1. In general the holidays are characterized by joy. During the holiday of Sukkos the special additional festivities of the Simchas Bais HaShoeivah, were held in the Temple. Our Sages explain that the rejoicing at this occasion was particularly great, declaring (Sukkah 51a), “He who has not seen the rejoicing at the place of the Simchas Bais HaShoeivah (water-drawing) has never seen rejoicing in his life.” Although the Temple is destroyed, each Jew possesses a spiritual Temple (Shalah 69a) which is complete in the present time; hence, it is a Jewish custom to hold Simchas Bais HaShoeivah celebrations in these times. Furthermore, there is an advantage to the rejoicing of the present age. Since the festivities of the Simchas Bais HaShoeivah were accompanied by the playing of flutes and other musical instruments, they were not held on Shabbos or on Yom Tov. However, since the celebrations of Simchas Bais HaShoeivah in the present time is not connected with musical instruments, it can be held on the first night of Sukkos as well. Hence, not only the joy of the festivals (which applies to all Yomim Tovim) which are “festivals of rejoicing” and of Sukkos (in particular) which is “the season of our rejoicing,” but also the happiness of Simchas Bais HaShoeivah (which is even greater than the Simchah of “the season of our rejoicing”) begins on the present night.
This also applies to the Mitzvah of Hakhel. The Rambam (Hil. Chagigah Ch. 3) writes: “It is a positive commandment to gather together all of Israel: men, women, and children after the Shemitah year when they journey [to Yerushalayim] for the festival [of Sukkos] ... as the Torah states “at the end of every seven years, in the time of the Shemitah year, in the holiday of Sukkos, when all Israel come to appear [before the L-rd] .... gather the people together, men, women, and children, and the stranger in your midst... “ (Devarim 31:10-12) During the time of the Temple, this assembly was not held on Yom Tov (Sotah 41a) because certain provisions connected with Hakhel were forbidden on Yom Tov (Yerushalmi Megillah 1:4; also note Rashi Sotah 41b). However, at present, our Hakhel which recalls the Hakhel of the Temple, and gathers together men, women, and children, can also be held on the first day of Yom Tov.
2. There is an added factor which contributes to the celebration of Sukkos in the present year. Shabbos, which is called “the day of your rejoicing,” follows directly after the first two days of Sukkos (when Shehechiyanu is recited). Thus, there are three straight days marked by special rejoicing.
The happiness of the present occasion is also enhanced by the fact that we have begun a leap year, a year with thirteen months. The month of Tishrei includes many general services which are drawn down throughout the entire year to come. (This concept is alluded to in the name Tishrei which contains the same letters as the word “Raishes” meaning the head of. [The month of Tishrei carries out a function similar to the role played by the head in the human body.])
Similarly, the rejoicing of the holiday of Sukkos is the source of joy for all of the coming year. Since the present year has an extra month, the rejoicing of Sukkos must be even greater than usual, thereby generating happiness for that period as well.
Hence, in addition to the joy of the festivals, and the joy of Sukkos, the joy of Simchas Bais HaShoeivah, the joy of Hakhel, there are special factors (Shabbos, leap year) connected with the present year which enhance our celebration of the festival. Since the celebration of Sukkos in this manner is a command of G-d, He surely has given us the potential, aid, and blessing to celebrate them fully. We can celebrate “the season of our rejoicing” with great joy and draw down this joy into the entire year to come.
Furthermore, this joy will prepare and hasten the revelation of the ultimate joy, the coming of Mashiach. In the near future, all the Jews, together with G-d, will leave Golus in the spirit of Hakhel, with “our youth and our elders, our sons and our daughters”, “a great congregation will return there.” This is dependent upon our service in the time of Golus, and particularly, in the present times, in our rejoicing in the Simchas Bais HaShoeivah and the Joy of Hakhel. From this we will proceed with great joy to the coming of Mashiach, and we will thank G-d for “sustaining us and enabling us to reach this occasion.”