I found an interesting book online that had some Halloween historical references.
Halloween: From Pagan Ritual to Party Night by Nicholas Rogers is actually an Oxford University Press book, with footnotes and everything. There’s the obligatory first chapter about Samain, but then the second chapter points out that the history of All Saints sorta contradicts the idea that Halloween is pagan. (Okay, he says it in just one sentence that is easy to miss, but that’s better than most holiday history books.)
The main focus of the second chapter is how Hallowtide stuff was celebrated in England, before and after Henry VIII.
One interesting fact is that Hallowtide was a popular time for the Church to urge marriage, since Advent was coming up and you couldn’t get married in a fasting period like Advent.
Also, Hallowmas included a Gospel reading (possibly in the Office?) about the seven faithful virgins waiting for the Bridegroom to come and the wedding feast to begin. Rogers has a source that says a monks’ choir sang the antiphon about this with their hoods up, to look more like the girls waiting in the dark and cold. The online source didn’t include this footnote, but it sounds fun! Anyway, he points to this as the first move in the autumn and winter “masking season” of various fun parties and occasions for guising.
Before the Reformation, it was common to have prayer vigils on Halloween. These included the ringing of bells all night (which persisted even after it was outlawed by Edward VI), bonfires on hilltops, torchlight processions, praying for good fortune and good crops for the coming year and for the dead; as well as actual poor people going begging for food (so that they could eat better the next day, and throughout Hallowtide). (Shakespeare even talks about this in Two Gentlemen of Verona.) All Souls’ Day was the big cemetery visit day throughout most of Europe, and often involved eating a picnic or leaving food instead of flowers.
After the Reformation, customs splintered in England. In Catholic areas, there was still a lot of praying for the dead, fires, and candles throughout Hallowtide. (Up north, Catholic people would go out and pray for the dead in the middle of a field, in lieu of a church. One custom was to light a fire, and pray for the dead until it burned out.) In Protestant areas, sometimes the torchlight processions and other customs kept going, but it was sometimes about “scaring off witches” instead of encouraging prayer. “Souling” and giving out soulcakes was encouraged in Catholic areas, but “doling” tended to move to other November days in Protestant parts of England. (Guy Fawkes, St. Clement’s Day, St. Catherine’s Day, etc.)
Soothsaying on Halloween seems to have been connected originally with the marriage motif — part of games encouraging giggling, speculation, and courtship by the bashful. Girls would put rosemary under their pillows and hope to dream of their future sweethearts, or put nuts together in a fire in the name of a local couple, to see if the nuts would stay together or jump apart.
But with the transfer of praying for the dead to fearing witches and demons, there is an idea which emerges that you might be able to see visions or doppelgangers of those doomed to die in the next year. There was also divination by egg whites in water, in much the same fashion as reading tea leaves later on.
Less seriously, there were also lots of weather predictions based on Halloween weather.
On the benign side, since animals were slaughtered during Hallowtide (after the field harvest was over, and before you needed to worry about winter fodder), pig and cow bladders also became available for kids and young people to inflate and play with. And that’s why November is football season.
On the not so benign side, Hallowmas month was also the month of charivaris, grudge-settling, and pranks. People had time on their hands, it wasn’t winter yet, and it got dark early. Since it was a time of “misrule” fun leading up to Twelfth Night, and since there were lots of opportunities for wearing masks, you could get beat up, serenaded, or made to ride a rail by your exasperated or bullying neighbors.
Halloween in America, until somewhere in the 1950’s, was mostly about the romance and the pranks, with only a little bit of Scottish ghosties and ghoulies. Until trick or treating was made an activity for little kids, it often used to be much more about mild mischievous extortion than about doling or souling! So there’s a lot of applicable English material.
Highland Superstitions by Alexander Macgregor has a fair amount of Halloween material. It’s one of those read between the lines books, though. Why are young men running around the boundaries of their family farms at night, in the deiseil direction, with a “samhnag” torch? Is it a superstitious prehistoric magical ritual? Or is it a Scottish legal claim to land on the law-holiday of Samain? Is it the remnants of a really fast torchlight prayer procession, done to evade fines for practicing Catholicism? Or is it just a way to burn off energy and show athletic prowess? Who knows? He’s just reporting folkloric stuff in his time (in a disapproving way).
At any rate, the carrying of the torches was supposedly done to protect the farm from either crop failures and diseases, or the fairies. Then the samhnag torches, after being carried around the bounds, were supposed to be kept alight at the house, thus protecting pregnant women and babies on Halloween night from being stolen away.
Hallowe’en, much like May Eve, was one of the traditional nights when people could be stolen or returned. (Probably because traditional yearly work contracts started on the Celtic New Year, Samain, and ended on All Hallows’ Eve.) As I’ve pointed out elsewhere, Samain was the day when legal issues were settled by the local king and his assembly of nobles; and therefore the roads were more fully protected during the time before and after Samain, anybody could come see the king, and inter-kingdom travel was less of a legal problem. Even after Ireland and Scotland’s old legal system went away, supposedly the fairies still traveled on Samain and the way into their hills was left open.
There’s also a very sad story about why you shouldn’t play pranks on a poor girl throwing her blue clue into an unlit kiln.