Shadows over Loathing quests
This page contains general information about quests. For some quests, a walkthrough is provided here. For others, see the section's main article for the location page with the details.
Enter the diner and reach the bathroom to reveal (and choose) what's underneath that magazine. (Or try standing in traffic to see the only Game Over screen possible in the entire game.)
- Ask Ethel, the lady at the counter, about the bus to Ocean City.
- Choose your character's motivation to gain an associated perk.
- See The Nightingale Diner for the full list of choices.
- Exit the diner to take the bus.
When the bus comes to a stop, the driver hands you an empty gas can. You need to fill it from at least 3 sources then return to the driver.
There aren't exactly side quests available here, but you can hit some story beats, gather some extra items, 3x the required gas for no reason, and up to 45 , plus 10 for leaving the area. There's also a very nice secret reward if you're thorough and observant.
Carry on to Ocean City. Once you arrive, check in at Murray's Antique Store. Jessica fills you in on the situation: your uncle Murray was researching cursed artifacts and has gone missing. You need to track down a series of artifacts to help find him. Meet Gabby, your first companion. You can also choose your character's personal pronouns in case Jessica's first guess missed the mark.
Before you can get some desperately-needed sleep, you need to pick up a cursed hat.
- Speak with Jessica, who gives you the key to the nearby shut-down newspaper office.
- You might check along the street to the left for an easily-missable character interaction.
- Go to the The Watchful Eye Office on Plunkett Street, to the right from the shop.
- Searching the employee desks grants you several items and informs you a trap door is hidden below the water cooler. Specifically, check the middle desk in the column to your left as you enter.
- Move the cooler aside and go through the trap door.
Two "moist fellas" block your way here. You have two options:
- Dive right in and fight them.
- Fiddle with the nearby control console for the pneumatic tube they're conveniently standing under. The pneumatic tube system operation manual from the desks above is helpful, but you'll need to interpolate missing information; remember ROYGBV.
- Solution: Push the green button, pull the lever, and turn the knob to C.
Get 5 , grab the terribly cursed fedora, and return to the antique store.
- Talk to Jessica.
- Go to Your Room, open your valuable luggage which you will definitely need, and sleep.
- Have A Dream About School in which you pick your character class and gathering minor.
Chapter 1: Welcome to Ocean City
Chapter 1 Main Quest
Wake up in the morning and Jessica gives you a to-do list and 100 . She asks you to track down a cursed watch of some kind in the speakeasy down the street. She gives you a password to unlock the speakeasy, Oliver's Place. You should also check the bookshelf for your first class skill book. The shop next to the antique store, Cola Wars Surplus, is now open.
- Go to the speakeasy and talk to Fancy Dan, the barkeeper.
At the Refrigerator Factory, you find some mob guys blocking your way. They demand 500 to pass. You can (eventually):
- Pay the 500 Meat as requested.
- Knock the price down to 300 with 3ish Moxie.
- Pay just 100 with 5ish Moxie.
- Pay zero by defeating them in a fight, though it's not possible to win without getting better skills and equipment.
- For now, just ask them how to find that kind of Meat.
They add Goldthwait Park to your map, where you can start taking on side quests.
- Explore the city to your heart's content. See Goldthwait Park and the other side quests below.
- Don't worry too much about saving Meat for the mob guys; you can always get more by wandering and/or just kick their butts instead.
Once you get past the mob guys, break in to the factory and witness a cutscene. Oliver Gluck is about to pick up hooch from the mob, but your nemesis teleports in. They trigger some kind of anomaly which transforms Gluck into a weird shadow monster. They then leave, after ordering the shadow monster to kill you.
- You can back away and use the nearby crane controls to drop a refrigerator on Shadow Oliver.
- If you fight instead, the two mob guys help you subdue the shadow monster.
- Return the deed to Fancy Dan to become owner of the Speakeasy.
- Then return to the antique store and speak with Jessica.
As you enter your room, your uncle's handyman, Charles Wallace, stops you to ask you to choose a new tenant for the street's vacant shops. You're given three options selected at random from nine possible shops. See Plunkett Street for the list.
- Sleep in your bed to have a A Fitful Dream.
Day 1 Ongoing Quests
Find booze for the speakeasy
Throughout the game, you can find additional booze and other ingredients for your speakeasy, giving you more and better options for your booze buff.
Today, just one new bar material is available:
Bring people to the Hobo Camp
After you show kindness to a few hobos, one will invite you to their camp during Ocean City wander events. Throughout the game, you can send hobos to the camp to aid the community. You gain 15 for each hobo you send to the camp. After you learn Hobo Literacy from Letters, each hobo you meet can also teach you some codes to increase your skill at translating hobo glyphs. Help enough hobos, and they can help you in return in the final chapter.
- The camp's initial residents include Fifty-Two, King Johnny, Letters, Veronica, Wade, and Washy.
- Howie is there if you helped him in the Prologue.
- Gus is there if you gave him Meat in the Prologue.
You can recruit additional hobos in Ocean City:
- Give Obie 10 or 50 at Goldthwait Park, then (with the groundskeeper's quest) ask him to leave as a favor.
- Samuel stands in front of Hiram's Grocery, misguidedly hoping for work. Give him 10 to get him on the road and into the camp.
- Give Dusty 5 at Ocean City Boardwalk and she'll find her way to the camp.
Hobos refuse to speak to people with Shadow taint level 3 or higher.
Ocean City Side Quests
There's no time limit on most side quests in the game; you can put 'em off all day (or even until later days) and still complete them. Don't forget to spend on new stuff and on new skills as you explore the city and complete quests.
You probably want to grab your class skill books too. Find them:
- On the bookshelf that just arrived at Murray's Antique Store
- At Cola Wars Surplus
- And the first aid kiosk at Ocean City Boardwalk.
Do contractor work at Goldthwait Park
Goldthwait Park is likely your first source of side quests. To mark it on your map, talk to the Mob guys in front of the Refrigerator Factory and hear their demand. Then ask them or Jessica about earning more Meat.
Total reward: 375 , 30 (plus any combat XP), and a random ring.
Find Charles' chuck key
Any time after getting the mapkin, return to the antique store and find Charles Wallace checking his pockets. Talk to him, offer to help, wander two or three times, and give him the chuck key you find.
Test some dubious grenades for Cola Wars Surplus
The fella at Cola Wars Surplus is happy to pay you to probably get yourself killed.
Get your fortune told for some reason
When you have 150 to spare, get your fortune at Ocean City Boardwalk three times.
Find the missing cremains for St. Polycarp's
Find St. Polycarp's Cathedral in Ocean City wander events..
Find some Snackle Cakes for Marvin
While wandering, you may spot a man sitting on a mailbox — Marvin's Mailbox. Bring him some snacks.
Solve the murder at Ms. Brewster's
Buy something from a wandering salesman to put Ms. Brewster's Home for Travelling Salesmen on your map.
Investigate Ernst Zimmer's incredibly haunted house
A wander event alerts you to some eerie music emanating from an Eerie House. Destroy the terrible and beautiful object that's threatening the place. Or don't.
Rewards: Zimmer's cello (a powerful melee weapon for such an early quest), 10 , and the continued safety of the world, at least for a little while.
Confront the local gangs
During wander events, you encounter several gangs and... other things... terrorizing Ocean City. Put a stop to them. These tasks aren't tracked as side quests in your to-do list. However, they do provide some valuable rewards, and cleaning up the town affects the game's ending.
These all require fighting to complete. Pacifist characters keep away.
- Rewards: Ciabatta's pants, some mana-enriched flour, ~75 , and the recipe for the dough baby familiar, plus 12-17 fight .
- Rewards: 200 , 12 fight , some toolbox items, and an upright glockenspiel as decoration for Your Room.
Tin Lizzies: After a couple of encounters with the girls, find The Tin Lizzies' Chop Shop.
- Possible rewards: various loot; 10-17 fight ; tin whistle; the Crescent Throne in Your Room; the Tin Lizzies leave you alone in the streets; and they may also give Meat and items instead of fighting you.
Tentacles: The first time you defeat some tentacles while wandering, you find your way to the truly awful Tentacle House.
- Cleaning out the house yields a fairly impressive collection of loot and around 37 (in a row) from all the fights and the toilet.
Chapter 2: The Spooky Forest
Chapter 2 Main Quest
When you emerge from your room, Jessica asks you to track down a cursed compass. She gives you a bus pass which lets you travel between locations, a Crystaldream Lake postcard, and unlocks the Crystaldream Lake Lighthouse location.
- Take the bus to Crystaldream Lake, go inside the lighthouse, and talk to the keeper.
The lighthouse is flooded, and the pump needs a Glaxton valve. Lighthouse keeper suggests checking Valley Hardware.
- Ask the man at Valley Hardware about Glaxton valves.
- Head into the back room and step through the time portal.
- Now in 1917, ask the hardware guy about Glaxton valves to unlock Crystaldream Dam.
Go back through the time portal and travel to the dam. Your nemesis interrupts you on the road. Fight them or drive them off with your powerful muscles / brain / coolness. (The stat test is fake; you can always pass it.)
- Pass through the time door at the dam and speak to the 1917 construction worker.
- Either defeat him in a very hard fight, or give him five different food items.
- Past him, get a Glaxton valve from the last crate.
Return to the lighthouse.
- Install the valve on the pump outside.
- Talk to the lighthouse keeper, follow him upstairs, and ask for the compass.
- He gives you a Geiger counter to help track down another old compass to trade for his.
Travel to The Old Junkyard.
- Go into the opening and pick up a shovel. Two ways to proceed:
- Defeat the fairies to the right and take the passage in that direction. Defeat another group of fairies and take the passage right-down.
- Take the passage up and find a small tunnel at the right side of the room. Crawl through with 5ish Moxie. Take the passage down.
- Find a spot on the right side of the room where the Geiger counter ticks furiously. Dig up an old compass with your shovel.
Return to the lighthouse and take the stairs up to its keeper.
- Trade the old compass for the keeper's cursed compass.
- Talk to Jessica back at the antique store.
- If you wish, uncurse the compass and transform The Compass' Curse.
- Head to your room. Charles Wallace has you choose another store.
- Sleep and have a Another Fitful Dream.
Day 2 Ongoing Quests
Day 2 booze
- Find a crate of vodka on a shelf at Grandpa Joe's Distillery.
- Find a crate of rum on the floor at Grandpa Joe's Distillery.
- Then buy Barnaby a drink for a clue hinting at Charles Wallace. Ask Charles about illegal booze and get a crate of gin.
Day 2 hobos
- Help Beanie at The Old Junkyard with 5 Muscle.
- Cut Doc loose from a coccoon at Beppo's Hole.
- Vandalize the sign at the Village of Sandwich gazebo in 1692, then find Creamy Steve there in 1928.
Work for the Mob
A Mob gentleman is in your room when you awake. You can agree to do contract work for the Mob, a questline that will span the rest of the game. The Mob can also help you in the final chapter.
Crystaldream Lake Side Quests
Save the Village of Sandwich
Witch trial? Oh, that trial.
Reward: Encyclopaedium of Bloode
Find Crystals for Crystal
Crystal needs crystals for her Crystal Store so it can be a crystal store.
Rewards: 20 , a twinkling crystal statuette, and access to Crystal's crystals.
Get Worms for Grady
Help Grady stock up his shop.
Chapter 3: Back to School
Chapter 3 Main Quest
Jessica asks you to track down a cursed textbook in S.I.T. Campus, Porkham. The library won't allow access if you're not a student, so you need to enroll. And only faculty and alumni are allowed in the stacks where the cursed book is, so you need to graduate.
- Choose three classes at S.I.T. (Admissions Office).
- Note: If you don't want to miss one of your class's combat skill books, pick
- a Botany major if you're a Pig Skinner.
- a Geology minor if you're a Cheese Wizard.
- You can pick a Spiders elective as a Jazz Agent, but due to a bug, you'll find Advanced Poison Chemistry instead of your class's skill book.
- Note: If you don't want to miss one of your class's combat skill books, pick
- In any order, complete your major, minor, and elective. See S.I.T. (Admissions Office).
- Find Librum Umbra Malum Ovilla. See S.I.T. (Library).
- Return to Murray's Antique Store and tell Jessica it's found.
- You may uncurse the book into 101 Delicious Mutton Recipes and/or lift The Book's Curse.
- Charles is out, but Jessica has you pick a third shop as you enter your room.
- Go to your room and sleep to have Yet Another Fitful Dream.
Day 3 Ongoing Quests
Day 3 booze
- Scalar Wing: Get a crate of cola from the cola machine.
- Rufus's Lab: Grab a container of absinthe after agreeing to help Rufus.
- Zeta Omega Omicron: Find a drum of vermouth in the basement.
- Underground Fishman Bar Goldthwait Park: Yoink a barrel of olives. Requires 7ish Moxie and the antique manhole opener from Rufus.
- Professor Kalos' Holiday Home (Crystaldream Lake): Grab an infinitely juicy tomato from the science shed. Requires Botany major.
- Meta-Acoustics Classroom: Take a barrel of tonic water. Requires Meta-Acoustics minor.
- Culinary Science Classroom: With 6ish Mysticality, make a dewar of simple syrup. Requires Culinary Science elective.
Day 3 hobos
- Meet a man with a bindle while wandering. Ask about his wares to unlock Ovid's Store. Show Ovid the Royal Summons from King Johnny to send him to the hobo camp.
- With Hobo Literacy 9, meet Walter under S.I.T. (River Bridge). You need the municipal contraption from Rufus to get down there.
- Give Calendula 87 upstairs at Zeta Omega Omicron.
- The sad-looking hobo selling pencils in front of Fission Chips can't actually be sent to the camp. However, you can learn hobo codes from him after bringing him an S.I.T. coffee mug from the gift shop.
Day 3 Mob jobs
Don T. has three tasks for you at S.I.T.
Help Rufus find his sibling
This questline spans the rest of the game, and Rufus can help you in the final chapter.
No reward for this today, other than the possibilities it opens.
S.I.T. Campus Side Quests
You need to sign up for classes before you can explore the campus.
Bring the janitor his dentures
- Visit S.I.T. (Spider Wing).
- Ask the janitor in S.I.T. (Main Lobby) about the Spider Wing and accept his request.
- With 5 Spooky Armor, check the drinking fountain at the Spider Wing and find the janitor's dentures.
- Return them to him in the Main Lobby and earn 30 .
You can also ask the janitor about the Vector Wing to uncover a hobo code there.
Find some barbecue sauce for Floyd
- Talk to Floyd Carbuncle, then fill his empty sauce cup at a fountain in S.I.T. (Barbecue Wing).
- Return to Floyd for 30 .
Get some wood chips for a cuein' frat guy
Check a notice board in S.I.T. (Spider Wing) to mark Zeta Omega Omicron on your map. The guy barbecuing indoors needs some mesquite chips.
Get a lost jacket for a chilly frat guy
If you help both frat guys on Day 3, they'll be at The Purple Door on Day 4. Talk to them then for another 35 .
Chapter 4: Swamped
Chapter 4 Main Quest
Charles Wallace has been kidnapped by gatormen. Are you a bad enough dude to rescue the handyman? You need to find a cursed key as well.
Travel to The Big Moist doing various side quests to find campsite remnants. Check the notice board at the bus stop to get a location or two on your map. Examine the campsites, which you find at the first three of these locations you visit:
- Abandoned Campsite. After talking to the frogs at The Frogbog, find it on the way to Haim Quarry.
- Feldman Quarry. Offer to help the pilot at A Plume of Smoke build a runway.
- Gatorman Hamlet. Find this as part of the Largemouth Bass & Sons quest.
- Gatorman Village. Accept the quest at The Leathers Brothers to find it.
- Moonshiners' Cave. At Moonshiners' Shack, examine the tire inside, then the tire tracks outside.
- The Old Dauphin House. Agree to help Pepperidge at Sunken Boxcar.
- Radio Shack. Don Toblerone or Rufus can point you there in one of their quests.
- The Wreck of the Longerfellow. Find your way through Mudhenge to reach it.
Report back to Jessica, and maybe uncurse the key. Sleep to have A Disconcerting Dream.
Day 4 Ongoing Quests
Day 4 booze
- case of whiskey at Moonshiners' Cave
- barrel of tequila at Mob Submarine; set PSI to 19.
- crate of bass oil at Largemouth Bass & Sons
- Rescue Fabien at Gatorman Hamlet and Jeffers at Gatorman Village on day 4 to get a crate of milk the next day at the speakeasy.
Day 4 hobos
- Pepperidge at Sunken Boxcar. You must do his quest to recruit him; see The Old Dauphin House.
- Clyde Mossman at Mossrock Grotto. Talk to the moss-eating kid in the Monster Shack to unlock the location.
- Agamemnon at Gatorman Hamlet. Give him a melee weapon with at least 6 power (modifiers such as sharpening don't count).
These three don't have hobo codes for you until after they arrive at the camp.
Day 4 Mob jobs
Donny has two tasks for you in the swamp.
Rewards: A barrel of tequila and 800 .
Day 4 Rufus aid
Rufus needs you to fiddle with some radio equipment.
Reward: A random ring, if you ask for one.
The Big Moist Side Quests
Get Rasmussen's plane back in the air
Rhonda Rasmussen stands at the foot of a plume of smoke pouring from her plane — presumably a Fokker F.VIIb-3m "Trimotor".
Rewards: 30 and a leather aviator helmet.
Locate Cindy Tracy and Tom Chapman
Bring them back to their terminally self-absorbed fathers at Largemouth Bass & Sons, or better yet, don't.
- 200 , Chapman's doubler, and Charybdis's acceptance.
- 300 , Tracy's impossible rod, and Scylla's approval.
- Both cats, 99 , a judge's wig, and either 45 or 20 fight and Occams Gator's toenail.
Give Paul Leathers a voice
Bring John Leathers five gatorman hides, then five more, then the voice of a gatormerman. Then make, like, a big moral decision or something.
Get the moonshiners back on the road
Find the Schlitz brothers and help them out of a jam.
Rewards: A case of whiskey and 40 .
Retrieve the ancestral padlocks
Pepperidge at Sunken Boxcar wants his father's collection of 11 padlocks. They're ridiculous, and not even funny.
Rewards: 40 and Pepperidge goes to the Hobo Camp. Also find the first all-stat-boosting food in the game, and a strong melee weapon that can become uniquely powerful later.
Discover the secrets of Mudhenge
Find your way to the center of Mudhenge, and....
Remove Will Hunter's arboreal curse
You've always wanted a telescope. Climb up the tree and free Will from being it.
Rewards: 80 and a boy's greatest treasure.
Bring monster trophies to the kids in the Monster Shack
Six kids. Six monsters. Six quests. One cat.
Deal with the Frog God's curse
Wander into The Frogbog and lift a curse. Or worsen it. Or a little of both?
- giant maggot (at once the best and worst hat) and 35 .
- emerald necklace of the Frog God and 35 .
- Mr. Haim the greedy frog and 45 .
Rescue Knows Jeffers from a hypnotizing prison
Go behind the scenes of reality and free the reporter from the Midnight Man's cruelty.
Chapter 5: Heartland of Darkness
Chapter 5 Main Quest
- Do at least one side quest for the people out front,
- At least one for the people inside,
- Then tell Jasper in the office that you're ready. Any of the crew's quests you haven't completed will be abandoned.
- Complete the mission at The Oil Baron's Refinery.
The more crew members you help, the easier the mission will likely be.
- Take the cursed sickle back to Jessica.
As always, uncurse it or don't. The Sickle's Curse awaits you.
Day 5 Ongoing Quests
Day 5 booze
- Get a crate of milk from Fabien and Jeffers at The Purple Door, if you rescued them yesterday.
- Pick up an enchanted ice block at MacMillicancuddy's Farm.
- Swipe an immense can of cocktail onions from The Drexel Stead.
- There's a gallon jug of bitters somewhere in The Moleross Place.
- A five-gallon jar of Maraschino cherries from Grode Valley Orchard.
Day 5 hobos
- Get Beatrice out from among the sheep at MacMillicancuddy's Farm.
- Get Croesus out from behind the vampires at Păpuşășcu Homestead.
- Get Cornelius out from within the corn at The Drexel Stead.
If you've brought at least 10 hobos to the camp, the hobos can help you in the final quest.
Day 5 Mob jobs
Don Toblerone has three final tasks for you. I guess that'd be one antepenultimate task, one penultimate task, and one final task. Anyway, vampires are definitely involved.
Day 5 Rufus aid
Rufus needs you to steal a thing and get your hands dirty.
Gray County Side Quests
- You can get a bunch of neat stuff at The H***hole.
- Beat up Puckwudgie Village for a new addition to Your Room.
Find Wendelin a counterclockwise mainspring
Offer to help Wendelin, outside the feed store. Dig through some normal boxes in the very safe and fine Old Gilmore Place.
Get a glass of milk for Iola
Offer to help Iola, outside the feed store. Buy some stupidly expensive milk at the Maize Maze.
- Iola's reward: 50 } and Iola will dispatch the gate guard at the refinery.
- Location rewards: Bunch of things. See The Drexel Stead.
Retrieve Xenia's paperweight
Offer to help Xenia, outside the feed store. De-duck MacMillicancuddy's farm buildings and return with an item of serious sentimental value.
- Xenia's reward: She will join you in combat at the refinery.
- Location rewards: As much as 90 and maybe some duck loot
Fetch fertilizer for Frover. Grover.
Offer to help Grover, inside the feed store. Grab some fertilizer from Grode Valley Orchard, and maybe also deal with some giant worms.
- Grover's reward: 50 and Grover will blast open the inner wall at the refinery.
- Location rewards: five-gallon jar of Maraschino cherries, Maraschino's Boon, and various wormy loot.
Get Farina a beaned-up engine
Offer to help Farina, inside the feed store. Liberate an experimental engine from The Ford Compound for Farina's Model T limousine.
- Farina's reward: 50 and Farina will provide a quick getaway at the refinery.
- Location rewards: Some more and various beaney loot.
Steal a meteorite for Oskaloosa
Offer to help Oskaloosa, inside the feed store. Twist and turn through The Moleross Place for a really weird rock.
- Oskaloosa's reward: 50 , Oskaloosa's puzzle box, and she will help you get the key at the refinery.
- Location reward: 199 to 570 .
Don't look at the farmer's daughter
Find the Borge House when the driving rain interrupts your wandering. Be cautious; you only get one chance to mess this up.
Set the old mill a-spinnin' again
Converse with the Old Ham Mill, who used to be a library, and soothe its upset feelings.
Resolve the Möbius ring's loop
You should have taken your own advice about the Möbius ring. Wander to Delphine House and wriggle your way out of paradox.
Reward: An Unremarkable Spot on your map and freedom from the ring's curse.
Chapter 6 (Finale): Sinister Enough for Government Work
Chapter 6 Main Quest
Find a letter opener pinning a document to the door of your room.
- As a Pig Skinner, you get a draft registration notice summoning you to the Army Recruitment Office.
- As a Cheese Wizard, you're required to file a wizarding license renewal form at The Shadow D. M. V.
- As a Jazz Agent, an income tax past-due notice instructs you to pay your 13 Meat dues at The Shadow I. R. S.
- Travel to the office you were summoned to and complete the quest there to defeat your nemesis.
- Destroy the three shadow pillars in Government Valley.
- Make your way into The Black House, where you confront The President of Shadows.
- Take the fate of the world into your hands.
After all is said and done, see that fate unfold in the ending.