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In a previous post we have seen that we have a mitzva (commandment) to rejoice on the festivals (the mitzva of simcha) and on the shabat (the mitzva of oneg). Now we will see in a bit more detail what it means to "rejoice" on a holiday.

First, let’s turn to the Talmud:

Our Rabbis taught: A man is in duty bound to make his children and his household rejoice on a Festival, for it is said, And thou shalt rejoice it, thy feast, [thou and thy son, and thy daughter, etc.] Wherewith does he make them rejoice? With wine. R. Judah said: Men with what is suitable for them, and women with, what is suitable for them. ‘Men with what is suitable for them’: with wine. And women with what? R. Joseph recited: in Babylonia, with coloured garments; in Eretz Yisrael, with ironed lined garments.
It was taught, R. Judah b. Bathyra said: When the temple was in existence there could be no rejoicing save with meat, as it is said, And thou shalt sacrifice peace-offerings, and shalt eat there; and thou shalt rejoice before the Lord thy God. But now that the Temple is no longer in existence, there is no rejoicing save with wine, as it is said, and wine that maketh glad the heart of man.
(Pesachim 109a, Soncino translation)

The proof passages that are cited are Psalms 104, 15 for wine and Deuteronomy 27:7 for meat. "Meat" in this context is clearly a reference to the temple sacrifice that was brought on the festival, the "korban shelamim". There does not seem to be an explanation for giving women clothes that I’m aware of.

The codification by Maimonides has a somewhat more exhaustive list of things that bring joy:

(Halacha 16)
It is forbidden to fast or recite eulogies on the seven days of Pesach, the eight days of Sukkot, and the other holidays. On these days, a person is obligated to be happy and in good spirits; he, his children, his wife, the members of his household, and all those who depend on him, as [Deuteronomy 16:14] states: “And you shall rejoice in your festivals.”

(Halacha 17)
What is implied? Children should be given roasted seeds, nuts, and sweets. For women, one should buy attractive clothes and jewelry according to one’s financial capacity. Men should eat meat and drink wine, for there is no happiness without partaking of meat, nor is there happiness without partaking of wine.
(Maimonides: Hilchot Yom Tov, 6:16-17)

Again, I am not aware of a textual basis for giving children sweets. There is a discussion amongst authorities if this list is the Rambam’s subjective list of things that generally bring happiness or if it is a set of objective guidelines that must be followed (Rabbi Josh Flug: The Mitzvah of Simchat Yom Tov).

So, bottom line, what do you "need" to do to rejoice? According to those who take the Rambam’s list to be objective guidelines, as a man drink wine and eat meat, give your wife clothes and your children sweets. According to some who view it as subjective, there might still be a rabbinic commandment to drink wine. And again, drinking wine might only be commanded if it makes you happy. In any case, even if you hold that you have to drink wine and/or eat meat but this does not make you happy, you are required to additionally do something that makes you personally joyful (whatever that something is) to fulfill the command!