Let no man therefore judge you in food, or in drink, or in a holy day, or in the new moon, or in sabbath days: Which are a shadow of things to come; but the substance is of Christ. Col 2:16-17
Colossae was a Gentile city of some importance on the road that linked Ephesus on one end to the Euphrates Valley on the other end. It was Hellenized, or steeped in the culture of the Greeks, as was all of Asia Minor since its conquest by Alexander the Great some 300 years earlier. Paul’s instructions are directed to Gentile converts to belief in Jesus Christ. They were coming out of idolatry, and into the one biblical faith practiced by all believers in the Lord Jesus in Paul’s time: the worship of God in the Spirit, coupled with learning Moses in the synagogues (Act 15:21).
One aspect of discarding the practices of idolatry, and instead walking in a manner worthy of the Lord, walking in His ways according to the Scriptures (the Hebrew word “torah” simply means “teaching,” God’s teaching of His ways), was learning to celebrate His feast days rather than the pagan festivals, to honor His sabbath days rather than the holy days of the false gods, and receive their food with thanksgiving whether it was purchased in a meat market, or not (the “unclean food” issue of that day faced by the Gentile believers in the Lord Jesus Christ, living outside of Judea, see 1 Cor 8, clean and unclean food).
Let no man, Paul is saying, Jew or Greek, judge you in food or drink or holy days or new moons or sabbath days. They were learning a new way to live, prescribed by God’s word. They were growing and increasing in the knowledge of God. When they took their first tentative steps into sabbath rest, then, it is likely they did not understand all that the Torah and the Prophets had to say on the matter. They were babies learning to walk, and of course they would fall from time to time. On one side, there were some of the Jews who would judge them negatively for not being perfect in their holy day or sabbath day observance (the “torah police” who are still with us today, unfortunately). On the other side, there were their Gentile families, neighbors, and co- workers, who might judge them negatively for no longer participating in pagan celebrations or for abstaining from pork.
The holy days of the Lord, and new moons and sabbath days that the Colossians were now celebrating instead of pagan observances, are a shadow of things to come. The substance who casts the shadow, is the Lord Jesus Christ. The new moon has proclaimed Messiah prophetically since Creation. The sabbath has proclaimed Messiah prophetically since Creation. The holy days of the Lord have proclaimed Messiah prophetically since Moses, and do so even today.
Food and drink, holy days, new moons, and sabbath day observance has not passed away (Mat 5:17-19). However, they are the shadow, not the substance. The Colossians had received Christ Jesus the Lord (vs. 6) and had therefore received the substance. He was their confidence before both Jews and Greeks, and why they could hold their head up before the torah police on one side, and the pagan idolaters on the other.