I have a screen shot on my tablet captured from another watcher describing what is to happen on the Feast of New Wine relative to the Feast of New Grain (winter planted wheat).  I believe this Feast of New Wine is actually the timing of the true Pentecost.

Here is the description:

Instruction from the Temple Scroll of the Dead Sea Scolls.

You shall count beginning from the day when you bring the new grain offering to the LORD, the bread of the firstfruits, seven weeks, seven full weeks, until the day after the seventh Sabbath,  You are to count fifty days, then sacrifice new wine as a drink offering . . . then the whole people, great and small, may begin to drink the new wine and to eat grapes from the vines, for on this day they will make atonement for the wine.  So the children of Israel are to rejoice before the LORD, this being an eternal statute, generation after generation, wherever they may dwell.  They shall rejoice this day in the festival of new wine to pour out a fermented drink offering, new wine upon the altar of the LORD, as an annual rite. . . . [the priest]s shall drink first and the Levites [second] . . . the princes of the standards first . . . [men of] renown.  After them the whole people, from the great to the small, shall begin to drink the new wine.  The shall not eat any unripe grapes from the vines, for on this day they shall expiate for the tirosh.  The children of Israel shall rejoice before YHWH, an eternal rule for their generations wherever they dwell.  They shall rejoice this day for they have begun to pour out an intoxicating drink offering, the new wine, on the altar of YHWH, year by year.

Now, compare the above with what Paul expresses in II Timothy 4:6-8:

6For I am already being poured out as a drink offering, and the time of my departure has come. 7I have fought the good fight, I have finished the course, I have kept the faith; 8in the future there is reserved for me the crown of righteousness, which the Lord, the righteous Judge, will award to me on that day; and not only to me, but also to all who have loved His appearing.

Perhaps Paul knew timing after all, just not the year.

Perhaps this is why Paul cut one of his missionary journeys short so as to get back to Jerusalem by Pentecost per Acts 20:16:

For Paul had decided to sail past Ephesus so that he would not have to lose time in Asia; for he was hurrying, if it might be possible for him to be in Jerusalem the day of Pentecost.