Kahal Chasidim She'aris Yaakov 
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Sukkos - We Need to Know...
If it would be up to human logic, we would celebrate Sukkos shortly after Pesach when the weather is warm and pleasant, to commemorate the first time we dwelled in huts, right after our departure from Egypt. But Hashem instructed us to wait until the fall, when the weather is cooler. He did this so that our act would be more meaningful. Had we gone outdoors during the summer, it would have appeared that we were doing so to enjoy the nice weather. Instead, Hashem told us to wait till the cooler weather comes so our actions would make it clear that we are dwelling in "booths" for Hashem's sake rather than our own (Tur O.C. 625).
The first Rebbe of Gur, the Chidushei Harim, gives another answer to why we do not celebrate sukkos right after Pesach. When the Torah, in Parshas Emor, describes the details of the Festival of Sukkos, Hashem instructs us to dwell for seven days in sukkos (booths) “…in order that future generations will know that I had you dwell in booths when I brought them out of Egypt” (Vayikra. 23:43).
The verse clearly implies that knowledge is one of the requirements for properly observing the festival.
Through an entire year we all struggle with our Evil Inclination. We fall time after time into transgressions. Since the Gemara states that a person doesn't commit a transgression unless a spirit of folly overtakes him (Sotah 3a), we can see that for the whole year a person is as if he is without knowledge. And, without knowledge, he is not able to properly fulfill the mitzvah of Sukkah.
Only after the atonement of Rosh Hashanah and Yom Kippur in the month of Tishrei, when a person is cleansed of his transgressions and has resolved to be a tzadik from now on, does he have the knowledge to properly fulfill the mitzvah of Sukkah.
There is a מחלקת (disagreement) in the Gemara (Sukkah 11b) as to what our Sukkahs commemorate. Rabbi Eliezer’s opinion is that we commemorate the clouds of glory with which HaShem protected Klal Yisrael while in the wilderness. Rabbi Akiva’s opinion is that we are commemorating the fact that Bnei Yisrael actually lived in Sukkahs in the desert on the way out of Egypt.
Rabbi Eliezer’s view is easily understandable. We relive HaShem's protection of us and give thanks to Him for it. But what about Rabbi Akiva? What exactly are we commemorating? Why is it significant that Bnei Yisrael happened to live in huts in the desert?
From amongst the many approaches to this difficulty there are two that we will mention in this essay; the Ramban and the Rashbam (both on Vayikra 23:43). The Ramban writes that we are noting that even though we lived in primitive huts in the desert, we still lacked nothing – HaShem provided us with everything we needed.
But the Rashbam adds another dimension to this. He writes that on Sukkos we remember that we did not always live in houses and cities and did not always have a hold in Eretz Yisrael. Once we re-sensitise ourselves to these facts, appreciating that even our very houses are from Hashem, we are imbued with a feeling of humility and thankfulness to Hashem.
We can now gain greater insight to the words of the Chidushei Harim. According to Rabbi Akivah's opinion that we are commemorating dwelling in "booths" during our travels through the wilderness; we are also remembering that everything we have is from Hashem and that we do and cause nothing. We celebrate this after Rosh Hashanah because at this time we are "cleansed" enough to truly have this knowledge, i.e., that everything comes from Hashem.
Reb Saddyah Gaon (in the reasons he gives to blowing the shofar) says, “The shofar summons us to the feeling of humility before Hashem's majesty and might, which are manifested by all things and by which our own lives are constantly surrounded.” We then come to Yom Kippur when we gain even greater humility. We actually come to realize how truly fragile we humans are that we can barely survive for 25 hours without food or drink.
We are now ready to sit in the Sukkah, since we have finally achieved דעת (knowledge). The early sefarim use the concept of “תכלות הידיע שנדע שלא נדע - the end of knowledge is to know that we do not (and cannot) know.” When we reach Sukkos we have such great insight that are able to see that as much as we can ever know, we actually know very little. How truly humbling and inspiring!
Once we've reached this level we can come to the Yom Tov of Simchas Torah, where we all proclaim, “אתה הראת לדעת כי יי הוא האלוקים אן עוד מלבדו - You have been shown, in order to know that Hashem, He, is G-d; there is none else besides Him.”