. Vex can be found in the Ragged Flagon in Riften, where she says that Isabelle came to her looking for a way to make money. Vex sent her off to Hob’s Fall Cave and is surprised Isabelle did not reunite with Ranmir.

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Inside the hard-to-find Skyrim location of Hob’s Fall, players can find Isabelle’s body along with a letter to Ranmir. In the letter, she explains why she left, to make the couple some money for them to live happily together. Taking the letter to Ranmir will give him closure, and he will stop drinking.

The Cost Of Skyrim’s Civil War Hits Home

Angeline's Aromatics, a shop in Skyrim.

No News is Good News” is a short side quest that drives home the cost of Skyrim’s civil war in a way the main war questline fails to do. When chatting with Angeline of Angeline’s Aromatics in Solitude, she will ask if the player has been to Whiterun and met her daughter, who is stationed there. When the Dragonborn says they have not met her, Angeline will ask them to speak to Captain Aldis, an Imperial officer in Skyrim‘s civil war, on her behalf for news on her daughter.

Speaking with Captain Aldis will confirm Angeline’s worries. It turns out her daughter has been killed by Stormcloaks just outside of Whiterun. After telling Angeline the sad news, she will thank the player for letting her know.

Skyrim’s Bandit Problem Tears Family Apart

The remains of Leifnarr in Skyrim, laying in a cave next to a wooden wall covered in blood.

Heartwood Mill is west of Riften on the banks of Lake Honrich. The mill is owned by Leifnarr and Grosta who live there with their son Gralnach; however, when speaking with Grosta, it seems she is quite unhappy with her husband. She thinks he’s run away with another woman and wants the player to go find him and drag him back home.

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This starts the quest “Flight or Fight” and will take players to Broken Helm Hollow, a bad place to lose a Skyrim follower. The cave is filled with bandits, and after dealing with them, players will find a secret chamber containing Leifnarr’s body. This quest is so sad as Leifnarr has been missing for a few months, clearly being tortured for fun by these bandits while his wife thought he had left her.

The Saddest Quest In Skyrim Is Entirely Optional

A split image showing two Skyrim NPCs - Nilsine and Nova Shatter-Shield.

Joining the Dark Brotherhood was never going to result in sunshine and roses for the Dragonborn, but there is a contract that results in one of the most heartbreaking results in Skyrim. During the quest “Mourning Never Comes,” the player is asked to kill the former lover of a woman named Muiri. It seems he, in fact, used her to steal from Clan Shatter-Shield, and she wants him dead. However, Muiri has an optional extra task for players as she also wants them to kill Nilsine Shatter-Shield.

This is one of the Skyrim quests where the player’s the bad guy because this is when things get really tragic as Nilsine is the twin sister of Friga, who has already been killed by the Butcher on the loose in Windhelm. If players choose to kill Nilsine, it will be too much for the matron of Clan Shatter-Shield, Tova, to take, and she will commit suicide. This makes “Mourning Never Comes” easily the most heart-wrenching quest in all of Skyrim.

More: You Should Feel Bad For Completing These Skyrim Quests

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