Adonai said to Moshe, "Tell the people of Isra'el, 'On the fifteenth day of this seventh month is the feast of Sukkot for seven days to Adonai. On the first day is to be a holy convocation; do not do any kind of ordinary work...on the eighth day you are to have a holy convocation and bring and offering made by fire to Adonai; it is a day of public assembly; do not do any kind of ordinary work...On the first day you are to take choice fruit, palm fronds, thick branches, and river-willows, and celebrate in the presence of Adonai your God for seven days. You are to observe it as a feast to Adonai seven days in the year; it is a permanent regulation, generation after generation; keep it in the seventh month. You are to live in sukkot (booths) for seven days; every citizen of Isra'el is to live in a sukkah, so that generation after generation of you will know that I made the people of Isra'el live in sukkot when I brought them out of the land of Egypt; I am Adonai your God.'"
-from Leviticus 23:33-43
The word sukkot means "booths". These booths were temporary dwelling places. Some Bibles translate this word as "tabernacles".
The booths we build on Sukkot serve two purposes. First, they remind us of when the Israelites lived in booths as they wandered in the desert for forty years, totally dependent upon God for food, water, and clothing, and direction (Leviticus 23:43, Deuteronomy 1:33, Deuteronomy 8:2-4). Second, they remind us that our human, earthly bodies are but temporary, flimsy dwelling places for our spirits.
Some Israelites would build booths in their orchards, sleeping there to help keep animals away during the fruit harvest. This time of year was already a time of booth making; God uses the custom in his own way.
Sukkot celebrates the fruit harvest (similarly to how Pesach celebrated the barley harvest, and Shavuot celebrated the wheat harvest).
But Sukkot is an appointed time that can be much more clearly understood by understanding its prophetic signifigances. Not only does scripture relate it to events yet to come, but Yeshua used its rabbinical traditions as a backdrop for some of his most dramatic teaching.
Isaiah 56:6-7 reads:
"And the foreigners who join themselves to Adonai
to serve him, to love the name of Adonai,
and to be his workers,
all who keep Shabbat and do not profane it,
and hold fast to my covenant,
I will bring them to my holy mountain and make them joyful in my house of prayer;
their burn offerings and sacrifices
will be accepted on my altar;
for my house will be called
a house of prayer for all peoples."
This theme of the gentiles worshipping God appears several other times in the prophets. Nowhere, however, is it as concrete as at the end of the book of Zechariah.
Finally, everyone remaining from all the nations that came to attack Yerushalayim will go up every year to worship the king, Adonai-Tzva'ot [Lord of Hosts], and to keep the festival of Sukkot. If any of the families of the earth does not go up to Yerushalayim to worship the king, Adonai-Tzva'ot, no rain will fall on them.
Two traditions came out of this passage. First, Sukkot is seen as a holy day for joyously celebrating the time when God will be worshipped by all the earth. Second, Sukkot includes many prayers for water and rain. In Israel, this time of year has Summer's harvests ending, and the rainy planting season is approaching.
In this passage God directs the Israelites to sacrifice 70 bulls during the eight days of Sukkot, as well as an assortment of other animal sacrifices. Because of how Zechariah relates Sukkot to a time when all the gentile nations will worship God at his temple, the rabbis decided these 70 bulls represented the traditional 70 gentile nations.
The seventh chapter gospel of John records what Yeshua did in Jerusalem on one Sukkot (verse 2). Yeshua arrives in Jerusalem halfway through the eight days of Sukkot (verse 14). He teaches in the temple and arguements happen. Then, on the seventh day (called Hoshana Rabbah) he begins a new speech (verses 37-39). Hoshana Rabah (which means "the great praise") was the climax of the Temple rituals for Sukkot. One of these rituals was the water drawing ceremony. Yeshua had been waiting for its completion.
For the six prior days, a priest would go to the pool of Shiloach and fill a pitcher with water. The water was brought back to the Temple court, where it was poured into a basin at the foot of the altar amidst prayers for water and rain. On Hoshana Rabbah this ritual happened again, then the basin of water was poured onto the hot altar. The water would turn to steam and rise in a cloud from the altar. There was already a Jewish tradition interpreting the prayers for water as also asking for God's Spirit. This noisy, visible path of water leading up and down from the altar was especially seen as appropriate for praying for God's Spirit and the coming messiah, with Psalms 113-118, Isaiah 12:3, and other prayers. The entire Israelite nation (Deuternomy 16:16) was in the temple courts in an ecstatic celebration, asking for the messiah to come.
There was also bright illumination in the Temple during Sukkot. On Hoshana Rabbah four 75-foot tall menorah were lit.
Then Yeshua "stood and cried out, 'If anyone is thirsty, let him keep coming to me and drinking! Whoever puts his trust in me, as the Scripture says, rivers of living water will flow from his inmost being!'" (John 7:37-38).
Yeshua was saying, "You are praying for water and rain, and I am the answer to those prayers! You are praying for your messiah, and I am here!" The crowd clearly undertood (John 7:40-44). Yeshua was using water, a symbol of Sukkot, to make his point.
Realize that most scholars agree that John 7:53-8:11 was an inserted story, to see Yeshua continuing his speech in John 8:12 after the uproar had quieted some. "I am the light of the world: whoever follows me will never walk in darkness but will have the light which gives life." Again, Yeshua was clearly using light, another symbol of Sukkot, to restate his message. The Pharisees argue with him through the rest of the eighth chapter of John. Then Yeshua leaves the Temple court and starts more trouble by healing a blind man at the pool of Shiloach (John 9). Yeshua continues teaching until John 10:21. At that point, the narration skips ahead until Hanukkah.
Since Sukkot was a harvest festival we can continue to give thanks for God's provision.
We can pray for others to recognize Yeshua, as his most direct claims to be messiah happened during Sukkot. An appropriate time for such prayers is during the traditional waving of the lulav (branches of palm, myrtle, and willow) in all directions, which is understood as a plea for God's Spirit to fill the earth.
Most of all, we can pray for our own filling with God's Spirit, even to a quantity as rivers! During the recent appointed times of Rosh Hashanah and Yom Kippur the purity of our relationship with God was renewed. Now we are ready for a great filling of God's spirit.
This question seems harmless enough, but actually requires a bit of scripture study whose result will be surprising to many people!
In First Chronicles 24:3-19, we read about the establishment of the 24 clans of the Aharonic priesthood. The clans, also called divisions, took turns in weekly service. On the pilgrimage feasts all twenty-four divisions worked in the Temple.
In Luke 1:5 we read that Z'kharyah, father of Yochanan the Immerser, was of the Aviyah division. 1 Chronicles 24:10 tells us this was the 8th division.
So we must consider two scenarios: the week of Z'kharyah's service mentioned in the first chapter of Luke could have been either his first or second annual time of service.
The first rotation of weeks of service began at the beginning of the month of Nisan. Since the 3rd and 9th weeks (Pesach and Shavuot) had all divisions present, Abijah, as the 8th division, would serve the first of its twice-per-year weeks on the 10th week since Nisan 1. This would be the week after Shavuot—the second week of Sivan. So it was a week later, when Z'kharyah returned home, that Elizabeth became pregnant; Yochanan was conceived at the end of Sivan, two weeks after Shavuot.
Six months later (Luke 1:24-26) is the end of the 3rd month, Kislev. Yeshua is conceived at Chanukah time.
An average pregnancy is 285 days, which is 9 1/2 Hebrew months. Counting from the end of Sivan we arrive at mid-Nisan: Yochanan was born during Pesach! And counting 285 days from the end of Kislev we get to mid-Tishri: Yeshua was born during Sukkot!
The second rotation of weeks of service began at the beginning of the month of Tishri. Two weeks are again postponed before the Aviyah division has its turn, this time for Yom Kippur and Sukkot. Ten weeks after Tishri 1 is the middle of Kislev. In this case it is Yochanah who is conceived at Chanukah time, and born at Sukkot. And in this second scenario, Yeshua is conceived at the end of Tevet, and born in mid-Cheshvan: neither time has a holiday.
The first scenario makes much more sense. Shepherds would not be out with their flocks at night in mid-Cheshvan. This is winter, and shepherds only stayed out overnight with their flocks earlier in the year. Neither would the Romans perform a census in winter, when many roads were unusable.
Thus we can say with quite a bit certainty that Yeshua was born during Sukkot.
Sukkot is an odd holiday because it lasts for seven days, but still has an eighth day! This is odd, but it is what Leviticus 23:39 says. It is sort of like two different holidays, but they are related. The key to understanding this curiosity is that events in Yeshua's life were foreshadowed by the holidays. The first day of Sukkot foreshadowed Yeshua's birth: on the day of tabernacles, God came to "tabernacle among us" (John 1:14). Sukkot was also the time when the written Word of God was read to the populace; thus the arrival of the living Word of God was also proclaimed at that time, to all sorts of different people. And on the eighth day, when Yeshua was circumcised, it was something different yet related.
Also note that because Z'kharyah served in the week after Shavuot, then just as the book of Acts can be described as "What God gave to his people after Pentecost", the same is true of the Book of Luke!
Finally, realize that what we just did was use historical records, including scripture, to determine Yeshua's birth within a few weeks, and then used the assumption that scriptural holidays foreshadow events in the Messiah's life to fix a precise date for Yeshua's birth. We have no historical evidence to prove that Yeshua was carried full term, but since other events in his life were so clearly foreshadowed by Pesach, First Fruits, Shavuot, and Yom Kippur then it is reasonable to assume his birth and circumcision happened on the 1st and 8th days of Sukkot instead of "missing" those dates by a few days.
A reasonable next question is "In what year was Yeshua born?". The answer is clear if we accept the following two propositions, which most historians agree are true: first, that a Roman census happened every 14 years; second, that Josephus recorded history accurately when he said that Herod died on the night of an eclipse of the moon during a Hebrew fast. If these are both true, the other details fall into place.
An eclipse of the moon only can happen in the middle of a Hebrew month, and the only Hebrew fast in the middle of a Hebrew month is the Fast of Esther. Astronomical calculations agree there was a lunar eclipse in the spring of 4 BC at this date. Moreover, in nearby years there were no other lunar eclipses at the Fast of Esther. Thus Herod died in the spring of 4 BC. Matthew tells us Herod was still alive when Yeshua was born (2:1) and was probably almost 2 years old while Herod was still alive (2:16). Some historians believe that the Jews of that time would say an infant was "1 year old" when it was born, counting pregnancy as your first year of life. But we can still say that Yeshua was born before 4 BC.
Luke 2:1-5 mentions a census of Quirinius which was his "first" census. When Quirinius became Governor of Syria in 6 AD he took a (second) census. The previous census year would be 8 BC, at which time Quirinius also "governed" Syria as a consul in Rome in charge of suppressing the rebellions against Rome in Asia. Some scholars believe that the census of 8 BC was an odd one, in which Augustus ordered a coin of tribute after some large rebellions were squashed. This corresponds with some 2nd-century versions of Luke that rephrase Luke 2:1 as "At that time, Caesar Augustus ordered that all men should come to their own town and bring the governor a silver coin as a sign of subjection to the empire." In any case, there was a census in 8 BC. And so we know Yeshua was born in 8 BC.
We should also note that the Hebrew year that began in the autumn of 8 BC was not a year with a leap month, which helps defend our earlier counting to determine Yeshua's birth day.