These are a shadow of the things to come, but the substance belongs to Messiah.
Sometimes we make the mistake of interpreting the Bible by the virtue of one verse instead of understanding the verse by the virtue of the overall context. That would be like saying that Yosemite Park is an orchard because of a couple of hazelnut trees (that I can document with pictures) in the middle of the vastness of the coniferous trees which define this beautiful expense of land.
When we read the verse, 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 (Colossians 2:16) in the mind-frame that God is telling us not to pay attention to His former command concerning the Levitical calendar and diet is doing just that. To read this with an anti-Torah observance twist is completely ignoring the context of the Letter to the Colossians.
This epistle was addressed to the formerly pagan Colossians striving to take Torah upon them while receiving criticism from others about it. Paul encourages them by telling them that they are right because, The Levitical calendar and diet concerns, are a shadow of the things to come, but the substance belongs to Messiah (Colossians 2:17). Every shadow betrays a shadow caster and in this case Messiah is the Shadow-Caster of the festivals and diet concerns in Leviticus.
Jewish sages have put together a Midrash that compares all of Jewish history to the phases of the moon. Here is how it works, ‘So all the generations from Abraham to David were fourteen generations, and from David to the deportation to Babylon fourteen generations, and from the deportation to Babylon to the Christ fourteen generations (Matthew 1:17). If each generation from Abraham is one day, we have a full moon at the time of king David, darkness at the time of the Babylonian deportation, indeed a dark time in our History, and a full moon again at the time of Messiah. Moonlight creates a shadow. If I were to stand still during the movement of the moon during the night I would see my shadow move from one place to the other, first behind me, then in front of me. In this case, Messiah is the shadow caster whose shadow we see on earth. We see His shadow both before and after His ‘full’ manifestation. Again, a shadow betrays a ‘Shadow-Caster’, and the diet and calendar Levitical injunctions are the ‘shadow’ of Messiah. Paul tells of those who would discourage the newly-born Colossian disciples’ attempts at following Torah that, they are ‘not holding fast to the Head, (Colossians 2:19; 1 Corinthians 11:13).
That same midrash needs another twenty-eight generations for the Messiah to return in His ‘fullness’. That gives us a time of darkness somewhere during the time of the Spanish Inquisition, again another dark time in our History, to take us again to the fullness of the manifestation of Messiah at the end of this age, when He comes to reign on the earth.
May it be soon Abba, even in our days. In the mean-time, may we rejoice in Him in the ‘shadow’ of His Presence among us.