Shadows over Loathing quests

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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 XP, 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 XP, grab the terribly cursed fedora, and return to the antique store.

  • Talk to Jessica.

She strongly urges you to remove the curse from the fedora. You can do so, leave it for later, or just keep it cursed forever. See uncursing machine.

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 Meat. 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.

He says Oliver Gluck, the owner, is the only one with a watch, and he went to pick up hooch from the Refrigerator Factory. He gives you an Ocean City napkin map, unlocking your ability to travel.

At the Refrigerator Factory, you find some mob guys blocking your way. They demand 500 Meat 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.

When it is defeated either way, you find the dangerous pocketwatch you were looking for, a pouch of Meat, and a deed to the Speakeasy.

  • Return the deed to Fancy Dan to become owner of the Speakeasy.
  • Then return to the antique store and speak with Jessica.

You can use the uncursing machine to transform The Watch's Curse. Like the fedora, you may choose not to uncurse it; it is a powerful tool in combat, after all.

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.

Day 1 Ongoing Quests

Find booze for the speakeasy

Main article: The Purple Door

Throughout the game, you can find additional booze and other ingredients for your speakeasy, giving you more and better options for your booze buff.

Barnaby, a blind man drinking alone, provides cryptic hints to help you find ingredients. He refuses to speak to you with Shadow taint level 3 or higher.

Today, just one new bar material is available:

Bring people to the Hobo Camp

Main article: 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 XP 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 Meat 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 Meat to get him on the road and into the camp.
  • Give Dusty 5 Meat 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 Meat on new stuff and XP on new skills as you explore the city and complete quests.

You probably want to grab your class skill books too. Find them:

Do contractor work at Goldthwait Park

Main article: 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 Meat, 30 XP (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.

Reward: The easiest 10 XP of your life.

Test some dubious grenades for Cola Wars Surplus

Main article: Cola Wars Surplus

The fella at Cola Wars Surplus is happy to pay you to probably get yourself killed.

Reward: 200 Meat and 10 XP.

Get your fortune told for some reason

When you have 150 Meat to spare, get your fortune at Ocean City Boardwalk three times.

Reward: Skeptical, a perk for +1 Mysticality. This plus St. Polycarp's and Marvin's quests add up to a permanent +1 to all stats.

Find the missing cremains for St. Polycarp's

Find St. Polycarp's Cathedral in Ocean City wander events..

Rewards: St. Polycarp's Forehead (a perk for +1 Muscle) and Ishmael's Boon for +1 Mysticality.

Find some Snackle Cakes for Marvin

Main article: Marvin's Mailbox

While wandering, you may spot a man sitting on a mailbox — Marvin's Mailbox. Bring him some snacks.

Rewards: Expert Sitter (a +1 Moxie perk) and 100 Meat.

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.

Rewards: FOOTS ring, 10 XP, a nice rug for Your Room, and possibly 16-25 Meat and/or an achievement.

Investigate Ernst Zimmer's incredibly haunted house

Main article: Ernst Zimmer's 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 XP, and the continued safety of the world, at least for a little while.

Alternate reward: rift crystal. Get a really nice amulet made from the crystal later, if you pick Rodkin Fine Jewelry as one of your new neighbors.

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.

Doughboys: If you haven't found their Snackle Mills hideout via Marvin's quest, the boys drop a Doughboys hideout recipe after a fight or two in the streets. Read it to put the hideout on your map.

Rewards: Ciabatta's pants, some mana-enriched flour, ~75 Meat, and the recipe for the dough baby familiar, plus 12-17 fight XP.

Glocklins: Fight them a couple times in wandering events and the enbies drop a Glockenspielery flyer. Use it to get Gideon's Glockenspielery on your map.

Rewards: 200 Meat, 12 fight XP, 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 XP; 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 XP (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.

Day 2 Ongoing Quests

Day 2 booze

Main article: The Purple Door

Day 2 hobos

Main article: Hobo Camp

Work for the Mob

Main article: Don Toblerone

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.

Reward: 700 Meat, and lots more in the future.

Crystaldream Lake Side Quests

Save the Village of Sandwich

Main article: Sandwich Museum

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 XP, a twinkling crystal statuette, and access to Crystal's crystals.

Get Worms for Grady

Help Grady stock up his shop.

Rewards: 100 Meat, a potted nightcrawler, Dottie's Boon, and you can buy a worm familiar.

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.

Day 3 Ongoing Quests

Day 3 booze

Main article: The Purple Door

Day 3 hobos

Main article: Hobo Camp

Day 3 Mob jobs

Main article: Don Toblerone

Don T. has three tasks for you at S.I.T.

Reward: 1800 Meat

Help Rufus find his sibling

Main article: S.I.T. (Rufus's Lab)

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

You can also ask the janitor about the Vector Wing to uncover a hobo code there.

Find some barbecue sauce for Floyd

Check the notices board at S.I.T. (Barbecue Wing) to unlock Fission Chips.

Get some wood chips for a cuein' frat guy

Main article: Zeta Omega Omicron

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.

Reward: 25 XP

Get a lost jacket for a chilly frat guy

Main article: Phi Upsilon Tau

Check a notice board in S.I.T. (Spider Wing) to mark Zeta Omega Omicron on your map. Walk to the right from there to reach Phi Upsilon Tau. The shivering guy needs his jacket.

Reward: 10 XP

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 XP.

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:

Examining the three campsites unlocks Charles's location. See Gatorman Fortress for steps to find the cursed key and rescue Charles.

Report back to Jessica, and maybe uncurse the key. Sleep to have A Disconcerting Dream.

Day 4 Ongoing Quests

Day 4 booze

Main article: The Purple Door

Day 4 hobos

Main article: Hobo Camp

These three don't have hobo codes for you until after they arrive at the camp.

Day 4 Mob jobs

Main article: Don Toblerone

Donny has two tasks for you in the swamp.

Rewards: A barrel of tequila and 800 Meat.

Day 4 Rufus aid

Main article: S.I.T. (Rufus's Lab)

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

Main article: Crash Site

Rhonda Rasmussen stands at the foot of a plume of smoke pouring from her plane — presumably a Fokker F.VIIb-3m "Trimotor".

Rewards: 30 XP 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.

Possible rewards:

Give Paul Leathers a voice

Main article: The Leathers Brothers

Bring John Leathers five gatorman hides, then five more, then the voice of a gatormerman. Then make, like, a big moral decision or something.

Rewards: 40-49 XP, plus either valuable hunting knife and magnifying glass, or the Disarmer Armor perk. Disarmer armor.

Get the moonshiners back on the road

Main article: Moonshiners' Shack

Find the Schlitz brothers and help them out of a jam.

Rewards: A case of whiskey and 40 XP.

Retrieve the ancestral padlocks

Main article: The Old Dauphin House

Pepperidge at Sunken Boxcar wants his father's collection of 11 padlocks. They're ridiculous, and not even funny.

Rewards: 40 XP 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

Main article: Mudhenge

Find your way to the center of Mudhenge, and....

Rewards: A lot of XP, a lot of Meat, some cool stuff, and maybe a hidden achievement.

Remove Will Hunter's arboreal curse

Main article: Treehouse

You've always wanted a telescope. Climb up the tree and free Will from being it.

Rewards: 80 XP and a boy's greatest treasure.

Bring monster trophies to the kids in the Monster Shack

Main article: Monster Shack

Six kids. Six monsters. Six quests. One cat.

Possible rewards: 210 or more XP, a Phlemberg familiar, Monster Club sash, and Boris's Boon.

Deal with the Frog God's curse

Main article: Haim Quarry

Wander into The Frogbog and lift a curse. Or worsen it. Or a little of both?

Possible rewards:

Rescue Knows Jeffers from a hypnotizing prison

Main article: Gatorman Village

Go behind the scenes of reality and free the reporter from the Midnight Man's cruelty.

Reward: If you rescue him and Fabien (in the Cathy and Tom quest) both on Day 4, they'll be at The Purple Door on Day 5. Talk to them for a crate of milk.

Chapter 5: Heartland of Darkness

Chapter 5 Main Quest

Jessica's weird machine points you toward a cursed sickle in Gray County. To get at it, you must help the nice people at Jasper's Feed and Tack get their revolution on.

  • 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.

As always, uncurse it or don't. The Sickle's Curse awaits you.

Day 5 Ongoing Quests

Day 5 booze

Main article: The Purple Door

Day 5 hobos

Main article: Hobo Camp

If you've brought at least 10 hobos to the camp, the hobos can help you in the final quest.

Day 5 Mob jobs

Main article: Don Toblerone

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.

Rewards: 1039 Meat, Expensive Luxuries, Inc. catalog, rescue for Croesus the hobo, a mob capo signet, and the Mob can help you in the final quest.

Day 5 Rufus aid

Main article: S.I.T. (Rufus's Lab)

Rufus needs you to steal a thing and get your hands dirty.

Rewards: 55 XP, and Rufus can help you in the final quest.

Gray County Side Quests

Find Wendelin a counterclockwise mainspring

Main article: The Old Gilmore Place

Offer to help Wendelin, outside the feed store. Dig through some normal boxes in the very safe and fine Old Gilmore Place.

Reward: 50 XP and Wendelin will get the gate open at the refinery.

Get a glass of milk for Iola

Main article: The Drexel Stead

Offer to help Iola, outside the feed store. Buy some stupidly expensive milk at the Maize Maze.

  • Iola's reward: 50 XP} 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 XP and maybe some duck loot

Fetch fertilizer for Frover. Grover.

Main article: Grode Valley Orchard

Offer to help Grover, inside the feed store. Grab some fertilizer from Grode Valley Orchard, and maybe also deal with some giant worms.

Get Farina a beaned-up engine

Main article: The Ford Compound

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 XP and Farina will provide a quick getaway at the refinery.
  • Location rewards: Some more XP and various beaney loot.

Steal a meteorite for Oskaloosa

Main article: The Moleross Place

Offer to help Oskaloosa, inside the feed store. Twist and turn through The Moleross Place for a really weird rock.

  • Oskaloosa's reward: 50 XP, Oskaloosa's puzzle box, and she will help you get the key at the refinery.
  • Location reward: 199 to 570 Meat.

Don't look at the farmer's daughter

Main article: Borge House

Find the Borge House when the driving rain interrupts your wandering. Be cautious; you only get one chance to mess this up.

Reward: a farmer's daughter's necklace, a farm towel, or nothing

Set the old mill a-spinnin' again

Main article: Old Ham Mill

Converse with the Old Ham Mill, who used to be a library, and soothe its upset feelings.

Reward: 50 XP

Resolve the Möbius ring's loop

Main article: Delphine Farmhouse

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

There are no new hobos to meet, Mob contracts to complete, or tasks to help Rufus with in the final day. Finish up any that remain if you want their help for the main quest.

There are no new side quests either, nor booze for The Purple Door. However, Charlestown State Pen is full of useful people and helpful items. Perhaps even the other way around.

Chapter 6 Main Quest

Main article: The Black House

Find a letter opener pinning a document to the door of your room.

It's an obvious trap, but Jessica needs you to go to Government Valley anyway, to find a powerful curse... thing of unknown (un)nature. She hands you a Map, an actual map, of Government Valley.

  • Travel to the office you were summoned to and complete the quest there to defeat your nemesis.
Main article: Charlestown State Pen
Main article: The Shadow D. M. V.
Main article: The Shadow I. R. S.
  • Destroy the three shadow pillars in Government Valley.
Main article: Shadow pillar

After all is said and done, see that fate unfold in the ending.