Halloween is one of my favorite holidays, which occasionally puts me at odds with others in the christian establishment.
For the most part, the people I hang out with the most now understand my enjoyment of the holiday and tend to feel at least somewhat similarly. However, once in a while I come across someone who is appalled that I actually really enjoy Halloween. 'It's the devils holiday.'
Actually, it isn't. At least not historically. Historically, it can be connected with a lot of pagan holidays, and a few of them did have death or the dead as its focus. However, the holiday most associated with Halloween is the Celtic festival of Samhain, which is primarily a festival for the end of harvest. Samhain did have some supernatural influences, but not as much to do with the 'day of the dead' as we have made it in modern times.
So then some may argue that 'it's still a pagan festival, we shouldn't celebrate it.' I don't disagree on the main point, that pagan festivals shouldn't be fully recognized, just as pagan gods shouldn't be worshiped. But our modern celebration of Christmas occurs in December, not because that's when Jesus was born (He was most likely born in Summer) but because the early church for some reason associated the birth of Christ with the pagan holiday of Saturnalia. The Christmas tree is from that background. The word Easter has nothing to do with Christianity, it is actually a an Old English/Germanic name for a long forgotten goddess and also the old name for the month we now call April. The egg hunts and the Easter Bunny all have their origin in non-Christian tradition.
It is posited that the early church adopted these dates and/or practices in order to more easily assimilate pagan cultures into Christianity as they converted. Whether you agree with that methodology or not, that is what has influenced the way we celebrate holidays in the modern world.
As for Halloween, Samhain became associated with All Hallows Eve, which is the night before All Saints Day (Nov. 1), the Catholic Church's recognition of all the saints.
I just like to put on crazy costumes and have some fun.