Hallow's Eve: A History

Hallow's Eve, or, more acurately, Samhain ("SOW-in"), is a pagan festival commemorating those who have died and passed on to the next world. During this fall Festival of the Dead, pagans, especially Wiccans and Druids, pay respects to the deceased and celebrate their new lives. As it is the last day of the year, the veil between the world of the living and the next is at its thinnest, allowing the spirits of the dead to return and visit their families. We light a candle (or a jack-o-lantern) and place it in a window to guide our ancestors and friends home.

There are those who believe that evil as well as good spririts can cross over at this time. This may have come from the Celtic practice of people playing pranks on their neighbors, such as stealing sheep or other farm animals. To ward off these tricksters and other negative presences, it is customary to light a bonfire and gather around it. This of course gave rise to all sorts of incorrect superstitions regarding pagans. For example, the fact that female Witches would use besoms (small, 4' long brooms) in ritual, combined with it being a phallic symbol, somehow led to the concept of hideous witches riding on broomsticks across the moon. In addition, arose the mis-informed association of the bonfire with orgy and Devil worship. These could not be further from the truth. Samhain was never associtated with evil or negativity.
Druids hold sacred ceremonies in which Ovates (the second step to becoming a Druid) conduct rites where they communicate with the dead. The world of the ancestors is one not of death but of transcendance, where the ancestors meditate for a time before being reborn and again entering the stream of life. That is why we should not mourn their death but celebrate their life.
Besides honoring the dead, Halloween is also a time for divining. Young people may divine their romantic future by use of apples, nuts, fires, or runes.

Samhain is the time we celebrate the new year. The Sun is at it's lowest, before the oncoming winter, and will (symbolically) die and be reborn in Midwinter, when it will melt the winter snows and reveal the spring. Personally, I attach this meaning to the bonfire, it being a symbol of the Sun's rebirth and continued protection. (Samhain is also the time for giving up that which you no longer need in life, and cleaning up your clutter.)

Consulted:
Witch Way. Check it out, it's great!
Halloween: The Pagan Festival of Samhain
Also worth checking out, Halloween Myths, Monsters and Devils, a site full of documents, commentary, and arguments regarding Pagan and Christian beliefs, as well as many links to others. Really a lot of hogwash. For a really good, objective outlook on Halloween and it's aspects, and history, check out Halloween, by Silver Ravenwolf.

Customs and Superstitions

Apples
Withes Besom
Divination and Scrying
Bonfire