The sages of the Mishna were divided about this issue two thousand years ago. Rabbi Akiva thought that these were regular booths that Bnei Yisrael built in the desert. Rabbi Eliezer claimed that this referred to the Clouds of Glory that G-d brought to protect Bnei Yisrael from mountains, obstacles, animals, and other potential harms along the way.
These explanations are hard to understand. If these were real succot, what would be the reason every year to remember them? What was special about them? And even if we were talking about the Clouds of Glory that came miraculously, why do we celebrate a special holiday for this miracle in particular? The Torah tells us about many other miracles that our forefathers merited in the desert: The miracle of the manna ? the heavenly food that they ate in the desert, the miracle of Miriam?s well ? that provided them with drinking water throughout their journey, and others. In what way were the succot so unique that we celebrate a special holiday to remember them?
Let us ask one more question. There is a halacha (Jewish law) regarding succot that is unlike any other commandment: A person for whom eating or sleeping in the succa causes physical sorrow is exempt from being in a succa. For example, someone who lives in a very cold place or whose succa is full of mosquitoes can eat and sleep in his home as usual. Why? A person for whom giving charity or keeping Shabbat or eating matza on Pesach causes sorrow would not even imagine being exempt from these mitzvot. What is so special about the mitzvah of being in the succa?
To understand this, let us look at the two opinions we mentioned above ? actual booths or Clouds of Glory ? and see that they are two sides of the same coin. When Bnei Yisrael left Egypt, G-d placed them under His wings and they merited life accompanied by His special kindness. Their relationship with the Creator was simple: At any time, they could approach Moshe who had ?free access? to talk to G-d and look into their doubts. Simultaneously, G-d gave them mitzvot and directions to raise their spiritual level which reached its peak when they received the Torah on Mount Sinai. They lived inevery moment.
Along with this lofty spiritual sense came an amazing physical reality as well. An entire nation of millions of people (600,000 men between the ages of 20 ? 60, excluding women and children) walked through the desert. Where did they get food? Where did they get water? Clothes? Shelter? They merited heavenly miracles in these spheres as well: Food fell from the sky, water came up from the well, the clothing never wore out, and the succot were built.
In memory of this wonderful wholeness, of the journey through the desert under the wings of G-d Who accompanied us with extraordinary material abundance, we celebrate the festival of Succot. The holiday includes two sides of the coin: We are commanded to go out into nature and try to reenter the feeling of dependence on G-d and of being sheltered in His shadow as were Bnei Yisrael in the desert, but all this under the condition that there is no physical sorrow.
We try to recreate the spiritual experience our forefathers had in the desert: Perfect dependence on G-d that comes with physical comforts even in a barren desert. This is why we have that unique halacha that states that if a person feels sorrow sitting in his succa, he is exempt from this mitzvah.
Now we can better feel and understand that the holiday of Succot is not just a joyful holiday and a commemoration of miracles that occurred in the desert. It is a lofty, spiritual experience that comes at the perfect time: after Rosh Hashana and Yom Kippur when we felt the judgement and mercy of the Creator and our sins were atoned. Then we merit the Divine light that leads us to live in a different atmosphere, in the ambience of a succa that G-d shields, with the sense of the Clouds of Glory enveloping us and walking alongside us in every step of life, and in the great joy over being privileged to live in this great light, the light of the Creator that accompanies our lives in great love.