My best Halloween memory would have to be the year I was 12 and went trick-or-treating for the last time.
I had always just gone with my brother and parents in a small subdivision near our home. This year we were invited to go along with a couple friends a few neighborhoods away, the kind of old family friends whom we had known since birth. But also the sort who, as we grew older, we didn't have as much in common with. We didn't get together to "play" anymore and we all quietly understood we would always share loyalty and fond memories, but without necessarily being present day parts of each others' lives. Not tonight though! The parents all passed out candy and sent us kids off in a group by ourselves to collect candy. We made the most of it!
It was all 100% innocent - no mischief, no breaking rules or TPing houses, and nothing sinister or mysterious happened. We simply ran from house to house in the cool, dark night (the kind that makes for an absolutely perfect October 31st). I recall thinking at one point that it felt like flying. Just crisp air and freedom. The perfect combination of childhood fun and the hint of independence I was growing into.
I realize it sounds simple and standard, but to me it cemented a love for what Halloween could be: a melting pot (cauldron?) of old and new, light and dark, innocent fun and adult exploration. A goodbye to something old and familiar, but the start of a new season full of potential.