WHERE DO WE GO FROM HERE?
THE YEAR BEGINS IN CHESHVAN
In many synagogues there is a custom to publicly proclaim the words, “And Jacob went on his way” three times at the beginning of each year: at the conclusion of Simchat Torah, at the end of Shabbat Bereishit, and on the seventh day of Cheshvan. This indicates that after all the holidays of Tishrei and the seventh of Cheshvan, the year has truly begun. Repeating it three times establishes the idea firmly in reality.
The seventh day of Cheshvan is the day we begin to request rain in the Amidah, the cardinal prayer of Judaism. Although we already began to acknowledge that God makes the “wind blow and the rain fall” on Shemini Atzeret/Simchat Torah, we only begin to explicitly request rain on the seventh day of Cheshvan. The reason for this delay is that when the Temple stood in Jerusalem, Jews from all over the Diaspora came to Jerusalem for the holiday of Sukkot and the request for rain had to wait until all the pilgrims were safely back home, as traveling in the rain would be very difficult.