Out of all the pieces of DLC on offer in Oblivion Remastered, The Shivering Isles is arguably one of the coolest and most expansive. Not only does it boast a whole new continent to explore, but it also features new flora and fauna, and its very own assortment of quests to discover. While some may be expecting all the DLC to unlock as soon as you step out of the prison sewers following the tutorial, that’s not really the case, likely to avoid overwhelming players. So, for those curious as to how to start The Shivering Isles DLC in Oblivion Remastered, here’s what you need to know.
How to Begin the Shivering Isles DLC in Oblivion Remastered
To help make things easier, we’re gonna break down the process into four easy-to-follow steps.
1.) Finish the Tutorial
After escaping from the prison sewers in the opening tutorial, you’ll be able to head straight to the entrance of The Shivering Isles DLC. That said, while it’s possible to do this, it’s not highly recommended as some of the foes you meet on the titular isle are pretty tough. In other words, it’s worth leveling up and gathering some decent equipment first before embarking on your adventure into The Shivering Isles.

2.) Head to the Strange Door Near Bravil
In the Niben Bay lake next to Bravil, there’s a small island that you can swim to. If you’re unsure where to go, simply head to the location highlighted on the map in the image below. Here, you’ll find a knight called Gaius Prentus who is stationed there and valiantly attempting to guard a Strange Door.

As you approach the glowing purple Strange Door, a quest will initiate called A Door in Niben Bay. According to Prentus, all those who enter the peculiar portal return in a mad and aggressive state. Most would likely be put off by his advice. But to us? That sounds like an adventure!

3.) Enter the Strange Door
Once you’re ready, head into the Strange Door, and you’ll be transported to a small room with a table and chair. Here, you’ll find a mysterious character called Haskill, Chamberlein of the Lord Sheogorath.

4.) Take a Seat and Speak to Haskill
Before you can start chatting to Haskill, you need to take a seat in the chair in front of him. Next, initiate conversation with Haskill and he’ll clue you into what to expect on your adventure in The Shivering Isles. Once you’ve exhausted all the dialogue options, and once he’s delivered some interesting lore about the Prince of Madness, you’re free to begin your journey in a quest dubbed Through the Fringe of Madness, which is the beginning of The Shivering Isles DLC.
And with that, we come to the conclusion of our guide on how to begin The Shivering Isles DLC in Oblivion Remastered. For more, here’s how to join the Fighter’s Guild and how to join the Mage’s Guild. And for everything else, you’re in the right place at The Nerd Stash.