When I was a kid Halloween was one of my favorite holidays. It was the first time that as kids my brother and I were given more freedom. We lived in trailer parks as kids, so the neighborhood was pretty confined, so it wasn't like we were going to be able to hike miles from home. It was the first night that we were pretty much able to go out on our own, with just our friends and go trick or treating. There were probably about two hundred or more trailers in the park and I bet we hit every one. Maybe twice.
It was that taste of freedom, that first taste of being a grown up at the age of ten or so, being trusted enough to go out on our own. Nowdays kids spend the night out on their own at that age, back than it was a little different. We would march from trailer to trailer, collecting as much candy as we could. Than coming home we would dump our backs on the living room floor and check our loot out. There was always more candy than we were ever going to eat, though try as hard as we could to eat it all we would.
To me Halloween will never be the costume parties as we got older, that rolling people's houses, whatever grown up fun we attempt on this night. It'll always be that venturing out in the darkness with just me and my brother, with no grown ups, being able to go where we wanted. (Ok, I know it wasn't quite that much freedom, we were limited to the trailer park and we had to be home before it was too late, but to us it felt like real freedom.) To me Halloween will always mean freedom.