Our Sages designate all Jewish holidays as “Festivals for Rejoicing.”1 Nevertheless, Sukkos is the only festival designated as “The Season of Our Rejoicing.”2

We thus understand that there are different degrees of joy, and that the joy of Sukkos — “The Season of Our Rejoicing” — possesses the greatest degree of joy of all. Moreover, the manifestation of the joy that accompanies Sukkos is a revealed and palpable dimension of joy.

This may be seen from the fact that the term “Season of Our Rejoicing” was established by the Rabbis to be part of our holiday prayers — prayers recited by all the Jewish people. Thus, the additional measure of joy present during Sukkos is felt by even the humblest Jew.

Moreover, during the time of the Beis HaMikdash, when the physical world enjoyed a greater degree of spiritual refinement and Divine revelation, the greater degree of Sukkos joy permeated not only the Jew, but the physical world as well.

The festival of Sukkos is also known as Chag HaAsif, the “Festival of Ingathering,” as it also celebrates the gathering of the harvest. During the time of the Beis HaMikdash, when “every person wasunder his grape arbor and fig tree,3 ” the bountiful harvest caused a palpable and revealed degree of joy to be felt within the world.

That the world’s physical refinement enables spirituality to take a more concrete form, is also indicated by the fact that physical offerings were brought when the Beis HaMikdash was standing, while nowadays prayermust take the place of offerings:

During times of exile, the physical world is less refined, so we cannot serve G‑d by bringing physical offerings, for the physical is now too coarse to serve as an offering. Prayer, however, as it consists of a wholly spiritual experience, can be offered during the time of exile.

Although the joy of reaping the harvest experienced on Sukkos existed in its physical sense only during the times of the Beis HaMikdash, the spiritual aspect of reaping the harvest also exists today.

For the holiday of Sukkos follows close on the heels of the month of Elul and the awesome days of Rosh HaShanah, the Ten Days of Repentance and Yom Kippur. The Jew’s service during this most important period in the Jewish calendar results in a bountiful spiritual harvest during the festival of Sukkos.

Although the “Season of Our Rejoicing” encompasses all of Sukkos, the joy felt on its actual Yom Tov days is greater than that felt on Chol HaMoed, the intermediate days. This is readily understandable when one considers that the only form of labor permitted on Yom Tov is labor that directly relates to the preparation of food for the day. Since the gratification of this labor is immediate, this hardly constitutes true labor for the individual is instantly recompensed with pleasure.

This is not so with regard to the labor permitted during Chol HaMoed: during the intermediate period of Chol HaMoed, all types of essential labor — davar ha’avud— are permitted, even if the gratification for this labor will only come about in the distant future.

Thus, during Chol HaMoed, the individual cannot possibly be as joyous as on Yom Tov, for his preoccupation with toil keeps him from fully enjoying the festival.

But this is only true of the weekdays of Chol HaMoed. When Shabbos Chol HaMoed comes, all labor is prohibited — even that which is permitted on Yom Tov — and the individual’s joy is once again increased.

Moreover, the joy that one can attain on Shabbos Chol HaMoed is even greater than the joy that is attainable on Yom Tov itself. This is because the pleasure and delight obtained through labor permissible on Yom Tov is automatically manifeston Shabbos — on Shabbos “All of one’s labor has been completed.” Additionally, Shabbos delight is engendered without any need for labor, while Yom Tov needs the labor that precedes it, acting as it does as a stepping stone to Yom Tov’s joy and delight.

Based on Likkutei Sichos, Vol. XIV, pp. 418-420.