According to the opinion in the Talmud (Sukkah 11b) that Sukkos is a commemoration of the ענני הכבוד, the Clouds of Glory, it is understandable why the Torah wishes to commemorate such a spectacular miracle. But according to the opinion that it is to commemorate the actual sukkos (some sort of temporary dwelling or tent) that our ancestors erected in the desert, why should this be commemorated?
If we were “rationalists”, we would be very happy with this commandment as a simple historical commemoration, in the style of a Civil War re-enactment (to the extent that rationalists believe in the Desert Sojourn), and maintain that we prefer to follow the rational opinion in the Talmud. Or even better, we would make up our own rational explanations.
But as Torah Jews, we must find a better explanation:
The Ramban on Emor writes as follows:
כי בסכות הושבתי את בני ישראל ענני כבוד לשון רש"י (רש"י על ויקרא כ״ג:מ״ג) והוא הנכון בעיני על דרך הפשט כי צוה שידעו הדורות את כל מעשי ה' הגדול אשר עשה עמהם להפליא ששכן אותם בענני כבודו כסוכה כענין שנאמר (ישעיה ד ה ו) וברא ה' על כל מכון הר ציון ועל מקראיה ענן יומם ועשן ונגה אש להבה לילה כי על כל כבוד חפה וסוכה תהיה לצל יומם מחרב וגו' ומפני שכבר פירש שענן ה' עליהם יומם ועמוד האש בלילה אמר סתם כי בסכות הושבתי שעשיתי להם ענני כבודי סכות להגן עליהם והנה צוה בתחילת ימות החמה בזכרון יציאת מצרים בחדשו ובמועדו וצוה בזכרון הנס הקיים הנעשה להם כל ימי עמידתם במדבר בתחלת ימות הגשמים ועל דעת האומר סכות ממש עשו להם (סוכה יא) החלו לעשותן בתחילת החרף מפני הקור כמנהג המחנות ולכן צוה בהן בזמן הזה והזכרון שידעו ויזכרו שהיו במדבר לא באו בבית ועיר מושב לא מצאו ארבעים שנה והשם היה עמהם לא חסרו דבר:
THAT I MADE THE CHILDREN OF ISRAEL TO ABIDE IN BOOTHS. “This means the clouds of Glory” [which surrounded the camp of the Israelites during their stay in the wilderness]. This is Rashi’s language. And in my opinion this is the correct interpretation [even] according to the literal sense of Scripture, for He commanded that the generations should know all the great deeds of the Eternal which He did wondrously with them, that He made them dwell in the clouds of His Glory like in a booth, similar to what is said, And the Eternal will create over the whole habitation of Mount Zion, and over her assemblies, a cloud and smoke by day, and the shining of a flaming fire by night; for over all the glory shall be a canopy. And there shall be a ‘succah’ (pavilion) for a shadow in the day-time from the heat etc. And since Scripture has already explained that the cloud of the Eternal was upon them by day and the pillar of fire by night, He just says here, that I made the children of Israel to abide in booths, [without explaining what kind of booths, but meaning] “I made them booths out of the clouds of My Glory to protect them.” Thus He commanded that at the beginning of the summer season we are to remember the exodus from Egypt by [calling] its month [the first of the months], and by observing its festival [of Passover], and He further commanded the remembrance of the continuous miracle which was done for them throughout the days of their stay in the wilderness, at the beginning of the winter season.
And according to the opinion of the Sage who says that they made themselves booths in the literal sense, [we must explain that the reason why this commandment is to be observed at the onset of the winter season], is because they began to make them at the beginning of the winter, on account of the cold, as is customary in camps, and therefore He commanded [that we also make] them at that time. The sense of the remembrance is that they should know and remember that they were in the wilderness, and did not live in homes, and they found no city of habitation for forty years, but G-d was with them and they lacked nothing.
That is, we have Pesach, which is a commemoration of the actual Yetzias Mitzrayim, and we have Sukkos, which is a commemoration of how Hashem sustained and protected us during the entire sojourn in the desert. Pesach is about the one-time event in which Hashem released us from slavery and raised our status from the dung-heap to the pinnacle of the world, Sukkos is about His constant sustenance and protection.
Perhaps this explains why Sukkos is the holiday with the greatest rejoicing, as the Rambam states (Shofar, Sukkah, Lulav 8:12). Hashem’s continual sustenance and protection, his Hashgacha1, is something we experience on a daily basis, and doesn’t require a deep spiritual awareness to appreciate, but is close to our consciousness. This would have been especially true in agricultural societies, when Sukkos was the time of gathering, but is something we can still appreciate today when plenty abounds. It is therefore very easy to feel acute happiness about this concrete manifestation of Hashem in our world.
However, despite the joy we may feel about physical matters, the primary happiness should be about spiritual affairs, service of Hashem, coming close to Him, and cleaving to His Torah. As the Magid Mishneh writes at the end of Hilchos Sukkah and Lulav:
ועיקר הדבר הוא שאין ראוי לו לאדם לעשות המצות מצד שהן חובה עליו והוא מוכרח ואנוס בעשייתן אלא חייב לעשותן והוא שמח בעשייתן ויעשה הטוב מצד שהוא טוב ויבחר באמת מצד שהוא אמת ויקל בעיניו טרחן ויבין כי לכך נוצר לשמש את קונו וכשהוא עושה מה שנברא בשבילו ישמח ויגיל לפי ששמחת שאר דברים תלוים בדברים בטלים שאינן קיימים אבל השמחה בעשיית המצות ובלמידת התורה והחכמה היא השמחה האמיתית.
The main idea is that a person should not perform mitzvos from a sense of obligation and compulsion, but should perform them out of joy. He should do the good because it is good and choose the truth because it is the truth, and the effort should feel effortless to him, and he should understand that this is what he was created for, to serve his Creator. And when he fulfills the purpose of his creation, he he will rejoice, for the happiness of earthly matters depends on worthless things that do not last, but the happiness of mitzvos, learning Torah and wisdom is the true happiness.
And it is through the extra rejoicing on Sukkos that we can learn this lesson and apply it to the entire Torah, the entire year.
The connection between Hashem’s hashgacha throughout the desert sojourn and His constant hashgacha in our lives is most clearly stated in Rashi (Shemos 16:32):
לדרתיכם. בִּימֵי יִרְמְיָהוּ; כְּשֶׁהָיָה יִרְמְיָהוּ מוֹכִיחָם לָמָּה אֵין אַתֶּם עוֹסְקִים בַּתּוֹרָה? וְהֵם אוֹמְרִים נַנִּיחַ מְלַאכְתֵּנוּ וְנַעֲסֹק בַּתּוֹרָה, מֵהֵיכָן נִתְפַּרְנֵס? הוֹצִיא לָהֶם צִנְצֶנֶת הַמָּן אָמַר לָהֶם אַתֶּם רְאוּ דְּבַר ה', שִׁמְעוּ לֹא נֶאֱמַר אֶלָּא רְאוּ, בָּזֶה נִתְפַּרְנְסוּ אֲבוֹתֵיכֶם, הַרְבֵּה שְׁלוּחִין יֵשׁ לוֹ לַמָּקוֹם לְהָכִין מָזוֹן לִירֵאָיו:
לדרתיכם FOR YOUR GENERATIONS e. g., in the days of Jeremiah: when Jeremiah was rebuking them (the people), saying, “Why do you not engage yourselves with the Torah?”, and they answered him, “Shall we leave our work and engage ourselves with the Torah? From where shall we earn a living?”, he brought out to them the cruse of Manna and said to them, (Jeremiah 2:31) “[O Generation], see ye the thing of the Lord!” It is not said “Hear the word” but “See the thing”! — This thing is what your fathers were fed with. The Omnipresent God has many messengers (many means) to provide food for those who fear Him (Mekhilta d'Rabbi Yishmael 16:33).
I love laying in my bed in the Sukkah under the schach and sky and it feels like a hug. I appreciate the idea that Hashem's love is through His hashgacha pratis (as we find by chanukah, as the noda byehuda is maarich) a feeling which your shtikel puts into words (i feel like ופרוש עלינו סוכת שלומך has these kinds of beautiful huggy undertones as well)
Moadim lsimcha!
The commandment to be happy, according to the Gra, is the hardest one.