Colossians 2:16 Let no man therefore judge you in meat, or in drink, or in respect of an holyday, or of the new moon, or of the sabbath days:
17 Which are a shadow of things to come; but the body is of Christ.
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Romans 14:4 Who art thou that judgest another man's servant? to his own master he standeth or falleth. Yea, he shall be holden up: for God is able to make him stand.
5 One man esteemeth one day above another: another esteemeth every day alike. Let every man be fully persuaded in his own mind.
6 He that regardeth the day, regardeth it unto the Lord; and he that regardeth not the day, to the Lord he doth not regard it. He that eateth, eateth to the Lord, for he giveth God thanks; and he that eateth not, to the Lord he eateth not, and giveth God thanks.
Agreed, but you're reading a lot into here. First off, holy days ARE, not were, ARE a shadow of things to come. Certainly that's true. The sabbath (a holy day) portends the millenial rule of Christ. The Feast of Trumpets portends, is a shadow of, the return of the King, Jesus Christ, to earth.
The context of Collosians 2 is not letting anyone judge you in HOW you are keeping the holy days, not whether or not you are keeping them. If you do a word study on "meat" and "drink" you'll see that they are more properly translated as "eating and drinking". They (the members of the Colossians church who were keeping the holy days of God) were being criticized for celebrating the holy days in too celebatory of a manner.
5 One man esteemeth one day above another: another esteemeth every day alike. Let every man be fully persuaded in his own mind.
6 He that regardeth the day, regardeth it unto the Lord; and he that regardeth not the day, to the Lord he doth not regard it. He that eateth, eateth to the Lord, for he giveth God thanks; and he that eateth not, to the Lord he eateth not, and giveth God thanks.
I know you're an honest person when it comes to scripture research Quester. Compare the greek for "holy day" in Colossians 2:16. Do a Strongs search and see that when that word is used it always refers to the holy days God created.
Then compare Romans 14. The term for "holy day" is never used. Then read all of Romans 14. If you're honest, you have to come away with the impression that Chapter 14 is focused exclusively on eating and drinking practices. Practically every other verse mentions eating or drinking, including verse 6, the one you cited. The "days" referred to are days associated with eating and drining. They could be pagan days where animals were sacrificed and the meat later sold in markets, or it could be referring to fast days instituted by the Pharisees (Luke 18:12).
Either way it's highly unlikely that it's referring to God's Holy Days. Their "bible" at the time was what we call the old testament. There's no way it could have been understand to mean what you're suggesting without causing a huge controversy in the church.