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This is a setting with a creepy motif. The buildings are gothic in design (often clearly modeled on The Cabinet of Dr. Caligari), there's always a heavy fog in the air that obscures your vision, and the full moon always lights the cloud-draped sky... even at 2:30 in the afternoon. Halloweentown is usually inhabited by the usual assortment of horror trope creatures. The main color schemes are black, gray, orange, red, and black and slimy green, and black... sometimes in combination.
Despite the somber colors and the Horror Trope decor, this setting is not always played solemnly. Imagine the Perky Goth or Nightmare Fetishist character as a setting, and you've got this place. It's less Eastern European and more trick or treat. Halloweentown is usually not that scary, at least not intentionally so. It's intended to be somewhat playful and fun. A good way to tell if a series is set in a place like this is if there are jack-o-lanterns and it's not Halloween, although it's not a prerequisite.
- The independent comic series Underburbs. Countess Winifred Pale, a vampire, begins a world domination plot by turning a small human town into part of an evil dimension, transforms residents into monsters and effectively makes every day into Halloween.
- The Trope Namer is The Nightmare Before Christmas. It is the job of the inhabitants of Halloweentown to make Halloween happen each year.
- Corpse Bride, the spiritual successor to The Nightmare Before Christmas, takes place in this sort of setting as well.
- The Halloweentown series of movies. The titular town is unusually bright and cheery... Until it's time for bed...
- Or when Kal turned it into a gray bland location as part of his agenda of avenging his old man and namesake in the second film.
- The world Other-Mother creates in Coraline.
- Also subverted, in that it's a death trap.
- Out Run 2006 has one of these scenarios as race track.
- A proto-example is Holstenwall from The Cabinet of Dr. Caligari. It has the creepy mood and architecture (which were a visible inspiration for Nightmare), but only one Mad Scientist and his sleep-walking Serial Killer.
- This trope is the entire point of The Addams Family, along with the similarly themed show, The Munsters.
- Animal Crossing has the Spooky furniture set, which can only be found on--of course--Halloween. It allows you to turn your house into one of these.
- Mad Monster Mansion in Banjo-Kazooie.
- Croatoa, a zone in City of Heroes, is fog-encrusted, and inhabited by ghosts, witches, Red Caps, and fire-breathing Jack-o-Lantern plant monsters.
- Horrorland in the Goosebumps point and click adventure game Escape from Horrorland.
- Conkers Bad Fur Day has the aptly-titled Spooky level, which seems to be this, except there actually are flesh-eating zombies and vampires that you have to kill.
- The Netherworld/Makai in every iteration of Disgaea and its sister series.
- Donkey Kong Country 2 has one of these.
- In Kingdom Hearts, the protagonists actually visit the trope-naming town a couple of times.
- Haunted House on the Atari is one of the first games to be set here.
- Ooga Booga Land in King's Quest VII.
- The entirety of Luigis Mansion.
- The final world of New Super Mario Brothers has a distincty Halloweeny feel. And walking Pumpkins.
- Twilight Town in Paper Mario the Thousand Year Door exists in a state of perpetual twilight, with a gigantic yellow full moon in the sky, and is inhabited mainly by crows and the gothic Twilighters.
- Dark City (Chaos Faction) in the somewhat obscure MMO Angels Online.
- Niffleheim in Ragnarok Online.
- The original Niflheim was the frozen underworld of Norse mythology.
- Pumpkin Hill, Aquatic Mine, and several other levels in Sonic Adventure 2.
- Super Mario Land 2 has the Pumpkin Zone.
- Super Mario World has an unlockable skin that turns the game into this if you can beat the special stages.
- World of Warcraft's Undercity, home of the Forsaken undead. This is a city built completely underground. All the buildings are gothic in design, skull-shaped decorations abound. Green-yellow goo (in which you can surprisingly fish) flows in the canals. The city is guarded by giant abominations (read Frankenstein's Monsters). One of the quarters of the city is "The Apothecarium": a laboratory destined to the production of said monsters and the development of new Plagues. All the inhabitants are obviously undead. The ruler is a Banshee and the co-ruler (used to be, until his failed takeover attempt) a vampire-demon. This is the actual capital city for a player race, too. Not a vile dungeon you need to destroy. (Don't get us wrong, the Forsaken are mostly massive assholes, especially the Apocrathary, but still.)
- As far as actual dungeons are concerned, Naxxramas probably qualifies. A flying Necropolis filled with more indead horrors your mind can comprehend.
- There is also the halloween-feel to Duskwood from Darkshire to the Worgan raids. The whole area also often plays host to the Headless Horseman, Pumpkin Fest, and Trick or Treat Mask give-aways every year.
- Ghost Island in Pac-Man World.
- Crescent Moon Village from Wario Land 4 has this feel about the place, as well as being Big Boo's Haunt.
- Underworld from Fallout 3 is the closest the setting can offer. It's a settlement of ghouls (in the Fallout universe, this refers to ageless Technically Living Zombies who're usually sapient and got their condition from being massively irradiated) who took up residence in a museum exhibit about the afterlife, hence the name and the giant stone skull over the gate. Many of the people and places in there have names relating to death and mythological interpretations of the afterlife.
- The "Wacky Worlds" expansion pack of Rollercoaster Tycoon 2 lets you put Halloween and "horror"-themed decorations in your park, along with the option of bare dirt (or whatever you want) for the ground. Some rides are even Halloween themed.
- The Transylvania world in Looney Tunes Bugs & Taz Time Busters.
- The town of Threed in Earthbound at least before you beat Master Belch, it features zombie dogs, zombies, ghosts, a graveyard, coffins in an underground path leading to Grapefruit falls, and even a totally blatant Halloween enemy called the Trick or Trick kid.
- The Neitherworld in the animated adaptation of Beetlejuice. It's full of bizarre buildings, gothic looking scenery, twisted backgrounds, and strange creatures of all shapes and sizes. Of course, the creatures are, for the most part pretty friendly if a little strange.
- Casper's Scare School has its school here.
- Ruby Gloom is set here.
- The entirety of the Anur star system Ben 10: Omniverse, its Hubworld of Anur Transyl in particular.
- Certain parts of Salem Massachusetts try SO hard to live this trope year-round. Unfortunately, the bar, or ice cream shop, or convenience next door conveniently ruins the illusion.