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The Torah says:

You shall dwell in booths for seven days... so that your generations might know that I made the children of Israel dwell in booths. [Lev. 23:42-43]

The stated reason seems strange. It almost sounds like circular reasoning. Indeed, the Talmud, Midrashim and later commentaries say that the booths really refer to the clouds of glory God used to guide and shelter the people in the desert [Sifra, Emor 17:11; Mekhilta d'Rabbi Yishmael 12:35; Sukkah 11b]. These clouds are first mentioned in Exodus 13:21–22.

This also makes sense if we assume that God wanted future Jews to remember what He did for them during the Exodus from Egypt on all three pilgrimage festivals: On Pessah; the liberation from slavery in Egypt; on Shavuot, the giving of the Torah; and on Sukkot, the protection and sustenance during the trek in the desert.

Also, this is the only reference in the Torah to the Israelites actually dwelling in booths. Other references just mention the holiday and the four species.

Given all of the above, why do we celebrate Sukkot by building booths and dwelling in them?

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    I don't understand at all how this is "circular reasoning". I have no idea what you are confused about. We sit in booths forever one week a year to remember how we sat in booths as part of the Exodus. Just like how we eat matza for one week a year to remember... – Double AA♦ Sep 23 '20 at 12:55
  • The Tannaitic view I am referring to is that we did NOT sit "in booths as part of the Exodus.". – Maurice Mizrahi Sep 23 '20 at 15:29
  • What's the difference? We sit in booths to remember how we sat in "booths" made of clouds as part of the Exodus. I still don't understand what you are confused about. – Double AA♦ Sep 23 '20 at 15:30
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    If you know where I can purchase clouds of glory I'd be happy to make that my Sukkah this year instead. – Alex Sep 24 '20 at 0:06
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    Why do we celebrate Sukkot in booths ? - Because it's a harvest festival; one camps in the field, where one harvests. I'm leaving this as a comment because you're probably searching for some sourced answer, which I cannot provide. – Lucian Sep 24 '20 at 7:51
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It is because it reinforces our sense of emunah. It says in Gemara Succah on the verse, “In succahs shall you live for seven days” (Vayikra 23:42):

צא מדירת קבע ושב בדירת עראי

Depart from your permanent dwelling place and live in a temporary dwelling place.

Thus, When we leave the permanent and secure structure of our house and instead move into a temporary, rickety hut for the duration of Succos we are strengthening our belief in Hashem.

The Zohar 3:103b famously writes:

בְּשַׁעֲתָא דְּבַר נָשׁ יָתִיב בְּמָדוֹרָא דָּא, צִלָּא דִּמְהֵימְנוּתָא, שְׁכִינְתָּא פַּרְסָא גַּדְפָהָא עָלֵיהּ מִלְּעֵילָּא, וְאַבְרָהָם וַחֲמִשָּׁה צַדִּיקַיָּיא אָחֳרָנִין שַׁוְיָין מָדוֹרֵיהוֹן עִמֵּיהּ.

At the time when a person sits in this dwelling place, it is the shade of belief, the Divine presence spreads out on top of him from above and Avrohom and the five tzaddikim after him (i.e. a reference to the Ushpizin) come and dwell with him.

Thus, although sitting in Succahs first and foremost are reminder of the Clouds of Glory, they also serve as a reminder of our dependence on G-d and how we are steadfast in our faith towards Him.

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According to Rashi, the sukkahs represented the clouds of glory. However, rabbi Arnold Ehrlich disagreed. He felt that clouds are not huts.

He also felt that Sukkot was originally a harvest festival. When the holiday changed during second temple times, the Israelites, then traveling to the then small Jerusalem by pilgrimage, could not find an inn, used hastily constructing booth (sukkot), going on “strike.” In order to counter this, the Israelite leadership told everyone to live in a sukkah.

In addition, Ehrlich says that the reason why Jews dwell in sukkahs today is that ancient Israelites dwelt in them upon leaving Egypt (Leviticus 23:43).

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