Complete guide to Elder Scrolls Oblivion Remastered side quests with expert strategies and progression tips
Introduction to Oblivion Remastered Side Content

The long-awaited Elder Scrolls Oblivion Remastered has arrived on PlayStation 5, Xbox Series X/S, and PC platforms, bringing enhanced visuals to the classic 2006 RPG experience. While the graphical upgrades are significant, the core content remains faithful to the original release, including all main story arcs and extensive side missions that made the game legendary.
Cyrodiil’s vast landscape is segmented into distinct territorial zones, each hosting numerous optional adventures. To simplify navigation through this expansive content, we’ve systematically categorized side missions according to their geographical origins and faction affiliations. This organizational approach helps players efficiently locate and complete quests based on their current location and character specialization.
City-Based Side Quests by Region
Major urban centers throughout Cyrodiil serve as hubs for numerous engaging side missions that reveal the political and social dynamics of each location:
- The Ghost Ship of Anvil – Investigate spectral maritime phenomena along the Gold Coast
- The Siren’s Deception – Navigate treacherous coastal encounters near Anvil’s shoreline
- Where Spirits Have Lease – Resolve supernatural disturbances in haunted residences
- Buying property in Bravil, Bruma, Cheydinhal, Chorrol, Imperial City, Leyawiin, and Skingrad – Secure housing investments across all major settlements
- Through a Nightmare, Darkly – Venture into dreamscape adventures with psychological challenges
- A Brotherhood Betrayed – Uncover conspiracy within organizational structures
- Two Sides of the Coin – Navigate moral dilemmas with consequential decision-making
- Corruption and Conscience – Expose institutional malfeasance in governmental systems
- A Shadow over Hackdirt – Investigate mysterious rural community activities
- Nothing You Can Possess – Pursue unique artifact collection missions
- Secrets of the Ayleids – Explore ancient Elven ruins and uncover lost knowledge
- Order of the Virtuous Blood – Join vampire hunting operations with specialized techniques
- Unfriendly Competition – Engage in commercial rivalry with strategic business tactics
- The Battle for Castle Kvatch – Participate in large-scale military engagements
- Knights of the White Stallion – Complete chivalric orders with honor-based questlines
Pro Tip: Prioritize property acquisition early as owned homes provide secure storage and convenient fast travel points. The Imperial City house offers the most central location but requires significant investment.
Settlement & Inn Adventures
Settlements and Inns:
- A Venerable Vintage (Weye) – Assist with wine-related complications and vineyard management
- Bear Season (Shardrock) – Handle dangerous wildlife threats in mountainous regions
- Goblin Trouble (Crestbridge Camp) – Clear hostile creature infestations from strategic locations
- The Gravefinder’s Repose (Roxey Inn) – Investigate burial site mysteries and ancestral secrets
- No Stone Unturned (Imperial Bridge Inn) – Complete comprehensive exploration challenges
- The Potato Snatcher (Faregyl Inn) – Resolve agricultural disputes with investigative work
- Revenge Served Cold (Harm’s Folly) – Execute calculated retaliation missions with stealth elements
- The Sunken One (Shetcombe Farm) – Recover submerged artifacts using aquatic exploration skills
- When the Vow Breaks (Whitmond Farm) – Address broken oath consequences through diplomatic solutions
- Zero Visibility (Aleswell) – Lift magical obscurement affecting entire communities
Common Mistake: Many players overlook these rural quests despite their often substantial rewards. Settlement missions typically offer unique items and substantial gold that scale well with character level.
Faction Questlines Deep Dive
Cyrodiil’s prominent guilds offer extensive multi-stage questlines that provide specialized advancement opportunities:
Fighters Guild Progression:
- Origin of the Gray Prince – Uncover orcish champion background stories
- Hand to Hand Training – Master unarmed combat techniques through practical applications
- Joining the Fighters Guild – Complete initiation rites for martial organization membership
- The Unfortunate Shopkeeper – Provide protection services for merchant establishments
- More Unfinished Business – Continue contractual obligation fulfillment
- The Wandering Scholar – Escort academic personnel through dangerous territories
- Trolls of Forsaken Mine – Eliminate monstrous threats from mining operations
- The Stone of St. Alessia – Recover significant religious artifacts
- Mystery at Harlun’s Watch – Investigate fortress disappearances with detective work
- Information Gathering – Collect intelligence through reconnaissance missions
- Expelled from the Fighters Guild – Navigate organizational discipline scenarios
Mages Guild Advancement:
- Joining the Mages Guild – Undergo arcane initiation procedures
- Bravil, Cheydinhal, Leyawiin, and Skingrad Recommendations – Secure endorsements from regional chapters
- Fingers of the Mountain Parts I & II – Master advanced spellcasting techniques
- Liberation or Apprehension? – Make ethical choices regarding magical creatures
- Information at a Price – Acquire knowledge through negotiation or coercion
- The Necromancer’s Amulet – Handle dangerous artifact recovery operations
- Mages Guild Suspension – Address temporary expulsion circumstances
Thieves Guild Operations:
- Finding the Thieves Guild – Locate clandestine organization headquarters
- May the Best Thief Win – Demonstrate superior larceny skills through competition
- Boots of Springheel Jak – Acquire legendary mobility-enhancing footwear
- Cast out of the Thieves Guild – Regain standing after disciplinary action
Dark Brotherhood Storyline:
- A Knife in the Dark (Welcome to the Family) – Execute initiation assassination contracts
- A Watery Grave (Blood of the Damned) – Perform aquatic elimination missions
- Accidents Happen (No Rest for the Wicked) – Stage covert fatal incidents
- Scheduled for Execution (To Serve Sithis) – Complete high-profile target removals
- The Assassinated Man (My Brother’s Keeper) – Investigate friendly fire incidents
- The Lonely Wanderer (Enter the Eliminator) – Track and eliminate mobile targets
- Bad Medicine (The Night Mother’s Child) – Utilize poison and alchemical methods
- Whodunit? (The Assassin’s Gambit) – Navigate social deduction scenarios
- Permanent Retirement (Of Secret And Shadow) – Conduct retirement elimination operations
- The Renegade Shadowscale – Hunt rogue Argonian assassins
Optimization Tip: Complete Mages Guild recommendation quests early to access the Arcane University, which provides essential enchanting and spellmaking services unavailable elsewhere.
Shivering Isles Expansion Content
The expansion content introduces Sheogorath’s realm of madness with uniquely bizarre questlines that operate under different logical rules:
- Through the Fringe of Madness – Initial transition into the chaotic realm mechanics
- Understanding Madness: The Lady of Paranoia – Navigate distrust-based narrative arcs
- The Cold Flame of Agnon – Manipulate unconventional elemental forces
- Ritual of Accession: Ritual of Mania or Ritual of Dementia – Choose alignment with philosophical polarities
- Rebuilding the Gatekeeper – Restore guardian entities through reconstruction missions
- The Prince of Madness – Engage with deity-level chaotic beings
- The Antipodean Hammer – Acquire reality-altering artifacts (listed twice in original)
- The Museum of Oddities – Curate collection of bizarre historical items
- The Fork of Horripilation – Obtain unique culinary implements with magical properties
- Everything In Its Place – Organize chaotic environments according to esoteric principles
- Taxonomy of Obsession – Classify and manage fixation-based phenomena
Advanced Strategy: The Mania/Dementia choice significantly impacts available quests and rewards. Mania favors creative, explosive solutions while Dementia rewards methodical, cruel approaches—select based on your character’s established personality.
Advanced Quest Completion Strategies
Maximize your efficiency and rewards with these professional gaming techniques:
Quest Sequencing Optimization: Complete city-based missions before venturing into rural areas, as urban quests often provide essential equipment and funds for wilderness exploration. Faction questlines should be prioritized based on your character build—warriors benefit most from Fighters Guild, mages from Mages Guild, etc.
Reward Maximization Techniques: Many quests offer multiple resolution paths with different rewards. Save before critical decisions to explore alternatives. Property ownership quests provide long-term benefits through storage and merchant access.
Avoiding Common Pitfalls: Don’t attack essential NPCs even when provoked—many quests become incompletable if key characters die. Maintain multiple save files before major decisions or difficult combat encounters.
Level-Scaling Considerations: Oblivion’s dynamic difficulty means some quests become harder as you level up. Consider completing mission-heavy areas before advancing too far in the main storyline to maintain manageable challenge levels.
Also Read: Is there a physical edition for Elder Scrolls Oblivion Remastered?
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