There is a mitzvah to rejoice on all of the holidays, yet there is special emphasis on being joyful during Sukkot. As the Midrash1 notes, the Torah highlights the command to rejoice on Sukkot three times (as opposed to Shavuot, when we are commanded once, and Passover, when we are not explicitly commanded to rejoice).2

Furthermore, in our holiday prayers, each holiday is given its own descriptive name: Passover is the "Season of Our Liberation," Shavuot is the "Season of the Giving of Our Torah" and Sukkot is described simply as the "Season of Our Rejoicing!"

Why is Sukkot singled out?

Gathering the Produce From the Field

On the most basic level, the Torah itself gives the answer. We read: “You shall make yourself the festival of Sukkot for seven days, when you gather in [the produce] from your threshing floor and your wine pit. And you shall rejoice in your festival—you, and your son, and your daughter . . .”3 Apparently, this extra shot of joy is due to our stocked storehouses after the harvest.

Based on this, the Midrash4 explains why the Torah does not explicitly command us to rejoice on Passover, and only commands us one time regarding Sukkot. At Passover time, we are judged regarding the grain, but we don’t know yet what the crop will look like, since we only harvest it after Passover; on Shavuot we have gathered the grain and can now rejoice, but we didn’t yet gather the fruits from the trees so rejoicing is only mentioned once. But as the Midrash concludes, “On Sukkot, when the souls have received acquittal . . . and furthermore, we have already gathered not just the grain but the fruit as well, it mentions the imperative to rejoice three times.”

Look closely at the Midrash, and you’ll find that we’re not just happy because we have so much food in reserve—our souls have been acquitted. Viewed through this lens, the celebration of the harvest is much deeper than we originally thought.

Between Grain and Fruit

All that occurs in the natural order of the world is but a reflection of a deeper spiritual truth. Thus, by understanding the significance of the ingathering of the fruit, we can better understand the significance of the holiday of Sukkot.

The Rebbe teaches that we must first appreciate the difference between the gathering of the grain (which is celebrated by the holiday of Shavuot) and the ingathering of the fruit.5

For one, when it comes to grain, it doesn’t take that long—just a matter of weeks or months—from the time of planting until the crops ripen and you can enjoy the bounty. With fruit, however, it can sometimes take many years until you can finally enjoy the “fruits of your labor.” In addition, it takes much less labor to grow a stalk of wheat than it does to nurture a fruit tree to maturity.6

On the other hand, the amount of grain you harvest is commensurate with the number of seeds that were planted. A fruit tree, however, which was planted using a single seed, can produce an abundance of fruit for dozens of years. Thus, the fruit produced is incomparable to what was put into it.

Fruits From the Teshuvah Tree

The difference between grain and fruit can be compared to the difference between the divine service of the tzadik, the righteous individual, and that of the baal teshuvah, one who is repentant.

The righteous person travels on the straight and narrow path without too much concern or effort. Whenever he has a question of what to do, he turns to the Torah and follows it. He is therefore compared to grain, which can be harvested in a relatively short span of time with minimal effort.

The baal teshuvah, however, is compared to a fruit tree. It takes much effort and time, with many obstacles, twists and turns, to ultimately harvest the fruit. But it is precisely because of this that when he does finally harvest, he does so in abundance, and the yield is incomparable to the one single seed that was planted.

The divine service of the holidays of Passover and Shavuot is compared to the service of the righteous tzadik. He too celebrates, but it is with limitations, as whatever grows is only relative to what was planted.

However, shortly after the Giving of the Torah (on Shavuot), the Jews sinned with the Golden Calf, and it was not until the day of Yom Kippur that the Jews fully repented and G‑d forgave them for that sin. Thus, G‑d ordained that Yom Kippur be set aside as the Day of Atonement, a day dedicated to the Divine service of the baal teshuvah.

On Sukkot, which comes right after Yom Kippur, we celebrate the harvest of the baal teshuvah, which is compared to the fruit harvest. It takes lots of work, time and determination to get there, but the harvest of the delicious fruit is incomparable to what has been planted.

Thus, the Midrash tells us that we celebrate Sukkot because not only have “the souls received acquittal,” but we have gathered the fruits as well.

This is why the Torah uses the term “joy” three times. For according to Jewish law, when something is repeated three times, it is a chazakah, the halachic status of permanence. Thus, our job on Sukkot is to take this state of joy and happiness and carry it through the rest of the year!

For more on the Joy of Sukkot, as well as the joy of Simchat Beit Hashoeva, see here.