Who doesn’t love a good thief playthrough? Sneaking around, stealing sweetrolls, trying to convince Brynjolf to have time for you. No? Just me? Well, no matter if you want to give your soul to Nocturnal, or try and find all those treasures Mercer left behind, there are plenty of mods for you.
One of my favorite playthroughs was as the long lost daughter of Gallus Desidenius. Iduna was born in Riften in 4E 176 to a Nord woman, who died birthing her. (Some SPOILERS ahead and throughout this post; also I don’t care how lore-friendly this RP was, it was fun!) The only thing she had to her name when she was brought to the Honorhall Orphanage was a silver necklace with the initials “With Love, GD” on the back. Luckily, a young woman named Constance Michel hid it from the horrible Grelod the Kind until my character was old enough to consider running away. Constance gave it to Iduna and apologized that she didn’t know who her parents had been. Iduna spent the next decade or so trying to survive in various other provinces. She finally returned to Skyrim so that she could explore the world of her parents (maybe even find out who they were) and learn more about where she came from. But mostly she wanted to help those that couldn’t protect themselves, like the orphans and poor and innocent. With a war on the horizon (and now rumors of dragons?), it was more important than ever that she learn as much as she could to help the people that needed it.
After returning to Riften and seeing how horrible things were for the children at the orphanage and how corrupt the political scene was, Iduna decided to join the Thieves Guild and attempt to bring about some change. Through various clues during her time with the guild, she realized that it was possible (and fairly likely) that Gallus was actually her father. She wanted to get revenge on Karliah until inevitably discovering the truth, at which point her ire was turned towards Mercer. Along her journey, she also discovered that she was the Dragonborn (of course) and killed Grelod the Kind (which started her on the path to becoming involved with the Dark Brotherhood). Throughout all her adventures, she tried to help those that needed it, but didn’t shy away from exacting a kind of vigilante justice. Eventually she married Balimund (using the Male NPC Overhaul version of him because…well he looks much better!), and adopted a whole bunch of children.
Here are some of the mods I used to really get into character and explore Skyrim as a thief with a heart of gold and daggers of steel. There are also some that deserve a mention for laying the groundwork for other great mods, some that I have not tried, but are in my current modlist, and others that I may try out someday (I wanted these to be in some sort of order, but alas, like the treasure room of my thief character, they are a bit of a jumbled mess):
While I love playing as a sneaky sneak thief assassin, I still like being a “good guy”. I know that’s oxymoronic, but what can I say? And the beauty of mods is that I can do it all! (cue evil laugh) This mod has gone through several iterations and quite a few upgrades to fix bugs, and is still being updated. I plan on trying out its latest iteration to see if the kinks have been worked out (of course, my previous “bugs” could have been mod conflict based, so take all that I say with a grain of salt). Some of the things this mod includes are ways to complete quests without being “one of the baddies”, stand up to Maven, and even get your soul back from Nocturnal.
“Never done an honest day’s work in your life for all that coin you’re carrying, eh lass?” If I had a coin for every time I heard Brynjolf say this, I would be able to buy all the cheese in Skyrim. This mod does all sorts of things, including preventing Brynjolf from approaching you unless you meet certain requirements (which can be configured via MCM). Other things that can be customized include number of radiant jobs required to display the trophies, requirements to delay other Thieves Guild quests, and more.
Another overhaul for radiant quests in the Thieves Guild, but this one also adds targets in ALL holds, among other QoL things like more radiant quests at a time.
Did you feel weird becoming the Guild Master instead of Brynjolf? Well, like nearly everything these days, there is a mod for that! And, just like many other mods on this list, this also reworks the radiant quest system (obviously not everyone enjoyed the rather tedious vanilla system).
Mercer may have been a terrible person, but he was a decent thief, and after he cleans out the vault, where does all that loot go? You will have to go on some quests through some (new!) dungeons, but you can recover “enough loot to make up for those 25 years of profit that Mercer stole”. This was the perfect “ending” for my playthrough.
Pretty much what it says on the tin; this mod allows you to “read” shadowmarks without literally memorizing them IRL.
I was pretty far into my first playthrough of vanilla Skyrim before I tracked down all of the Stones of Barenziah (totally cheated and looked up the locations). On my second playthrough, I decided to do that early on and was super rich and the game was totally unbalanced, and it was amazing. No regrets. However, there are definitely ways to improve on vanilla and here are a few mods that either visually overhaul the stones/crown, add some Quality of Life things, or, the most important of all, allow you to WEAR THE CROWN OF BARENZIAH AS THE GLORIOUS CONQUEROR YOU ARE!
I know that there are many that prefer other town and city overhauls, but JK’s is pretty much a mainstay in my modlists. I sometimes mix it up with adding other overhauls (and of course their patches), but I’m so used to JK’s at this point, that playing without feels weird. While not to everyone’s taste, both the general overhaul and the recent interior upgrades are just perfectly suited for me. So, to make Riften feel a little more cluttered and lived in, I use the below:
JK’s The Pawned Prawn (SE)
JK’s The Bee and Barb (SE)
JK’s Elgrims Elixirs (SE)
JK’s Mistveil Keep (SE)
A mainstay of my modlists these days, this mod combines a number of other mods together to create a cohesive overhaul of the docks outside of Riften. For a town that has a pretty big focus on fishing, there is little evidence of a solid fish trade (I mean where else do those boats go? We really need an overhaul of the waterways to add in a system of locks and canals to really keep our immersion, but I’m getting off topic…). With additions like a fish market and better and more docks and pathways, you no longer have to go through Riften (or swim) to get to the fishery. The latter is VERY important if playing with survival mods, as even The Rift gets pretty cold, especially at night, and you don’t want to have to swim unless necessary. This mod is out-of-the-box compatible with JK’s Skyrim and Dawn of Skyrim and has a number of compatibility patches for things like Carriage and Ferry Travel Overhaul, Lanterns of Skyrim II, and many more. Since it adds the following mods, this will even cut down on plugin space if you had planned on using any of these: Deck and Pier at Honeyside Riften, Riften Fish Market, Riften Docks Pathways and Better Docks. (Also, there are third party patches for other things on this list like Realistic Boat Bobbing, Jk’s Pawned Prawn, and Riften Extension – Southwoods District.)
This is a fairly newcomer to the modding world, but one that I am thoroughly enjoying. When used in combination with JK’s Skyrim or Dawn of Skyrim (or both) for the interior of Riften, and Riften Docks Overhaul for the exterior of Riften, this city truly feels like a hub. It is still a bit of WIP (only for the added quests, the location and NPCs all work as intended). The new NPCs have their own AI packages and are voiced acted. There is even a new quest with a dungeon (and another quest to come!) I love the new buildings and NPCs, and I especially adore the outdoor area in the middle where the residents spend their evenings around the fire. This new district feels a little like where the “salt of the earth (er Tamriel)” kind of people live rather than the seedier inner city.
I grew up on very large river with so many shipwrecks that divers would come from all over to explore, so it’s probably not a surprise that I really love exploring these same sorts of things in video games (I usually leave the survival mods off for these playthroughs though!). While there are a number of shipwrecks in the Sea of Ghosts, haven’t you wanted one in slightly warmer waters of Lake Honrich? Now, you can add one! I actually recently found this mod, so I haven’t used it yet, but it is in the modlist I am currently tinkering with.
There are a number of these mods, both modular and a most-in-one patched with JK’s Skyrim. There is even a patch for the Solitude one for Legacy of the Dragonborn. These are such fun mods that add just enough verticality to some of the big cities to really make a thief playthrough extra enjoyable. I definitely get a little bit of an Assassin’s Creed vibe from these.
Deadly Shadows for JK’s Skyrim (Solitude is separated out in the optional files, FYI)
DS Lairs – extra “lairs, hideouts, and homes”
There is nothing like climbing onto the roof of the house you just finished burgling to see the sun just starting to come up over the distant mountains and the fogs rolling over the Lake. To add some of these nice atmospheric moments, I use Morning Fogs (in conjunction with my weather mod of choice, usually Cathedral Weathers and Seasons).
Another mod I haven’t used, but would like to try someday (and it is regularly updated), this is an overhaul of Riften to “truly reflect its commercial history, and that of the guild, with treasure, traps, bolt holes, and walkways extending high above the city”. Not only has the city undergone a redesign, but there is new loot, a new player home, roof access to various places, and more.
This mod (that is only for LE, but I have heard is easily ported to SE) adds some verticality to Riften, making it “close, cramped, and navigable by rooftop”. I definitely get slight Novigrad vibes from Witcher 3 with this one, including the fact that you can’t enter every building. I may try porting it and adding it to my modlist because many of the comments look pretty favorable, including compatibility with some city overhauls.
This mod, created by EnaiSiaion, adds an illegal fighting arena for the dark side of Riften. The story has you climb the ranks against ten different foes and is voice acted. I have actually never used this mod before, but I have heard mostly great things about it. There are a few comments about bugs on the mod page, and it hasn’t been updated since October 2017. However, I do want to try it out one of these days and will add more here when I do!
This is another one that I found recently that intrigues me. I like the idea of a “thief with a heart of gold”, so something like fixing up the orphanage would fit perfectly into that character’s playthrough. I will definitely be trying this one out!
I really enjoy playing Elder Scrolls Online when I’m not playing Skyrim (and by “playing” I mean tinkering with my modlist…) and I spend a lot of time in Outlaws Refuges because of course I love a sneaky sneak character. After returning to Skyrim after I started playing ESO, I sorely missed the convenience of a fence in every city/town, so this is a perfect addition (depending on your modlist; there are some potential compatibility issues, but lots of patches).
Not specific to a thief playthrough, this mod rarely leaves my modlist, and nonetheless is a perfect addition to this list. Used as alternate entrances to cities, or another option to lay low, this adds an underground network to some cities and some forts. Be warned though, while you can use it as a means to avoid guards, there are other things in the underbelly of Skyrim that you will need to be prepared for.
Need to wash the grime and filth off after a long day of thieving? What better place to do so than at the local bathhouse? Found in the Canal District, this cozy location has an auto-undress feature, so it will be NSFW depending on your mods. There are added NPCs, including a vendor and some trainers. The NPCs even can be seen wandering around Riften, which is super immersive. This mod is compatible with Keep it Clean and JK’s Skyrim.
I have a bit of an obsession with all things honey and bees (stemming from my grandmother that helped raise me calling me her “Honey Girl”), so I was always drawn to Honeyside. While one of the best player homes in vanilla (in my opinion), except of course for the smaller size and the lack of storage. There are a number of mods that fix those issues, completely redesign the home, and more. Here are just a small sample of these:
This is one of my all-time favorite mod-added player homes and it fit in PERFECTLY with my playthrough because of the little added touches to show that it used to belong to Gallus. With a sliver of a perfect view of Lake Honrich and an entrance from the back “alley” of Riften, this small-ish apartment truly feels like that first apartment you got after leaving your parents’ home for the first time: heading to the big city, living frugally so that you can make ends meet, trying to find where you belong in the world. I might be getting a little sentimental about a video game apartment, but seriously, this one hits me right in the nostalgia.
The great Elianora has some amazing player home mods for Riften, but most of them are sadly only for LE (and I didn’t have much luck porting them, but maybe I’ll try again someday…). However, there is one that is probably one of my all-time favorites of hers: Ruska is a fairly small and perfectly cluttered home (a la the quintessential Elianora style). It is even compatible with Riften Docks Overhaul (as long as it is loaded before).
The other Elianora Riften player homes I love that are only on LE:
When I saw that the creator of a favorite player home mod of mine (Aureoy – Astronomer’s Loft – Small Loft Library Player Home in Whiterun – LE|SE) had created a new mod that added a home in Riften, I was sold immediately. Just like their other mods, this is the perfect size for someone starting out and it works for a variety of role-playing. It’s situated close to, but not conflicting with the Riften Garret, which is another bonus.
Also, worth mentioning, they also have a new player home mod adding an apartment in Windhelm: Emberbrand Cellar – Gray Quarter Basement Home (LE|SE) which gets even more bonus points for built-in compatibility with Capital Windhelm Expansion!
Technically a player home mod, but I like to use this one as an extension of the Thieves Guild in Skyrim. This mod adds a speakeasy beneath Whiterun that looks remarkably similar to the Ragged Flagon (…probably because it is essentially just the Ragged Flagon transplanted…). With trainers and crafting stations, and a backstory that states that “Gallus, the supreme thief among thieves in Skyrim and possibly the whole of Tamriel; he had one of the old portions of the Whiterun sewer system taken and rebuilt as his personal headquarters away from Riften”, this is a completely believable (in my opinion) addition to a thief-centric playthrough. It always seemed odd to me that there really was only a Thieves Guild presence in Riften (apart from the fences you can interact with later in the questline), so I enjoy adding this to my very overhauled Whiterun (with few conflicts).
An alternative to some of the other player homes on this list, this “safe haven” can be found in the Canal District. Not much more to say, but it is a fun player home (I generally prefer player homes that are up higher, but in a seedy city like Riften, this definitely fits a thief playthrough).
“Backstreet’s back, Alright!”…sorry, I couldn’t resist. As you may have gathered from reading any of this site, including this very post, I love player home mods. I blame growing up playing things like Sim City and The Sims. So, I was a little surprised that I had never heard of this home mod until quite literally days ago. I am planning on adding it to my modlist-in-progress (MIP) because I can’t get enough small lore-friendly and role-playing-friendly homes.
A perfect way to stay in the city when you are laying low planning your next heist, or need an alternate entrance (or exit) to avoid the guards, this mod is perfect. Compatibility varies, so be aware of that, but all-in-all, I love this mod for my thief playthroughs (and there are modular or merged options, so that helps.).
My go-to armor in Vanilla was Thieves Guild and then Nightingale, so let’s upgrade those a bit, shall we? Here are just a small sampling of the mods you can use to go all out:
Obviously including a significant amount of stuff beyond the Sneak and Lockpicking skill trees, these mods are well-known, but still deserve a mention as they definitely played a role in my thief playthroughs:
While I mostly play solo when doing a thief playthrough, there are some amazing followers out there that are particularly perfect for a thief playthrough:
In vanilla Skyrim, even if you have maxed out your Pickpocket skill line, you are capped at a 90% chance, but this increases that cap to 99%. This happens dynamically as you gain levels in the Pickpocket skill line.
I have not used this mod yet, but I REALLY want to. I know that it adds some pretty OP stuff, but the black market and heists sound really cool and it adds a bunch of spells called Shadow Magic based on the Nightblade class in ESO (which is by far my favorite class). I think I will try it out in the future, but will attempt to wait until end-game so that I don’t feel like it unbalances things too much (plus there are tons of mods to increase difficulty if needed). I will report back if and when I try this one out.
This is admittedly a little outdated, and I probably would recommend something like the DS options below, but I still want to mention it as I did use this quite a bit in the past. Shenk Thievery Overhaul not only adds ways to traverse cities more inconspicuously, but adds vaults in the some of the bigger cities, guards for more stores and homes, added tools and more loot for the discerning thief, and rival thieves. While there were even bigger plans for the mod, development seems to have stopped, but it was at least ported to SE. I no longer use this mod, instead opting for other replacers like Deadly Shadows and Sneak Tools, but thought it still deserved a mention.
Another overhaul carrying over from LE days, this adds player homes, equipment, new loot to steal, and changes to places like the Grey Quarter and Canal District so they are “slummier”. I actually have never used either the original or SE version of this mod, but like some of the others on this list, I would be remiss if I didn’t mention them, as they provided a lot of inspiration for other mods I do use and love. I am sure there are many out there that did and do love this mod, as it has quite a lot of downloads and endorsements.
Please remember to endorse any mods you download and like, and if you appreciate all the hard work that goes into creating a mod, consider giving kudos to the author on Nexus as well (the Give Kudos button can be found on the user’s page).
“…but the true joy of exploration is in the discovery, and so I leave the rest to you…”
~An Explorer’s Guide to Skyrim