JACK-O’s 31-Day Halloween Movie Challenge: Streaming Guide (October List #1)

My 31 day movie watchlist for this month, one week late. I took Dread Central's 31 Day Horror Movie Challenge for October 2018 and added, removed or moved around some films to create my list, click on the image above or check out the list of movies with links where to stream them online below (some free with ads).

My 2018 31 Day Horror Movie Challenge with links to where they are streaming online most free:

10/1:	On Halloween night, a babysitter discovers a mysterious VHS tape that unleashes a series of brutal encounters with the sadistic clown Art and other nightmarish figures. A grim VHS horror tape where Art the Clown proves he’s less a character and more a warning label you really should’ve listened to. All Hallows’ Eve (2013) streaming on Tubi, Roku On Halloween night, a cursed VHS tape unleashes a series of interconnected horror stories involving demonic forces, killers, and supernatural terror targeting unsuspecting victims. An Art the Clown-less follow-up anthology that doubles down on the cursed-tape chaos—because apparently pressing play on Halloween is a legally binding death wish. All Hallows’ Eve 2 (2015) streaming on Tubi, Roku, Plex On Halloween, a group of unsuspecting victims encounters a mischievous supernatural entity known as the Trickster, whose games quickly turn deadly and inescapable. A modern Halloween horror where the Trickster doesn’t just play games—he makes sure you never get to finish the round. All Hallows Eve: Trickster (2023) streaming on Tubi On Halloween night, a new batch of cursed stories pulls unsuspecting victims into a series of hellish encounters, as a demonic force orchestrates increasingly brutal trials of survival. A fiery follow-up that turns the franchise into a one-way descent straight through Halloween and into full-blown hell. All Hallows Eve: Inferno (2024) streaming on
10/2:	On Halloween night, two friends are relentlessly stalked by the sadistic Art the Clown, whose night of terror spirals into increasingly brutal and unhinged violence. A no-holds-barred gore fest where Art the Clown turns Halloween into a silent, sadistic show—and he’s the only one enjoying it. Terrifier (2017) streaming on Tubi, Roku, Plex Resurrected and more vicious than ever, Art the Clown returns on Halloween night to terrorize a teenage girl and her brother, unleashing an extended spree of brutal, supernatural carnage. A sequel that goes bigger, gorier, and longer—because apparently Art the Clown heard “too much” and took it as a challenge. Terrifier 2 (2022) streaming on Tubi, Plex, Pluto Art the Clown returns during the Christmas season to continue his reign of terror, targeting survivors from the past while spreading his sadistic chaos beyond Halloween. A holiday horror curveball where Art swaps pumpkins for a Santa suit, proving Christmas is just another excuse to be absolutely monstrous. Terrifier 3 (2024) streaming on
10/3:	On Halloween night, a group of townspeople awaken a demonic Harvest Lord tied to an ancient curse, unleashing violent supernatural forces that begin claiming victims one by one. A grim Halloween outing where the harvest comes early—and it’s collecting souls, not crops. All Hallows Evil: Lord of the Harvest (2012) streaming on YouTube
10/4:	On Halloween night, a woman uncovers a disturbing ritual involving possession, murder, and a cult tied to a spider-like supernatural entity. A creepy Halloween descent where the real nightmare isn’t spiders—it’s realizing you’ve already been caught in the web. Honeyspider (2014) streaming on YouTube, YouTube, Tubi
10/5:	On Halloween night, a cursed scarecrow-like pumpkin-headed killer is accidentally resurrected and goes on a rampage against a group of teens and their families. A gloriously chaotic B-movie where the pumpkin-headed menace looks less like pure evil and more like Halloween décor that came to life with a grudge. Jack-O (1995) streaming on
10/6:	A group of friends at a Halloween party are hunted by a masked killer who recreates brutal murders inspired by real-life snuff films. A Halloween rampage that ends on such a grim note, it leaves you sitting through the credits with some very uncomfortable thoughts. Carver (2015) streaming on Tubi, Plex
10/7:	A young man becomes entangled in his grandfather’s sinister satanic cult, which uses Halloween celebrations as a cover for ritualistic murders and dark occult ceremonies. A gloriously weird 80's relic where every pumpkin feels like it’s moments away from crashing a satanic Halloween party you definitely weren’t invited to. Hack-O-Lantern (1988) streaming on Tubi, Archive
10/8:	A series of interconnected Halloween-themed horror stories unfolds in a small town, where students and residents become victims of killers, curses, and supernatural revenge. An indie horror anthology where Halloween isn’t just a night of scares—it’s basically the town’s unofficial death announcement. Volumes of Blood (2015) streaming on Tubi, Roku, Plex An expanded anthology of Halloween horror stories connects multiple tales of killers, curses, and supernatural terror across a town plagued by escalating violence. A sequel that cranks up the carnage, proving this town doesn’t just have a Halloween problem—it has a full-blown storytelling curse. Volumes of Blood: Horror Stories (2016) streaming on Tubi
10/9:	A masked killer, Michael Myers, escapes a mental institution and returns to his hometown on Halloween night to stalk and murder babysitters, particularly Laurie Strode. The film that turned “someone watching you from the shadows” into Halloween’s most enduring—and relentlessly silent—problem. Halloween (1978) streaming on Archive
10/10:	After surviving Michael Myers’ attack, Laurie Strode is taken to a hospital where the relentless killer continues stalking her through the night while a shocking family connection is revealed. A sequel that proves even hospital security can’t stop Michael Myers—he really does follow you into every sequel like a billing charge you can’t escape. Halloween II (1981) streaming on Archive, Archive, Archive
10/11:	A doctor investigates a sinister mask-making company whose Halloween products are tied to an ancient pagan ritual designed to kill millions of children on Halloween night. The one Halloween movie without Michael Myers—and the one that dares to ask what if the real killer was corporate holiday marketing... and masks that melt kid’s faces. Halloween III: Season of the Witch (1982) streaming on Archive
10/12:	After years in a coma, Michael Myers awakens and returns to Haddonfield to hunt down his young niece, forcing the town to confront his renewed killing spree. A sequel that proves Michael Myers doesn’t need an invitation—he just shows up like the world’s most persistent family reunion nobody asked for. Halloween 4: The Return of Michael Myers (1988) streaming on YouTube
10/13:	One year after the massacre, Michael Myers returns to continue hunting his young niece Jamie, while a mysterious figure in black suggests a darker force guiding his actions. A sequel where Michael Myers proves he doesn’t just come back—he comes back with confusing new lore and absolutely zero interest in being stopped. Halloween 5: The Revenge of Michael Myers (1989) streaming on
10/14:	Six years after his disappearance, Michael Myers resurfaces as part of a sinister cult’s plan involving his family bloodline and a mysterious “curse” that drives his killing spree. A sequel that turns Michael Myers into the centerpiece of a lore-heavy cult conspiracy—because apparently unstoppable evil needed a very complicated backstory. Halloween: The Curse of Michael Myers (1995) streaming on
10/15:	Two decades after surviving Michael Myers’ original rampage, Laurie Strode lives in hiding until he reappears, forcing her into a final confrontation on Halloween night. A sleek ‘90s reset where Laurie finally says “enough sequels” and decides to end the franchise the old-fashioned way—by confronting it head-on. Halloween H20: Twenty Years Later (1998) streaming on
10/16:	Michael Myers returns to his childhood home where a reality TV crew livestreaming from the house becomes his next group of unsuspecting victims. A sequel that turns Halloween into early-2000s internet bait—because nothing says terror like being live-streamed while Michael Myers crashes the broadcast. Halloween: Resurrection (2002) streaming on
10/17:	A reboot that reimagines Michael Myers’ origins, tracing his troubled childhood and psychological descent before he escapes captivity and returns to Haddonfield as an unstoppable killer. Rob Zombie’s gritty origin story that insists Michael Myers needed a backstory—and then makes sure you sit through every dark, sweaty, profanity-laced detail of it. Rob Zombie's Halloween (2007) streaming on After surviving Michael Myers’ attack, Laurie Strode struggles with trauma and disturbing visions while Michael continues his brutal killing spree as their psychological connection deepens. A sequel that trades stalking for trauma spirals, proving even Michael Myers can’t escape Rob Zombie’s commitment to turning horror into therapy session chaos. Rob Zombie's Halloween II (2009) streaming on Archive, Tubi
10/18:	Decades after his original killing spree, Michael Myers escapes captivity and returns to Haddonfield, where Laurie Strode prepares for a final confrontation with her lifelong tormentor. A legacy sequel where Laurie didn’t just survive trauma—she turned it into a home security system with a very personal grudge. David Gordon Green's Halloween (2018) streaming on As Michael Myers continues his killing spree in Haddonfield, the townspeople band together in a violent mob while Laurie Strode and her family grapple with survival and escalating chaos. A middle chapter where Haddonfield discovers the hard way that forming an angry mob doesn't mean you're easily stopping Michael Myers. Halloween Kills (2021) streaming on Years after the killings, Laurie Strode tries to rebuild her life while a new young man becomes entangled in Michael Myers’ lingering influence, leading to a final confrontation that ends their long-running conflict. A finale that trades relentless stalking for existential detours, suggesting that Evil doesn’t die—it changes shape. Halloween Ends (2022) streaming on
10/19:	On Halloween night, a group of teens accidentally awakens an ancient curse that brings vampires, zombies, and witches to life in their small town. A ‘80s Halloween TV-movie where the only thing more overstuffed than the monster roster is the sheer joy of watching the whole town descend into spooky chaos. The Midnight Hour (1985) streaming on YouTube (VHSrip with commercials), YouTube (DVDrip), YouTube (1080 Upscaled)
10/20:	A lonely man is lured to a Halloween “murder party” where a group of pretentious artists plan to kill him as part of an art project that quickly spirals out of control. An indie horror-comedy where the real masterpiece is how quickly “performance art” turns into everyone realizing they are wildly unqualified for murder. Murder Party (2007) streaming on
10/21:	A group of carnival workers is kidnapped on Halloween and forced to survive a deadly game called “31,” where they are hunted by masked killers for twelve hours of sadistic entertainment. A grim carnival ride where the only prize is survival—and the only rule is that Rob Zombie is absolutely going to make it as chaotic as possible. Rob Zombie's 31 (2016) streaming on Tubi, Plex, Pluto TV
10/22:	A bullied teenager accidentally brings his deceased rock star idol back from the dead through a cursed record, unleashing supernatural chaos on his high school on Halloween night. A metal-fueled ‘80s fever dream where the real trick is how quickly revenge, rock music, and demonic energy all turn up to eleven. Trick or Treat (1986) streaming on Screambox, Cineverse, YouTube
10/23:	On Halloween night in 1989, a group of teens accidentally awaken three murderous creatures trapped inside an abandoned barn, unleashing a retro-styled slasher nightmare on their small town. A love letter to ‘80s horror where the barn isn’t just haunted—it’s basically a permanent Halloween attraction run by monsters waiting to drag you straight to hell. The Barn (2016) streaming on Tubi, Roku, YouTube Years after the original massacre, new victims stumble upon the cursed barn and its surviving demonic killers, reigniting the Halloween horror in another blood-soaked night of chaos. A sequel that proves some barns don’t need repairs—they need an exorcism and a very firm “do not reopen on Halloween” notice. The Barn Part II (2022) streaming on
10/24:	On Halloween night, a group of teens throwing a party in an abandoned funeral home accidentally awakens demonic forces that begin possessing and slaughtering them one by one. An ‘80s hell party where the guest list is fine—until the demons show up and turn “stay the night” into a literal death sentence. Night of the Demons (1988) streaming on Pluto TV, YouTube A group of Catholic school students sneak out to a haunted funeral home on Halloween, where they inadvertently unleash demonic forces that begin possessing and killing them. A sequel that proves curiosity and haunted funeral homes are a terrible mix—especially when the demons are still very much in party mode. Night of the Demons 2 (1994) streaming on Internet Archive On Halloween night, a group of teens fleeing from the law take refuge in the cursed funeral home, where the demonic presence is reawakened and begins possessing and killing them. A low-budget sequel where the demons are still partying like it’s Halloween 1988—only now the guest list is shorter and the chaos is even more committed. Night of the Demons 3 (1997) streaming on YouTube On Halloween night, a group of partygoers trapped inside a haunted mansion unwittingly awakens demonic forces that possess and brutally kill them one by one. A glossy remake that cranks the chaos up to eleven—because nothing says “modern update” like demons who are still very committed to ruining Halloween. Night of the Demons (2009) Remake streaming on Tubi
10/25:	A rational constable is sent to investigate a series of decapitation murders in the village of Sleepy Hollow, where he uncovers a dark mystery involving superstition, revenge, and the legendary Headless Horseman. A gothic Tim Burton mystery where even the "Tree of the Dead" gets more unsettling screen presence than most modern horror villains. Sleepy Hollow (1999) streaming on
10/26:	This anthology series follows different eerie Halloween-season tales where ordinary people encounter curses, hauntings, and supernatural forces that blur reality and nightmare. A cozy seasonal scare-fest where every story feels like autumn leaves... if autumn leaves occasionally tried to kill you. The Witching Season (2015- ) streaming on Tubi, Plex, YouTube
10/27:	On Halloween night in 1997, two estranged teenage skaters reconnect while walking home through their suburb, encountering surreal visions that blur memory, guilt, and reality. A moody Halloween trip where the real scare isn’t what’s in the trees—it’s everything the past refuses to let go of. Boys in the Trees (2016) streaming on YouTube
10/28:	On Halloween night, a series of eerie encounters unfolds as three mysterious trick-or-treaters bring unsettling consequences to anyone who crosses their path. A stripped-down no dialogue Halloween chiller where the candy is scarce, the vibes are ominous, and the trick-or-treaters are definitely not stopping for fun-size anything. 3 Dead Trick or Treaters (2016) rent at Videonomicon
10/29:	Presented as a live BBC broadcast on Halloween night, a paranormal investigation into a supposedly haunted house spirals into terrifying and uncontrollable supernatural events. The ultimate “don’t trust live TV on Halloween” experiment—where the broadcast starts as journalism and ends as pure national nightmare fuel. Ghostwatch (1992) streaming on Internet Archive A faux 1980s VHS recording of a TV news broadcast and a Halloween night investigation into a supposedly haunted house, blending staged interviews, commercials, and escalating paranormal claims. A perfect analog Halloween time capsule where the real horror is realizing how convincing late-night local TV used to be. WNUF Halloween Special (2013) streaming on Facebook
10/30:	On Halloween night, a pregnant teenager is trapped at home and terrorized by eerie, otherworldly children whose visits escalate into a surreal fight for survival. A feverish Halloween nightmare where the doorbell keeps ringing—and every “trick-or-treater” looks less like a kid and more like a warning you should’ve answered differently. Hellions (2015) streaming on Roku, Plex, Pluto TV
10/31:	On Halloween night in a suburban town, several interconnected stories unfold as trick-or-treaters, pranksters, and monsters collide under the watchful rules of Sam, a mysterious enforcer of the holiday. A perfectly twisted Halloween anthology where breaking tradition doesn’t just ruin the night—it guarantees Sam shows up to correct your behavior permanently. Trick ‘r Treat (2007) streaming on A Halloween anthology film set in a suburban town, where multiple interconnected stories follow trick-or-treaters, killers, and supernatural threats unfolding across one chaotic night. A candy bowl of horror shorts where every handful is a different flavor of Halloween chaos—and some of them definitely bite back. Tales of Halloween (2015) streaming on Tubi, Roku, Plex

Youtube Playlist of Trailers:

Orange and Black Posters Animated GIF: