Sukkot begins on the 15th day of the Hebrew month of Tishrei, which is 5 days after Yom Kippur. Sukkot was originally a harvest festival at which time the farmer would celebrate the reaping of the seasonal fruit and the gathering of the vintage. Later the holiday took on a historical meaning. The sukkah served to recall the frail shelters that the Hebrews inhabited during their sojourn in the wilderness. Thus it became customary to build temporary quarters every year to recall the Exodus.
Where you live determines the length and celebration of Sukkot. Most of the world observes the festival for 9 days - the first two and the last two days being the most important. In Israel the festival is only celebrated for 8 days. In fact, many Jewish holidays are celebrated a day longer outside of Israel.
Why? This is because the Jewish month follows the cycle of the moon: a 'new moon' means a new month. Ideally (and the way it was done for the first thousand years of Jewish history) to determine the new month witnesses came to the Sanhedrin and testified that they saw the 'new moon'. The Sanhedrin would then establish day as Rosh Chodesh, the first day of the month.
Now, Jewish months can either be 29 or 30 days, depending on when the new moon of the next month is sighted. So if you were far away from Jerusalem, you would not know what day had been pronounced the first of the month. Consequently, you would not know which day the holidays started, and you might be one day off. So, Jews outside of Israel celebrated two days of the festival instead of one, since one of the two days was certainly the right day.
Today, even though we have a set calendar that tells us exactly when the holiday is, we still follow the old custom of our ancestors, who kept two days instead of one.
The next sukkot is October 12, 2011, followed by September 30, 2012 and September 18, 2013.
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