Our Sages call all Jewish holidays “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 all. Moreover, 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 — something performed by all Jews. Thus, the additional measure of joy present during Sukkos is felt by even the humblest Jew.

Furthermore, during the time of the Beis HaMikdash , when the physical world enjoyed a greater degree of spiritual refinement, the greater degree of Sukkos joy permeated the physical world.

The festival of Sukkos is also known as Chag HaAsif , the “Festival of Ingathering,” for it also celebrates the gathering of the harvest. And during the time of the Beis HaMikdash , with “Every person under his grape arbor and fig tree,” the bountiful harvest caused a palpable joy.

That the world’s physical refinement enabled spirituality to take a more concrete form was indicated by the fact that physical offerings were brought when the Beis HaMikdash was standing, while nowadays prayer acts in their stead. Here too, the reason is that 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.

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 exists today. For the holiday of Sukkos follows close on the heels of the month of Elul and the awesome time of Rosh HaShanah, Yom Kippur, and the Ten Days of Penitence. 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 all of Sukkos is the “Season of our Rejoicing,” the emotion felt on the actual Yom Tov days of Sukkos is greater than that felt on Chol HaMoed , the intermediate days. This is readily understandable when one considers that the only labor permitted on Yom Tov is that which relates to the preparation of food for the day. Since the gratification is immediate, this hardly constitutes true labor , for the individual is instantly recompensed by pleasure.

This is not so with regard to the labor permitted during Chol HaMoed : during that period, all types of essential labor — Davar Ha’Avud — are permitted, even if gratification will only come 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 joy is once again heightened. Moreover, the joy attainable then is even greater than that attainable on Yom Tov itself. This is because the pleasure and delight obtained through labor permissible on Yom Tov is found on Shabbos as a matter of course — 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, and which acts as a stepping stone to Yom Tov’s joy and delight.

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