Hi /u/yankolo, I'm not exactly sure what you're asking as this is a pretty general question but I've taken a stab at giving some insight at least at a literary level.

There is an undeniable relationship in the popular consciousness between Halloween and the Gothic. The biggest similarity, I think, is spooky things. Weird things. Strange things. Film most likely has had the biggest effect on cementing this idea, though. I’m not exactly certain why horror films have always been popular to produce, but even back to the silent era with films like Häxan and Nosferatu (an unauthorized version of Dracula, to boot) and the later Universal Classic Monsters, 20th century children have always had a healthy stable of grotesques to choose from when planning their Halloween costumes.

‘Guising,’ as it was called, had always been part of the Halloween tradition, but by the 1930’s costumes were being mass produced—and there definitely were Draculas, Wolfmen, and more running around. I do think it’s a simple, but understandable connection to make—Gothic novels were some of the easiest and most popular stories to adapt into film when it came to making something scary, exciting, and money-making. Then when Halloween rolled around, these monsters made the perfect choice for a costume—and thus started the proliferation of Gothic atmosphere and clichés into Halloween decorations and festivities. There’s more these two subjects have in common than just at a surface level, though.

The roots of Halloween, of course, go back to pagan ritual practices of the Celts. When Christianity arrived in the British Isles, as happened with so many other places, it was decided to incorporate the local customs into Christian practices in order to convert as many people as possible. With the Christians celebrating All Saints day on November 1st, the feast of Samhain on October 31st developed into All Hallows’ Eve.

Historically, it was a religious holiday—it wasn’t until about the 18th century when the more modern concept of Halloween began to emerge. Halloween was always saturated in ritualistic practices and folklore, but this century saw that aspect of superstition incorporated more into the forefront of the celebration by way of apple bobbing, mirror-gazing, and other fortunetelling games reaching a certain level of popularity. (As an aside, the first mention of apple bobbing in a literary text is apparently in a volume of Collectanea de Rebus Hibernicus, a book by Charles Vallancey chronicling the ancient history of Ireland--however I haven’t been able to find out which volume.)

With the emphasis on aesthetic, nature, folk art and customs, I think it would not be unwise to suggest a correlation between the rise of Romanticism in Europe (which hit its peak from about 1800-1850) and the development of Halloween into a more secular, “spooky” holiday of tricks, treats, and scares (which matures to the modern variation we are familiar with around 1900.)

Gothic (and Romantic) fiction so heavily draws on sources of the supernatural, occult, mythology, folklore, and religion, it would be unkind to say that the lore and ritual surrounding Halloween didn’t (or couldn’t) have a hand in shaping the genre. However, it’s incredibly rare to find a piece that could be considered Halloween literature—by which I mean literature that specifically touches, mentions, or takes place on Halloween. The earliest of works that qualify here are Irish and Scottish ballads and poetry--which alternate thematically from using the atmosphere of a ghoulish, spook-filled Halloween to inject a sense of nightmare or perhaps whimsy into the text, to fully embracing the changing of seasons and embracing of death in a sense of almost traditional homecoming.

Most notably, the earliest connection I’ve been able to find between Gothic fiction and Halloween is from a 1799 production of a play entitled, “Halloween; or, the Castles of Ahtlin and Dunbyane”. Produced by an Englishman named John Cross for the New Royal Circus in St. George’s Fields. It was a direct adaptation of Gothic heavyweight Ann Radcliffe’s The Castles of Athlin and Dunbayne from 1789; according to this source the play was “bookended […] with Halloween themes to add atmosphere and otherworldliness.” This author, Lesley Bannatyne, also suggests that Cross was capitalizing on the popularity of the then-recently published poem “Halloween” by Scottish Robert Burns—a poem which she argues gave a ‘face’ to Halloween in the 19th century, inspiring and influencing countless other works throughout and into the Victorian period. We also saw some more directly Gothic mentions of, or references to, Halloween in Joseph Sheridan Le Fanu’s “The Child That Went With The Fairies” (although today he is almost solely known for his vampire Gothic novella Carmilla) and poems like Edgar Allan Poe’s “Ulalume”.

I think it’s worth mentioning that Radcliffe had an extreme distaste for the supernatural in fiction—she took great lengths in rationalizing every supposed supernatural event; she always cared to unmask the ghosts and pull back the curtain. In a roundabout way, this very much pairs hand in hand with the whole concept of costumery and trick-or-treating of Halloween—where everyone is entitled to one good scare but it’s all smoke and mirrors.