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It had been a fairly calm fieldtrip, helping the residents in their quests to readjust to society. The only peculiar event was, as they were leaving, a creepy old man, wrinkled with age, looking through a twitching lazy-eye and limping as he walked, stepped up to the bus and placed a black pumpkin with a horrid grinning face on the dashboard. He told them in a cracking, grumbling voice, "Have a happy Halloween."
They thought nothing more of it other than Nurse Dodson telling the driver to get rid of it as soon as they returned to Happytime. Instead, however, things were going to go completely against the normal. As they drove, a strange feeling suddenly overcame them all, such as when one stands up too fast. Their vision darkened, taste buds burned, and skin prickled. When they could see again, they found themselves on a lonely stretch of highway through a forest. Nearby, a sign, with a population number scribbled out and what appears to be a bite taken out of it, read, “Welcome to Halloweentowne.”
Bob becomes confused, and the residents begin to get upset. Nurse Dodson rants at Bob for getting them lost and orders him to drive toward the town ahead to ask for directions. Behind them, Strange Lights appear in the sky and seem to chase them, upsetting the residents further. As they approach town, the lights move stop and move away at impossible speed. Things are quiet from there, other than the bus passing by an armored bank truck driving hurriedly toward the stretch of highway where they had once been.
They come to a gas station, where Bob parks and goes inside for help. He passes through the glass doors, goes around a display of candy bars, and is never seen again. They wait for some time, then people begin to get nervous. Megan tries her cell phone, but there seems to be no service available at all. Moriarty eggs Tad into a fury, and he gets into a tussle with Nurse Dodson and the orderly, ending up with Tad being sedated.
A man in a big 4x4 truck pulls up (instantly nicknamed "Tex"), and Megan asks to borrow his cell phone. He doesn't have one, so she simply asks for directions. None of the places she lists seem to make sense to him, and he simply replies, "Never heard of it" time and again. Apologizing, he heads into the gas station to pay, from where he never returns.
Megan then tries a payphone outside the store. Horrid sounds like squealing dogs come from the dumpster, but she steers clear of it. Dialing 911 and reporting some missing persons, she gets an inept operator who hangs up on her. Calling back, she gets the same operator and is able to talk sense into him this time. Just as he is promising to send a police car around to investigate, a loud voice calls across the line, "You're not supposed to be in here!", and gunshots ring out. The phone line goes dead, and Megan worriedly hangs up.
It becomes apparent that something is very wrong here, and the players make the decision to leave the way they came and maybe meet up with an interstate or something. Nurse Dodson freaks out trying to maintain control, and she sends the orderly in after the driver. When neither return, Megan searches the truck to find a spare key under the bumper and decides to drive off herself. The residents go along, overwhelming the nurse and restraining her over cries that she is in charge.
They drive quickly out of town, the bus in front with James driving (it happened not only to be the same model he drove in the war, but also the very same bus, now that's a luck roll!). Things are quiet until a human-shaped object suddenly pops up in the road, where it is quickly run over. The players stop to investigate, and find a mangled, '30s-style space opera robot. Its parts lunge at them, and the players finish it off. Just as they do, they see red eye-lights of many more robots marching through the trees toward them. Wisely, they climb into the bus and truck and drive away. The robots pursue with a cloud of glowing red lights.
Out on the deserted highway, they eventually see headlights pointed at them. When they swerve into his lane, James swings the bus to miss, but again the headlights play Chicken. He tries to fake a dodge, and the car (a '61 Firebird) sideswipes them, causing a horrid crash with the bus flipping onto its side. Many injuries abound, and Dacia is decapitated as her body was flung halfway through the window just before the bus landed side-down. While she is mourned (especially by Billy), there isn't time to do anything as the Firebird disappears, its red tail lights joining the cloud of lights from the quickly approaching robots.
They pile into the truck, being careful with Nurse Dodson, who suffered a neck injury, drive around the wrecked bus into the ditch, then back onto the highway and away from Halloweentowne. For a while, things seem quiet, then eerily quiet. The trees outside the windows begin repeating conifers and orange deciduous as if they were the background of a poorly funded cartoon chase. Suddenly, the engine of the truck dies, and everything electrical seems simply to shut off. The players have no choice but to climb out of the truck and see what's happening.
While some investigate the engine (finding nothing the matter), Megan pulls her lighter out of her purse and experiments. Where the truck is, the lighter doesn't seem to catch or even spark, but as she walks back toward town, the sparks resume and eventually the lighter lights. Dr. von Haich sets out on foot to investigate. As he walks toward the darkness beyond Halloweentowne, gravity seems to intensify and even pull from behind him. He is forced to his knees, then to his hands, climbing forward as if it were up the face of a cliff. Finally he gives up and, weirded out, returns to the truck. After he explains his findings (who were watching and thought he was just being strange), he and Artie walk out again. This time the pavement seems to soften as they go, soon becoming a quagmire of gray mud and quicksand. They return and announce that leaving what appeared to be the way they came seems futile.
At last they pile back into the truck and head back toward town. The robots have disappeared, and they meet nothing until they return to the gas station on the outskirts of Halloweentowne. They find a delivery truck and a family sedan packed as if for a trip parked at the station, but no one is to be seen. The players set out to search the vehicles for anything that might be of value. As Megan finds the change tray, a dark and mysterious figure approaches from the night. He appears to be an emaciated hobo, his clothes worn, his hair patchy, and his eyes empty of any glimmer of sanity. His nose is raised in the air, sniffing.
The hobo approaches Megan and asks, "Do you have any money?"
Freaked out, Megan gives him all the change she found. He stuffs it into the pockets of his patchy overcoat and asks, "Is that all your money?" Megan empties the cash out her own purse, and he takes the rest of the money. Sniffing again, he looks over the rest of the players, who, as inmates of an insane asylum, have no money, then walks down the sidewalk into the night.
It was then that the boxes in the delivery truck begin moving and screeching. Artie goes berserk and screams for everyone to run away. They fight for a bit, discovering the boxes to be filled with goblins using them like turtle shells. More box-covered goblins pour from the dumpsters, and the players find themselves overwhelmed. Billy is consumed screaming under a pile of twitching boxes. Running back to the truck, they drop matches into a trashcan and leave a gas tank pumping. As they drive away, beating back the goblins that cling to the truck, the gas station explodes, and they hear the dying shrieks of many goblins.
As they come to the intersection that meets the highway, they again pass the armored bank truck. It passes them, then stops and reverses quickly. A man with scraggly hair and a grizzled beard and wearing an overshirt and an old band t-shirt, rolls down his window and motions for them to do the same. Artie, driving, decides to stop and talk.
The man blurts, "Are you from the real world?"
And so the players meet Greg, who takes them back to his house in the nearby Raven Oaks housing edition. He explains the horrors of the annual Halloween night, arms them, takes the injured Nurse Dodson off their hands. They rest for a while, trying to decide where to go look for their Monster. Taking up the newspapers of the past few days (where Greg has circled stories of potential monsters), they come across the note of the famous, supposedly cursed, Sorrow Stone, a white, pumpkin-shaped diamond set in a necklace of platinum and silver. A lord's wife is said to be wearing it as she and her husband stay in the newly renovated Willow Hotel in downtown Halloweentowne. Taking it as a clue, they back into the bank truck and drive toward the center of town.
Driving across Halloweentowne with James at the wheel, they see many strange and horrible events, such as the chaos at the Burger Eats stand, where the doors have been locked and the living hamburgers are chasing and consuming unwitting customers. Moriarty has them stop at a jewelry store, where he and Tad begin smashing cases and filling their pockets. As they begin to hear purring, they look into the shadows to see glowing golden cat's eyes. Their crime-spree comes to a quick end, and they resume their quest to get to the Willow Hotel.
Downtown is in similar chaos. Firefighters battle against what seems to be a living fire consuming a nearby tower. The players decide to choose their battles and make quickly for the hotel, where things seem eerily quiet. James stays with the truck while the others go in to investigate. They enter a grand lobby with wooden floors and art deco decor. To the left, couples are dancing in a ballroom. To the right, the Willow Leaves Lounge holds several people sitting placidly, sipping drinks. Tad hurries into the lounge to get a drink. The players ring the bell at the desk and wait for service.
The wait is too long, and Moriarty crosses over the desk into the back, where he finds a bellboy in the corner crying out for forgiveness from his mother. Gradually, the players realize that something is afoot. The couples dancing in the ballroom are either leaning on one another sobbing or gripping their mates with such terror that their fingernails draw blood. Those in the lounge are drinking themselves into catatonia beyond alcoholism. Dr. von Haich is appropriately weirded out and leaves the building. As he goes back to the truck, someone jumps out of a window, landing directly behind him in a broken heap. James, too, is unnerved now, and the doctor goes wild.
Von Haich takes an RPG launcher out of the truck and sets fire to the hotel. The shock of coming fire seems to be enough to wake some of the people from their madnesses, and the fire escapes are soon filled with people fleeing. The players inside begin hurrying to find the visiting lord and lady's room upstairs, eventually coming across them going insane in their rooms. After some hooplah, they find the lady has stored the necklace in the vault in the basement.
Looking to help his fellow players stall the fire so they can find the necklace and destroy it, Artie steals a fire truck from nearby. As he begins hauling out hoses, a man approaches dressed in early Victorian clothes and soaking wet as if he had just climbed out of a lake. Seeing the body of the fallen man, the Drowned Man goes to it and seems to drink up the spilled blood and all fluid, leaving it a mummified husk. He turns on the doctor as he his helping people escape the burning building, searching for more water to satiate his infinite thirst. James turns the hose on him, and the man is blasted backward, but seems to stand up stronger. The doctor shoots the Drowned Man with a grenade, blowing him through the wall into the lounge of the hotel. Tad, still looking for a drink and embroiled with rage, fights the Drowned Man, punching a hole in the wall next to his head. The man tackles Tad, pouring water out of his mouth to drown him, but, a few grenades later, both are destroyed.
Meanwhile, Artie, Moriarty, and Megan go into the basement with explosives meant for the vault. As they get closer to the vault, their madnesses seem to grow stronger. Artie is terrified into paralysis by a pile of boxes, Moriarty feels rats crawling over his body with tactile hallucinations, and Megan is forced to pop many pills to remain relaxed. Thanks to Megan's medication to keep the madness at bay, they fight themselves forward and blow the door off the safe. When the dust clears, they can see the diamond on its necklace resting on a cabinet inside the gaping vault, and their madnesses seem to explode. Moriarty feels as if his skin is peeling itself off, Megan goes mad for want of more pills, and Artie screams for a long time. Eventually, they approach the necklace again and attack it with a hammer, breaking it in half after a few strikes. The smaller of the halves turns to white ash. Its power weakens, and they break it into half again.
Realizing that they'll only end up with smaller and smaller diamonds, they pick up the diamond and carry it to the truck to find something else. They meet with James and the doctor, whose paranoia suddenly sparks. The evil of the diamond focuses its remaining power on corrupting the doctor's senses, telling him the others are just against his discovery and study of such a mythic object. He seizes the diamond and runs into the night.
The others take up pursuit in the bank truck. They have to go around where the doctor had gone on foot, but eventually they catch up to him, face-to-face with a short, ugly man in a green suit. The leprechaun has hypnotized Chad to be a slave in his mines and takes the diamond from him to add to his treasure. Moriarty bargains with him, finally getting the diamond back in exchange for some of the jewelry in his pockets, though he decides not to trade something for Chad himself.
Just as things seem to go well, a fifty-foot alligator comes around the corner. It lunges at Chad, and the leprechaun makes an enormous Irish dragon illusion to defend himself. He cackles about how fun this is, while the players run inside the bank truck for protection. A swipe from the giant reptile's tail throws the truck onto its side.
Then the horde of zombies comes. The players try to fight them at range with the weapons from the truck, but the diamond affects their minds, causing them to lose their will to fight. Soon the zombies overwhelm them, and they are trapped inside the armored truck, undead hands pounding on every window trying to get inside. Fighting the throes of the diamond, they set to destroying it, and finally manage to injure it by pouring holy water onto it. Artie sees its weakness and stuffs the weakened evil jewel into the canteen of holy water itself, where there is an unearthly cry and dark steam rushing out, clouding the eyes of all the players.
When they can see again, they find themselves on the highway where they last remembered being in the real world. The bodies of Dacia, Billy, and Tad lie around them, along with the wrecked bus still on its side. Moriarty checks his pockets, but the jewelry in his pockets seems to be gone along with everything else from Halloweentowne. Still, he decides he has his freedom as a reward and begins simply walking away. The other patients tend to the braced and screaming Nurse Dodson and wait to be picked up and returned to their quiet sanitarium.