Begins at sundown on September 27. Sukkot begins on Tishri 15, five days after Yom Kippur. It is quite a drastic transition, going from one of the most solemn holidays in our year (Yom Kippur) to one of the most joyous (Sukkot).
Like Passover and Shavu'ot, Sukkot has both historical and agricultural significance. The holiday commemorates the forty-year of wandering after the exodus from Egypt, when the Israelites walked the desert building temporary shelters. It is also a harvest festival, sometimes referred to as Chag Ha-Asif, the Festival of Ingathering. Sukkot is one of three pilgrimage holidays, where Jews from all over the world travel to Jerusalem to visit Ha'Kotel, the Western Wall.
Tradition tells us that no work is permitted on the first and second days of the holiday, though 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.