That’s where you first meet the delightfully mad Daedric Prince who looks like he stepped right out of Alice in Wonderland — Sheogorath.

Long-time veterans of Oblivion (and The Elder Scrolls series in general) met him long before that. But if you’re just now diving into The Elder Scrolls IV thanks to Oblivion Remastered, you’re about to cross paths with him again. And trust us — the quests tied to him are absolutely worth playing. So, how do you start the Shivering Isles DLC? This guide will walk you through it.

What Is Shivering Isles?

Shivering Isles is a DLC released back in 2007 for the original Oblivion. At the time, it was a separate purchase, but with the release of The Elder Scrolls IV: Oblivion Remastered in 2025, all previously released DLCs and add-ons are now featured in the base game — including this iconic expansion.

This massive DLC adds about 30 hours of new content, complete with a brand-new map, unique loot, and of course, new skills and abilities to master.

Image credit: Bethesda Softworks

In Shivering Isles, you’ll travel to… well, the Shivering Isles — also known as the Realm of Madness or The Madhouse. It’s one of the Planes of Oblivion, the alternate realms ruled by Daedric Princes. This one is home to none other than Sheogorath himself, who tasks your character with stopping a mysterious force threatening his twisted realm.

How to Start the Shivering Isles Questline

There are two ways to begin. The first is simply by exploring. If you’re the type of player who checks out every corner of the map, investigates anything suspicious, and always goes where something weird is happening — you’ll eventually stumble upon the Strange Door in Niben Bay near the town of Bravil.

But if you’re here for a step-by-step guide to make sure you don’t miss anything, here’s how to kick things off:

  1. Travel to the city of Bravil
  2. Talk to the townsfolk — ask about rumours and what’s been going on nearby
  3. Eventually, you’ll hear chatter about Strange Doors appearing in the area
  4. Head to the location mentioned in the dialogue
  5. Speak to the guards stationed near the door
  6. Defeat the deranged Dark Elf who bursts out of the portal
  7. Listen to the voice of a Daedric Prince looking for a new champion — then step through the Strange Door

Image credit: Bethesda Softworks

When’s the Best Time to Start These Quests?

The difficulty level of this DLC is balanced quite well (even in the original version), so you can technically jump in at any point — whether you’re just starting out or already deep into the main story. However, for the best experience — especially when it comes to loot scaling and survivability — we recommend waiting until at least level 20. That way, you can handle the challenges and make the most out of the high-tier gear you’ll find along the way.

So — ready to embrace the madness? Grab your gear, keep your wits (somewhat) intact, and prepare to enter the realm of Sheogorath. It’s weird, it’s wild, and it’s one of the most unforgettable adventures in The Elder Scrolls!