So we Slept in Sukkot, What's the Big Deal?? Why we really Celebrate this Holiday

לְמַעַן֮ יֵדְע֣וּ דֹרֹֽתֵיכֶם֒ כִּ֣י בַסֻּכּ֗וֹת הוֹשַׁ֙בְתִּי֙ אֶת־בְּנֵ֣י יִשְׂרָאֵ֔ל בְּהוֹצִיאִ֥י אוֹתָ֖ם מֵאֶ֣רֶץ מִצְרָ֑יִם אֲנִ֖י ה' אֱלֹקֵיכֶֽם׃

Leviticus 23:43

in order that future generations may know that I made the Israelite people live in booths when I brought them out of the land of Egypt, I the LORD your God.

רש"י על ויקרא כ״ג:מ״ג:א׳

(א) כי בסכות הושבתי. עַנְנֵי כָבוֹד (שם; מכילתא י"ב):

Rashi on Leviticus 23:43:1

That I made the Israelite people live in booths — These [sukkot] are "Clouds of Glory".

רשב"ם על ויקרא כ״ג:מ״ג

(א) למען ידעו דורותיכם - פשוטו כדברי האומרים במסכת סוכה סוכה ממש. וזה טעמו של דבר: ... למען תזכרו - כי בסוכות הושבתי את בני ישראל במדבר ארבעים שנה - בלא יישוב ובלא נחלה ומתוך כך תתנו הודאה למי שנתן לכם נחלה ובתים מלאים כל טוב ואל תאמרו בלבבכם כחי ועוצם ידי עשה לי את החיל הזה... ולכך יוצאים מבתים מלאים כל טוב בזמן אסיפה ויושבין בסוכות לזכרון שלא היה להם נחלה במדבר ולא בתים לשבת.

Rashbam on Leviticus 23:43

So that your generations will know— The simplest explanation of this is according to those who say in Masechet Sukkah that סוכה refers literally to a סוכה [booth]. And here is the reason... In order that you will remember that “I caused the Children of Israel to dwell in booths” in the desert for forty years without a place to settle and without property, and therefore you should give thanks to [G-d] who gave you property and your houses full of good things, and so that you won’t say in your heart “my strength and the power of my hands made these great things for me”... therefore we leave our full houses that are full of good at the time that we gather our crops and we sit in סוכות to remember that our ancestors did not have property in the desert and no houses to sit in.

סוכה י״א ב:י״ד

זֶה הַכְּלָל: כׇּל דָּבָר שֶׁמְּקַבֵּל טוּמְאָה כּוּ׳. מְנָא הָנֵי מִילֵּי? אָמַר רֵישׁ לָקִישׁ, אָמַר קְרָא: ״וְאֵד יַעֲלֶה מִן הָאָרֶץ״. מָה אֵד — דָּבָר שֶׁאֵינוֹ מְקַבֵּל טוּמְאָה וְגִידּוּלוֹ מִן הָאָרֶץ, אַף סוּכָּה — דָּבָר שֶׁאֵין מְקַבֵּל טוּמְאָה וְגִידּוּלוֹ מִן הָאָרֶץ.

Sukkah 11b:14

§ We learned in the mishna: This is the principle with regard to the roofing of a sukka: One may not roof the sukka with anything that is susceptible to ritual impurity or whose growth is not from the ground. The Gemara asks: From where are these matters with regard to the roofing of a sukka derived? Reish Lakish said that the verse states: “And there went up a mist from the earth, and watered the entire face of the ground” (Genesis 2:6); just as mist, i.e., a cloud, is a substance not capable of contracting ritual impurity, and its growth is from the ground, i.e., arises from the ground, so too, the roofing of the sukka must consist of a substance that is not susceptible to ritual impurity and its growth is from the ground. Since the mitzva of sukka evokes the clouds of glory with which God enveloped the Israelites in the desert, the legal status of roofing should be like that of a cloud.

סוכה י״א ב:ט״ו

הָנִיחָא לְמַאן דְּאָמַר עַנְנֵי כָבוֹד הָיוּ. אֶלָּא לְמַאן דְּאָמַר סוּכּוֹת מַמָּשׁ עָשׂוּ לָהֶם, מַאי אִיכָּא לְמֵימַר? דְּתַנְיָא: ״כִּי בַסּוּכּוֹת הוֹשַׁבְתִּי אֶת בְּנֵי יִשְׂרָאֵל״, עַנְנֵי כָבוֹד הָיוּ, דִּבְרֵי רַבִּי אֱלִיעֶזֶר. רַבִּי עֲקִיבָא אוֹמֵר: סוּכּוֹת מַמָּשׁ עָשׂוּ לָהֶם. הָנִיחָא לְרַבִּי אֱלִיעֶזֶר, אֶלָּא לְרַבִּי עֲקִיבָא מַאי אִיכָּא לְמֵימַר?

Sukkah 11b:15

The Gemara asks: This works out well according to the one who said that the sukkot mentioned in the verse: “I made the children of Israel to reside in sukkot” (Leviticus 23:43), were clouds of glory, as it is reasonable that the roofing of the sukka is modeled after clouds. However, according to the one who said that the children of Israel established for themselves actual sukkot in the desert, and the sukkot of today commemorate those, what can be said? According to that opinion, there is no connection between a sukka and a cloud. As it is taught in a baraita that the verse states: “I made the children of Israel to reside in sukkot”; these booths were clouds of glory, this is the statement of Rabbi Eliezer. Rabbi Akiva says: They established for themselves actual sukkot. This works out well according to Rabbi Eliezer; however, according to Rabbi Akiva what can be said?

שמות י״ב:ל״ז

וַיִּסְע֧וּ בְנֵֽי־יִשְׂרָאֵ֛ל מֵרַעְמְסֵ֖ס סֻכֹּ֑תָה כְּשֵׁשׁ־מֵא֨וֹת אֶ֧לֶף רַגְלִ֛י הַגְּבָרִ֖ים לְבַ֥ד מִטָּֽף׃

Exodus 12:37

The Israelites journeyed from Rameses to Succoth, about six hundred thousand men on foot, aside from children.

בראשית ל״ג:י״ז

וְיַעֲקֹב֙ נָסַ֣ע סֻכֹּ֔תָה וַיִּ֥בֶן ל֖וֹ בָּ֑יִת וּלְמִקְנֵ֙הוּ֙ עָשָׂ֣ה סֻכֹּ֔ת עַל־כֵּ֛ן קָרָ֥א שֵׁם־הַמָּק֖וֹם סֻכּֽוֹת׃ (ס)

Genesis 33:17

But Jacob journeyed on to Succoth, and built a house for himself and made stalls for his cattle; that is why the place was called Succoth.

שמות י״ב:מ׳

וּמוֹשַׁב֙ בְּנֵ֣י יִשְׂרָאֵ֔ל אֲשֶׁ֥ר יָשְׁב֖וּ בְּמִצְרָ֑יִם שְׁלֹשִׁ֣ים שָׁנָ֔ה וְאַרְבַּ֥ע מֵא֖וֹת שָׁנָֽה׃

Exodus 12:40

The length of time that the Israelites lived in Egypt was four hundred and thirty years;

שמות י״ב:ל״ט

וַיֹּאפ֨וּ אֶת־הַבָּצֵ֜ק אֲשֶׁ֨ר הוֹצִ֧יאוּ מִמִּצְרַ֛יִם עֻגֹ֥ת מַצּ֖וֹת כִּ֣י לֹ֣א חָמֵ֑ץ כִּֽי־גֹרְשׁ֣וּ מִמִּצְרַ֗יִם וְלֹ֤א יָֽכְלוּ֙ לְהִתְמַהְמֵ֔הַּ וְגַם־צֵדָ֖ה לֹא־עָשׂ֥וּ לָהֶֽם׃

Exodus 12:39

And they baked unleavened cakes of the dough that they had taken out of Egypt, for it was not leavened, since they had been driven out of Egypt and could not delay; nor had they prepared any provisions for themselves.

ירמיהו ב׳:ב׳

הָלֹ֡ךְ וְקָֽרָאתָ֩ בְאָזְנֵ֨י יְרוּשָׁלִַ֜ם לֵאמֹ֗ר כֹּ֚ה אָמַ֣ר ה' זָכַ֤רְתִּי לָךְ֙ חֶ֣סֶד נְעוּרַ֔יִךְ אַהֲבַ֖ת כְּלוּלֹתָ֑יִךְ לֶכְתֵּ֤ךְ אַחֲרַי֙ בַּמִּדְבָּ֔ר בְּאֶ֖רֶץ לֹ֥א זְרוּעָֽה׃

Jeremiah 2:2

Go proclaim to Jerusalem: Thus said the LORD:
I accounted to your favor
The devotion of your youth,
Your love as a bride—
How you followed Me in the wilderness,
In a land not sown.

ויקרא כ״ג:ל״ט

אַ֡ךְ בַּחֲמִשָּׁה֩ עָשָׂ֨ר י֜וֹם לַחֹ֣דֶשׁ הַשְּׁבִיעִ֗י בְּאָסְפְּכֶם֙ אֶת־תְּבוּאַ֣ת הָאָ֔רֶץ תָּחֹ֥גּוּ אֶת־חַג־ה' שִׁבְעַ֣ת יָמִ֑ים בַּיּ֤וֹם הָֽרִאשׁוֹן֙ שַׁבָּת֔וֹן וּבַיּ֥וֹם הַשְּׁמִינִ֖י שַׁבָּתֽוֹן׃

Leviticus 23:39

Mark, on the fifteenth day of the seventh month, when you have gathered in the yield of your land, you shall observe the festival of the LORD [to last] seven days: a complete rest on the first day, and a complete rest on the eighth day.

אורח חיים תרכ״ד:ה׳

והמדקדקים מתחילים מיד במוצאי י"ה בעשיית הסוכה כדי לצאת ממצוה אל מצוה: [מהרי"ל ומנהגים והגהות מיימוני פרק ב' דברכות מהרי"ו]:

Shulchan Arukh, Orach Chayim 624:5

5. A Jew that lights from a Gentile, They do not bless on it on Motzei Yom Kippur even though on Motzei Shabbos, They do bless on it. Because They do not bless on Motzei Yom Kippur except a flame that rested from before the day (of Yom Kippur) literally or a flame that was lit from it (a rested flame). And similar is one accustomed to light from Synagogue lanterns; furthermore, even if lit on Yom Kippur, if lit in a permitted matter like for a sick person, they are able to bless on it. Note (Rema): There are those ...