A few months back I was trying to explain to my children why I hate Halloween. While I did not want to get into the history of the whole idolatry thing, I was able to explain that it was just not our custom. They thought I said costume, and objected. “But Abba, you love costumes on Purim”. That is true. I do love Purim. Then I got to thinking, why do I love Purim and hate Halloween?
While we dress up in costumes and we give our treats on both days, Purim is just a better holiday. While on Halloween the person wanting the treat needs to go around the neighborhood collecting said treats, on Purim the obligation of traveling around is on the giver and not receiver of the treats. It is not that you spend any more or less money on treats on either day, it is just that Purim has better “costumer service”. –Chag Purim Sameakh
Somehow Halloween smacks of entitlement. Purim, not so much.