Many holidays (including Halloween, Thanksgiving, Christmas, Easter and others) are pagan in origin and involved the worship of false gods and idols. The Roman Catholic Church took many pagan holidays and “Christianized” them, so that the new converted pagans could still celebrate them.
YHWH has His own holy days (the sabbath and Leviticus 23 feasts). Also, there are other Jewish days to remember such as Hanukkah. There are plenty of holidays we can participate in and celebrate.
For me it isn’t a “legalism” issue, and we are no longer bound by the law as Yahushua fulfills the law. The law does not save, and attempting to keep the law for a means of salvation only brings condemnation. We are saved by His grace alone not by works. Yahushua is the way, the truth, and the life.
The law teaches us what is right and wrong in YHWH’s eyes. It teaches us what pleases and displeases Him. The law leads us to Yahushua, and He kept the law during His life on Earth. Yahushua celebrated Abba’s dedicated days. I want to be dedicated to YHWH and Yahushua alone. I love Abba and my Adonai more than anything else, and I do not want to take part in the ways of this world.
We walk in Christian liberty, not legalism. So after prayer and consideration, do what you believe is right. While imperfect… as for me, I will serve YHWH and reject as much of this world as possible.
“Do not love the world or the things in the world. If anyone loves the world, the love of the Father is not in him” (1 John 2:15).
“Adulterers and adulteresses! Do you not know that friendship with the world is enmity with God? Whoever therefore wants to be a friend of the world makes himself an enemy of God” (James 4:4).
I could go into great detail concerning the holidays and all, but there are plenty of resources on the internet to find the information. As to YHWH’s view on the matter see Deuteronomy 12:28-32.