Why do I consider Halloween a “little Easter”? Several reasons:
1) Liturgically – Halloween (“All Hallows Eve”) is the first day of the sacred triduum (three days) of the Fall. It’s followed by All Saints’ Day on November 1st and All Souls’ Day on November 2nd. This forms a nice balance to the sacred triduum of the Spring – Holy Thursday, Good Friday and the Easter Vigil Mass celebrated on the night of Holy Saturday.
2)Thematically – Just as the Easter triduum is a celebration of life over death so is the sacred three days of the Fall. Taken together, they invite us to celebrate and meditate upon the mystery of the Communion of Saints – that wonderful proclamation rooted in the Resurrection that Death only separates us from the ones we love in the flesh. In the spirit – and one day in the glorified body – we are actually closer to those we love than we ever were when they walked with us on this earthly pilgrimage. (Spend a few quiet moments with this mystery today.)
3) Culturally – On Halloween we dress up our kids in spooky costumes and our homes in spooky decorations all in the spirit of fun. It’s as if we all get together, children and their parents, young and old, neighbor with neighbor to look Death right in the eye and say, “We know you are only an imposter. And we are not afraid of you.” All against the background of the blaze of glory that nature provides reminding us that however cold and dark Winter might be, it isn’t the final word.
To those who think that Halloween represents the downward spiral of a Catholic custom into paganism, I would ask that you conisder this: If we began to pull everything out of our rich and varied Catholic faith that smacked of paganism, we wouldn’t have much left. Time and again the Church has sought out what is most meaningful and beautiful in the cultures it has encountered – much of which we would classify as paganism – and through the guidance of the Holy Spirit baptized and purified it so that it might reflect the gospel. (Do some reading on Christmas celebrations, for example.)
Jim Philipps (3rd millenniumpilgrim)
3rdmillenniumpilgrim's Blog 
I’d like to add to this interesting post mention of the wonderful tradition from Mexico, Dia de los Muertos when families prepare lots of food, often the favorite dishes of the departed, and visit the graves of loved ones. Although I’ve never experienced this ritual first hand, I imagine it is rather more festive than somber. It seems to represent a continuing connection with those who have died and keeps them part of the family! As it should be, I’d say.
In our parish a Lazarus mass is celebrated the night of All Souls. We remember all those in the parish and in the wider community who have died within the past year. I’ve attended a few times and found it a moving and healing service. It provides a way to honor and commemorate those we have lost in the flesh.
In my own experience, I’ve marked four years this October since my dear friend Robert has died. During this time, I feel I have come to understand him better than I ever did during his lifetime. And that makes me continue to feel close to him, this season of the bright flaming colors of the spirit.