The Festival of Sukkot begins on Tishri 15, the fifth day after Yom Kippur. It is quite a drastic transition, from one of the most solemn holidays in our year to one of the most joyous.
The word "Sukkot" means "booths," and refers to the temporary dwellings that we are commanded to live in during this holiday. The name of the holiday is frequently translated "The Feast of Tabernacles," which, like many translations of technical Jewish terms, isn't terribly useful unless you already know what the term is referring to. The Hebrew pronunciation of Sukkot is "Sue COAT," but is often pronounced as in Yiddish, to rhyme with "BOOK us."
Like Passover and Shavu'ot, Sukkot has a dual significance: historical and agricultural. The holiday commemorates the forty-year period during which the children of Israel were wandering in the desert, living in temporary shelters. Sukkot is also a harvest festival, and is sometimes referred to as Chag Ha-Asif, the Festival of Ingathering.
The festival of Sukkot is instituted in Leviticus 23:33 et seq. No work is permitted on the first and second days of the holiday. (See Extra Day of Holidays for an explanation of why the Bible says one day but we observe two). Work is permitted on the remaining days. These intermediate days on which work is permitted are referred to as Chol Ha-Mo'ed, as are the intermediate days of Passover.
In honor of the holiday's historical significance, we are commanded to dwell in temporary shelters, as our ancestors did in the wilderness. The commandment to "dwell" in a sukkah can be fulfilled by simply eating all of one's meals there; however, if the weather, climate, and one's health permit, one should live in the sukkah as much as possible, including sleeping in it.
A sukkah must have at least three walls covered with a material that will not blow away in the wind. Canvas covering tied or nailed down is acceptable and quite common in the United States. A sukkah may be any size, so long as it is large enough for you to fulfill the commandment of dwelling in it. The roof of the sukkah must be made of material referred to as sekhakh (literally, covering). To fulfill the commandment, sekhakh must be something that grew from the ground and was cut off, such as tree branches, corn stalks, bamboo reeds, sticks, or two-by-fours. Sekhakh must be left loose, not tied together or tied down. Sekhakh must be placed sparsely enough that rain can get in, and preferably sparsely enough that the stars can be seen, but not so sparsely that more than ten inches is open at any point or that there is more light than shade. The sekhakh must be put on last.
Many Americans, upon seeing a decorated sukkah for the first time, remark on how much the sukkah (and the holiday generally) reminds them of Thanksgiving. This is not entirely coincidental. Our American pilgrims, who originated the Thanksgiving holiday, were deeply religious people. When they were trying to find a way to express their thanks for their survival and for the harvest, they looked to the Bible for an appropriate way of celebrating and based their celebration in part on Sukkot. (Nifty facts they don't teach you in public school!)
List of Dates
Sukkot will occur on the following days of the Gregorian calendar:
Jewish Year 5764: sunset October 10, 2003 - nightfall October 17, 2003
Jewish Year 5765: sunset September 29, 2004 - nightfall October 6, 2004
Jewish Year 5766: sunset October 17, 2005 - nightfall October 24, 2005
Jewish Year 5767: sunset October 6, 2006 - nightfall October 13, 2006
Jewish Year 5768: sunset September 26, 2007 - nightfall October 3, 2007
http://www.jewfaq.org/holiday5.htm