Halloween is a very touchy subject within the church. "What should we do? Do we boycott it?" There is no doubt that Halloween's origins can be traced to pagan beliefs and rituals, or that some Satanic groups see it as a special holiday. Many Christians differ on their views of whether or not believers should have any participation in Halloween celebrations, because they see it as potentially dangerous from a spiritual perspective. Christians certainly should not participate in the "dark side" of Halloween, approve of the Satanic, or the focus on paganism and evil.
The reality of Halloween participation for believers and unbelievers alike is that of dressing up in costumes and having fun trick-or-treating around the neighborhood. To many, this is all of what Halloween is about, without any connection to occult or pagan practices. As a comparison, from a Christian standpoint, Christmas is a celebration of the birth of Christ and the beginning of His life on earth. Would we naively say that ALL people celebrating Christmas are Christians rejoicing at the birth of Christ? Not at all! The same goes for Halloween—not EVERYONE participating in Halloween events are rejoicing over pagan rituals.
The difference is in the heart of the people that are celebrating. When I have children, I plan to let them go trick-or-treating, but I will have explained my convictions to them in ways they will understand to make sure they have the right heart. I don't mean to be dogmatic on this topic as I know people's convictions are different, but I will say that we should do all things properly in the eyes of the Lord, providing insight and truth when the question comes up. Whatever conviction you hold about participating in Halloween, live it out for God’s glory!