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LITV says

Then do not let anyone judge you in eating, or in drinking, or in part of a feast, or of a new moon, or of sabbaths,

GW says clearly

weekly worship days.

for "Sabbath." However, WNT translates the last as:

or with regard to a festival, a new moon or a sabbath

(that implies there are two types of festivals, the pagan new moons and the Jewish festivals-Sabbaths). I have heard that while sabbath usually means the weekly worship day, it could also mean more generally as a day of rest, that includes all of the Jewish holidays. I heard that the Passover was regarded as a special sabbath somewhere.

So does this verse refer to special Jewish holidays or the weekly day of rest?

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    Pagan new moons? You do realize that the Jews observed Rosh Chodesh, i.e., the beginning of the month marked by the new moon, right? – user862 Mar 11 '15 at 2:25
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Scriptural context must be the primary driver for the answer, particularly because this section starts with "therefore". Paul's admonition to "let no one pass judgment" springs forth from verses 2:1-15. In 2:1-5, he desires to visit them "face-to-face" so that they may have a "...full assurance of understand and the knowledge of God's mystery, which is Christ..."...in whom are hidden all the treasures of wisdom and knowledge." Why? So "...that no one may delude [them] with plausible arguments." Paul was seeking to protect them from false teaching by helping them to understand, and have full knowledge of, Christ.

This then leads to V8, where he admonishes them to ensure they are not taken “…captive by philosophy and empty deceit, according to human tradition, according to the elemental spirits of the world, and not according to Christ.” This, I believe, is the key to this context: Paul juxtaposes Christ himself with philosophy and deceit that is according to “human tradition” and ungodly, worldly spirits. There are teachings being put forth that are fundamentally opposed to truth, to Christ.

Paul goes on to explain this by fleshing out who the Christ is and what the Colossians have in him. He is fully God in the flesh (V9) having all rule and authority (V10). They are filled in him (V9), not lacking in anything (from a righteousness perspective). Why? Because they were also circumcised in Jesus Christ (V11). To be as concise as possible, V11-15 are asserting that, because Jesus was cut off, or circumcised on their behalf, they are fully righteous, lacking in nothing in terms of their position / justification before God. By his becoming sin for them (2 Cor 5:21) and nailing their sin debt (taken into himself) on the cross (V14), taking on the curse of the Law for them (Gal 3:10-14), they have “...been made alive with [Jesus], having forgiven [them] all [their] trespasses.” This is the context of V16 and following.

Therefore, since they are filled up with Christ, being made once-for-all perfect (Hebrews 7:27), they need to add nothing to themselves in terms of righteousness, in law-keeping: their justification or standing before God. Why? Because in Jesus, they are already perfect as to the Law. In fact, Paul makes it clear in Galatians that those who are in Christ are in fact no longer under the law, it having been fulfilled in Christ’s obedience, and they are reckoned perfect in God’s sight having received Jesus’ perfect obedience as being credited to them. (See Romans 3-4 as well.)

So, being that this is the context, when Paul indicates that they should “…let no one pass judgment on [them] in questions of food and drink, or with regard to a festival or a new moon or a Sabbath”, he must be speaking to the fact that these things, regardless of their origin (Jewish holidays or official Sabbath days of rest), are no longer relevant to the Colossians in terms of their standing before God. These things no longer apply to them as needing to be done under the Law or as a command of God to please him. So, if they are not participating in these things, or if the elect to do so out of worship for God, they should no longer let others tell them they are judged before God for do or not doing so. Their standing before God does not depend upon these things, but upon what they already have in the Beloved.

In conclusion, to answer your question directly, I understand the historical context here to be that Jews, AKA “Judaizers”, were indicating to the church that at least some of the Old Covenant Law must be added onto Christ for them to be accepted by God, that they were still requirements for Christians that must be obeyed. This, however, in Paul’s (and therefore Christ’s) mind, completely antithetical to that which Christ had already accomplished in both his perfect life and substitutionary death. Here is a commentary that go into more depth.

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What is the meaning of Sabbaths in Colossians 2:16? First, the correct translation is the plural. Some translations have "Sabbath Day." Since Paul chose to use the plural, that is the right way to study it.

Leviticus 23 is a good place to begin a study on the Sabbaths. This chapter describes all of the appointed times. The most frequent is the weekly Sabbath. The annual calendar includes 7 days with restrictions against work: first day of Unleavened Bread, last day of Unleavened Bread, Feast of Weeks, Trumpets, Day of Atonement, first day of Tabernacles and the day following the seventh day of Tabernacles. Most people who follow the annual calendar would likely consider the annuals days of no work to be a Sabbath because of the restriction on working. In practice they become "Sabbaths." Also, since the annual calendar is supposed to be set by the months, it is possible that the weekly Sabbath would fall on an annual day.

In the strictest interpretation, only the Day of Atonement is described using the exact words as the weekly Sabbath:

Six days shall work be done: but the seventh day is the sabbath (sabbat) of rest (sabbatown), an holy convocation; ye shall do no work therein: it is the sabbath of the Lord in all your dwellings. (Leviticus 23:3 KJV)

It shall be unto you a sabbath (sabbat) of rest (sabbatown), and ye shall afflict your souls: in the ninth day of the month at even, from even unto even, shall ye celebrate your sabbath. (Leviticus 23:32 KJV)

The other days are simply days of rest (sabbatown). Strong's numbers are 7676 and 7677. The two words are similar yet different.

Sabbaths are not limited to 24-hour days:

But in the seventh year shall be a sabbath (sabbat) of rest (sabbatown) unto the land, a sabbath for the Lord: thou shalt neither sow thy field, nor prune thy vineyard. (Leviticus 25:4 KJV)

The same words used to describe the weekly Sabbath and the Day of Atonement are used to describe the Sabbath year.

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