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This is more for Hoshana Rabba and Shmini Atzeret than for Shabbat Sukkot, but I thought it was interesting enough to look into. There’s a minhag to say goodbye to the sukkah (in חוץ לארץ, on Shmini Atzeret):
I’m not going to deal with the Leviathan idea but rather with the idea that we have a ritual for the end of the mitzvah. That’s not something we usually do; we don’t say goodbye to the matzah or the menorah. We do have הבדלה after שבת, but that’s it. And the mishna seems to say that some sort of formal “end of Sukkot” is mandatory:
Rashi says it’s because we may still want to eat in the sukkah, and we have to show that the mitzvah is over, so we don’t transgress בל תוסיף:
But the Rambam doesn’t mention אין לו מקום אחר לאכול שם:
And Rabbi Schnall suggests that this requirement is the basis of our “Farewell to the Sukkah”:
And Rashi himself implies there’s something special about not sitting in the sukkah on Shmini Atzeret:
Similarly, the Targum Jonathan translates עֲצֶ֖רֶת as כְּנִישִׁין, ingathering, a holiday of our joy at going back into our houses:
Why? The Vilna Gaon connects the רגלים to the history of Israel as they left Egypt:
And that’s the key connection. שמיני עצרת represents leaving the ענני כבוד to start life “in the real world”. That, the Baal Hatanya said, was the problem with the מרגלים:
And that is how we look at the sukkah, and our exiting from it:
So we need to leave the sukkah, and even more so, to rejoice in leaving it:
And even more so, Shmini Atzeret pulls together the previous 21 days:
Leaving the sukkah and going back inside, to our quotidian lives, is a chance to pull together all we have accomplished in these 21 days of חגי תשרי and incorporate that growth into ourselves, which will help bring ימות משיח and our metaphoric banquet בסוכת עורו של לויתן.