1. Sukkot starts on the 15th day of the Jewish month of Tishrei, commemorating the Exodus from Egypt, the construction of the Holy Tabernacle and the 40 year wandering in the Sinai Desert. Sukkot (סכות), and the Sukkah (סכה), which is a Jewish ritual hut, are named after the first stop of The Exodus – Sukkota (סכותה). The Hebrew root of Sukkah (סכה) is "wholesomeness” and "totality” (סך), the "shelter” of the tabernacle (סכך), "to anoint” (סוך), "divine curtain/shelter” (מסך) and "attentiveness” (סכת).
2. The first recorded 7 day Sukkot celebration was – following the 5th century BCE Cyrus Edict - in Nehemiah 8:17: "And all the congregation of them that were come again out of the captivity made booths, and sat under the booths: for since the days of Joshua the son of Nun (13th-14th century BCE) unto that day had not the children of Israel done so. And there was very great gladness.”
3. Sukkot is the 3rd Jewish holiday – following Rosh Hashanah and Yom Kippur - in the month of Tishrei, the most significant Jewish month (Rosh Hashanah, Yom Kippur, Sukkot and Simchat Torah). According to Judaism, the number 3 represents divine wisdom, stability, permanence, integration and peace. Three is the total sum of the basic odd (1) and even (2) numbers. The 3rd day of the Creation was blessed twice; God appeared on Mt. Sinai 3 days following Moses' ascension to the mountain; there are 3 parts to the Bible, 3 Jewish Patriarchs, 3 pilgrimages to Jerusalem, etc.
4. Sukkot (the Feast of Tabernacles) is the 3rd Jewish pilgrimage, commemorating the post-Exodus forty year wandering in the desert, a holiday of happiness, hope, optimism and harvest. It follows the pilgrimage of Passover - the holiday of liberty, the birth of the Jewish nation and spring, and the pilgrimage of Shavou'ot (Pentecost) – the holiday of the Torah and national maturity/responsibility.
5. Columbus Day is celebrated around Sukkot. According to "Columbus Then and Now" (Miles Davidson, 1997, p. 268), Columbus arrived in America on Friday afternoon, October 12, 1492, the 21st day of the Jewish month of Tishrei, the Jewish year 5235, the 7th day of Sukkot, Hosha'na' Rabbah, which is a day of universal deliverance and miracles. Hosha' (הושע) is the Hebrew word for "deliverance” and Na' (נא) is the Hebrew word for "please." The numerical value of Na' is 51, which corresponds to the celebration of Hosha'na' Rabbah on the 51st day following Moses' ascension to Mt. Sinai.
6. Sukkot is a universal holiday, inviting all peoples to come on a pilgrimage to Jerusalem, as expressed in the reading (Haftarah) of Zechariah 14: 16-19 on Sukkot's first day. It is a holiday of peace - the Sukkah of Shalom (שלום). Shalom is one of the names of God. Shalem (שלם) – wholesome and complete in Hebrew - is one of the names of Jerusalem (Salem). According to Sukkah tractate of the Mishnah (the oral Torah), the 70 sacrificial bulls of Sukkot represent the pilgrimage of 70 nations to Jerusalem; a demonstration of universal solidarity and comity.
7. The Sukkah symbolizes the Chuppah – the Jewish wedding canopy – and the renewed vows between God and the Jewish People. While Yom Kippur represents God's forgiveness of the Golden Calf Sin, Sukkot represents the reinstatement of Divine Providence over the Jewish People. Sukkot is called Zman Simchatenou – time of our joy - and mandates Jews to rejoice (והיית אך שמח). The numerical value of the Hebrew word for "mandates” - "ach” אך – is 21, which is the number of days between Rosh Hashanah and the end of Sukkot.
8. The Sukkah (ritual hut) does not have a concrete roof, but is covered with branches of trees, representing the divine clouds which sheltered/shielded the Jewish people during the forty years in the desert, signifying the access to God, and the trust in God's guardianship. Hence the name of Sukkot: the shadow of faith and security (צילא דמהימנותא). The Hebrew word for roof (which is not allowed in Sukkot) is גג ("gag" - a synonym to "silence" and "shut up" in English), which some interpretations relate to the name of the Amalekite king, Agag and to Gog and Magog, the spiritual adversaries of the values of Sukkot.
9. The House of David is compared to a Sukkah/tabernacle (Amos 9:1-15), representing the central vision of the ingathering of Jews to their land, Zion, the Land of Israel. Sukkot is the holiday of harvesting – Assif (אסיף)- which also means "ingathering” (אסוף) in Hebrew. The four sides of the Sukkah represent the global Jewish community, which ingathers under the same roof/shelter. The construction of the Sukkah and Zion are two of the 248 Jewish Do's (next to the 365 Don'ts). Sukkot – just like Passover – commemorates Jewish sovereignty and liberty. Sukkot highlights the collective responsibility of the Jewish people, complementing Yom Kippur's and Rosh Hashanah's individual responsibility. Humility – as a national and personal prerequisite - is accentuated by the humble Sukkah. Sukkot provides the last opportunity for the annual repentance.
10. The seven days of Sukkot are dedicated to the 7 Ushpizin, distinguished guests (origin of the words Hospes and hospitality): Abraham, Isaac, Jacob, Joseph, Moses, Aaron and David. They defied immense odds in their determined pursuit of ground- breaking faith and principle-driven initiatives. The Ushpizin should constitute role models for contemporary leadership.
To read more on Sukkot, the Jewish meaning of "holiday,” additional Jewish holidays, the Sabbath, the Jubilee and annual fasting days: http://amzn.to/1mwxchc.