“and you shall rejoice on your festivals” (Devarim 16,14)
It is a positive commandment to rejoice on the pilgrim festivals as it says “and you shall rejoice on your festivals”. The first topic that is hinted at in this rejoicing is that we should, at the very least, offer up a peace offering in the Beis Hamikdash. Furthermore, Chazal have said that one should rejoice in all different ways of rejoicing. This included eating meat and drinking wine, wearing new clothes and distributing fruits and different kinds of sweets to the young and to the women, playing musical instruments (applies) only in the Beis Hamikdash and that is termed the “Simchas Beis Hashoeva”.
Chazal have said that a person is obligated to make his children and the members of his household happy on the pilgrimage. How should he make them happy? Men in the way appropriate to them – with wine. Women in the way appropriate to them – with nice clothes. The Torah likewise warns us to make sure to include poor people, strangers and weak people in our joy.
Amongst the roots of the commandment: a person was created in such a way that his nature needs to rejoice sometimes just as he needs to eat and sleep continually. Hashem wants to merit us, for we are His people and the sheep of His flock, and He commanded us to perform this rejoicing in His name in order that we may merit before Him in all of our deeds. Hashem has fixed times in the year for us as festivals, to remember on them the miracles and good things which He has granted us, and He commanded us at those times to sustain our physical selves with the joy necessary for them. He has found for us a great medicine for when we are satiated with joy for the sake of His name and in His memory, this thought will provide us with a barrier which prevents us crossing too far over the line of propriety.
This commandment applies to the subject of rejoicing (but not to the subject of offerings) at every time and in every place to men and to women. One who does not rejoice, and make his household and poor people happy to the best of his ability for the sake of the commandment of the festival, has transgressed this positive commandment.