3 times a year all Jewish males were required by the Lord to go up to Jerusalem.  These 3 times were on the Feast of Unleavened Bread, the Feast of Weeks of the firstfruits of the wheat harvest called Pentecost and the Feast of Ingathering also called the Feast of Tabernacles according to Exodus 23:14-17, 34:18-23, Leviticus 23:4-21,34-44, and Deuteronomy 16:1-17.  There is nothing in the Bible that I can find that required all the males to go up to Jerusalem on the Feast of New Wine or on the Feast of New Oil.

The Lord's requirement that all males go up to Jerusalem on the Feast of Weeks of the firstfruits of the wheat harvest is why Jews dwelling both in Jerusalem (Acts 2:5) and dwellers in other nations were in Jerusalem (Acts 2:9-11).

According to Acts 2:9-11, these Jews were Parthians, Medes, Elamites and dwellers in Mesopotamia, Judaea, Cappadocia in Pontus and Asia, Phyrygia, and Pamphylia in Egypt and in the parts of Libya about Cyrene and strangers of Rome, Jews and prosellytes, Cretes and Arabians.  All these Jews born in all these nations heard the Galilaeans speak in other tongues which they could understand because it was the language of the countries that these Jews in different nations were born in and dwelled in. This means those Jews who were dwellers in other nations had to make a required pilgrimage to Jerusalem.  So in my opinion it was at the Feast of Weeks of the firstfruits of the wheat harvest that the Holy Spirit descended on the 120 in the upper room.

According to Lev. 23:17-20 they were told to bring 2 wave loaves (of wheat) baked with leaven as firstfruits to the Lord which was to be offered with seven lambs without blemish of the 1st year, and one young bullock and 2 rams for a burnt offering unto the Lord, with their meat offering and their drink offerings, even an offering by fire, of sweet savour unto the Lord.  Then they were to sacrifice one kid of the goats  for a sin offering and 2 lambs of the first year for a sacrifice of peace offerings. And the priest shall wave them with the bread of the firstfruits for a wave offering before the Lord, with the two lambs.  In order to do this their offerings had to be presented to the priest at the temple in Jerusalem which is why the Jews dwelling in other nations (Acts were required by the Lord to go there.

Jesus had shown himself alive to his apostles for 40 days after his resurrection according to Acts 1:3 and told them they should not depart from Jerusalem (Acts 1:4-5) but to wait for the promise of the Father, which saith he, ye have heard of me.  For John truly baptized with water; but ye shall be baptized with the Holy Ghost not many days hence.  10 days later on Pentecost the Holy Spirit descended upon the apostles.  Otherwise they would have been waiting 60 days from the time Jesus told them not to depart from Jerusalem until the Feast of New Wine which would have been many days more to wait rather than not many which is another reason why I believe that the Holy Spirit did not descend on the apostles at the Feast of New Wine.