Therefore let no one pass judgment on you in questions of food and drink, or with regard to a festival or a new moon or a Sabbath.  These are a shadow of the things to come, but the substance belongs to Christ.
There is a sense in which grace will always clash with human nature.
The reason being that grace undermines our efforts to justify ourselves. It runs counter to human pride that draws us to boast in our accomplishments. It clashes with self reliance and one’s own ability to make things happen.
Grace pushes everything away from us and points to God. Grace undermines our best efforts at establishing a list of requirements and prohibitions that we can impose on ourselves and on others as the condition by which we gain acceptance with God. Grace demands only one thing: that all glory and honour and credit be given to Jesus Christ for what he has done, not for what we have done and human nature instinctively struggles with that.
That is why, wherever the ‘of grace’ is preached, legalism fights back.
Once you declare that God has graciously provided everything we need in the person and work of Jesus Christ you can rest assured that fallen human nature will rise up in protest and try to sneak in somewhere a rule or regulation that we, in our strength, can fulfil, or an observance or ritual that we, without God’s enabling power, can perform that will enhance our spiritual standing and in some way impress God.
The Colossians had heard and received, by grace, the gospel of grace. They had turned from self-reliance and self-justification to rest wholly in the all-sufficiency of what God had done for them in Jesus Christ alone. But there were some folk in Colossae, as there are similar folk everywhere in our day, who struggle with grace and need to add on a few laws here and there. We know what they were up to because of Paul’s passionate and very pointed words “Don’t let them judge you!” (vs 16).
We can see from Paul’s words that the problem was varied and complicated however, Paul does focus on two things in particular.
Firstly those preachers of religious laws who were insisting that the Colossians abstain from certain food and drink. This is probably not a reference to Old Testament dietary regulations, because the Mosaic Law contained no significant prohibitions concerning what a person drank (there were a few exceptions, of course, as in the case of those who took a Nazarite vow).
These people were probably demanding abstinence from meat and strong wine as a demonstration of faith. They were convinced that abstinence was inherently more pleasing to God than participation. In other words, like some today, they believed that self-denial was intrinsically more spiritual or an indication of a greater passion for God. The self-discipline required to say ‘No’ to the offer of something to eat or drink was thought to be a mark of genuine piety and commitment to God.
I don’t know, but maybe they feared that by the eating of certain foods and that drinking certain drinks would affect deeply their relationship with God. They might have believed that partaking would diminish their religious fervour and perhaps expose them to things like “temptation”. Nowhere is this perspective endorsed in the New Testament. It is true, of course, that those who drink and eat to excess are biblically rebuked (drunkenness and gluttony).
Evidently these false teachers in Colossae were declaring that those who enjoyed their freedom in Christ to eat and drink within the parameters established in Scripture stood condemned or were close to Divine judgement. “No,” said Paul. “Don’t let them judge you!”
Secondly, Paul challenges the legalism surrounding the “festival” and “new moon” and “Sabbath.” This may have come from some devoted Jews at Colossae as they are a reference to the holy days of the Jewish calendar (specifically, the annual, monthly, and weekly observances). This very language is used often in the Old Testament to describe the sacred times found in the Mosaic covenant. (See 1 Chronicles 23:31, 2 Chronicles 2:4 and 31:3)
These observances, says Paul, were but a “shadow of the things to come” (vs 17). The “things to come,” is not a reference to what is future to Paul, but what was future to those who lived at the time when the obligation to abide by these holy days was in force.
During the time of the Mosaic covenant they had their place and fulfilled a glorious divine purpose. But that purpose was to point to Christ! They were a shadow of a greater and more substantive reality that is now present in its fullness in Jesus Christ and all that we have in him.
That is why Paul exhorts the Colossians (and us) not to let anyone suggest they are sub-Christian if they choose not to celebrate these festivals or observe the regulations associated with them during the time of the old covenant. Everything they symbolised, everything they foreshadowed, everything they were designed to teach and accomplish has now come to full and final fruition in Jesus!
Is a Christian free to abstain from certain foods and drink? Yes, so long as you do not impose your choice on others or suggest that they have fallen short of what is acceptable to God.
Is a Christian free to observe those religious holy days mentioned in the passage? Yes, as long as they do not think that God now regards them as more holy or more committed or more acceptable than those who do not observe them. However, we now have, in Christ, everything and more than those days were designed to provide so why would you want to observe them? In fact we have to be careful because by placing an importance on such days we come perilously close to denying that the fulfilment that is in Christ is enough. Why live with the shadows when Christ is in clear view.
So Paul’s counsel is to be very wary of legalists and legalism. Beware those who pass judgment on spiritual worthiness based on practices and observance that God does not require. What his grace has provided for us in Christ is enough. Period. Full stop. End of!