Romans 14:5-6a
One person esteems one day above another; another esteems every day alike. Let each be fully convinced in his own mind. 6 He who observes the day, observes it to the Lord; and he who does not observe the day, to the Lord he does not observe it.
There was little context for this verse provided, but when referring to the mind in that verse, I don't think it's a decision we make by supporting it with worldly reason, such as has been intimated in this thread, see:
Romans 12:1-2 said:
I appeal to you therefore, brothers, by the mercies of God, to present your bodies as a living sacrifice, holy and acceptable to God, which is your spiritual worship. 2 Do not be conformed to this world, but be transformed by the renewal of your mind, that by testing you may discern what is the will of God, what is good and acceptable and perfect.
This part of Romans seems to be more about judging others and not about what is right or wrong, in fact, right before Romans 14:5, Paul writes:
Romans 14:4 said:
Who are you to pass judgment on the servant of another? It is before his own master that he stands or falls. And he will be upheld, for the Lord is able to make him stand.
Also, the context of the days under question doesn't seem to align strongly with this topic. I read the topic as not about a specific day, but about a specific celebration. October 31st is just another day, what we do on/with that day is what matters. And frankly that's what I think the verse is talking about. It's not giving license to celebrate anything one wants, its giving license to live/give any day to the Lord.
Even if Romans 14 was giving such license, we should also consider 1 Corinthians, and understand that by choosing to do such when brothers in Christ may be discouraged or encouraged to stumble may indeed be sin.
1 Corinthians 8:9-13 said:
But take care that this right of yours does not somehow become a stumbling block to the weak. 10 For if anyone sees you who have knowledge eating in an idol's temple, will he not be encouraged, if his conscience is weak, to eat food offered to idols? 11 And so by your knowledge this weak person is destroyed, the brother for whom Christ died. 12 Thus, sinning against your brothers and wounding their conscience when it is weak, you sin against Christ. 13 Therefore, if food makes my brother stumble, I will never eat meat, lest I make my brother stumble.
As several have hinted, some of the activities in some holidays might fall short of the litmus test in Philippians:
Philippians 4:8 said:
Finally, brothers, whatever is true, whatever is honorable, whatever is just, whatever is pure, whatever is lovely, whatever is commendable, if there is any excellence, if there is anything worthy of praise, think about these things.
In the end, we should understand that guidance comes from the Lord and just because we want to do something, or see value in it, doesn't make it right. Wisdom only comes from Him.
Proverbs 3:5-8 said:
5 Trust in the Lord with all your heart,
and do not lean on your own understanding.
6 In all your ways acknowledge him,
and he will make straight your paths.
7 Be not wise in your own eyes;
fear the Lord, and turn away from evil.
8 It will be healing to your flesh
and refreshment to your bones.
I cannot recall a single place in His word that exalts evil, or diminishes it, in the way that Halloween does. It matters what the roots are, but it matters more what it is.
I know that some of my brothers and sisters in Christ struggle with what this holiday does and what it means more so than any other holiday. Therefore, if Halloween makes my brother stumble, I will never celebrate Halloween, let I make my brother stumble. Whatever perceived benefits that Halloween provides, I trust that the Lord will provide greater in its absence.
For the record, I also don't celebrate Easter, at least not the bunny and eggs version.