Why do we read Kohelet (Ecclesiastes), a book that flirts with the idea that life is futile and proclaims, “utter vanity, all is vanity” (1:2), on Succot, which is supposed to be a joyful holiday?
Some scholars point out that the other four megillot are read on different festivals and conclude that Kohelet and Succot were paired together by default. But, the Levush, Rabbi Mordechai Yaffe (16th century Poland), finds a deeper connection: Succot is called the Season of our Rejoicing and Kohelet reminds us to be happy with what we have. “Whenever a man does . . . get enjoyment out of all his wealth, it is a gift of God” (Kohelet 3:13).
Another suggestion is that Succot is the Festival of Gathering, of completing the harvest — a natural time to look back. Tradition attributes Kohelet to King Solomon and the Midrash says that he wrote Kohelet in his old age. Solomon was meditating on the harvest of his life; on Succot, we look back, joyfully, gratefully but also reflectively on the harvest of the past year.