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    There are 12 Jewish holidays, 5 biblical and 7 rabbinic. 

Each Jewish holiday has it's own list of observances, things you can and cannot do repeated every year, bringing into play the spiral element of going full circle back to where you were before, but with an element of change giving a possible spiritual influence of growth. The Jewish people observe the lunar year which has only 354 days, causing it to be 11 days shorter then the solar year. That is why leap year is observed, allowing the Jewish people to keep the holidays in their correct season as commanded in the Torah.


Biblical holidays are commanded in the Torah, therefore mandated that the Jewish people observe them.  By the end of the Torah, the Jewish people were just on the borders of their 'promised' land, not yet inhabiting it.  These holidays are independent of any experience inside their promised land.  There are 3 Festivals and 2 High Holidays also called the 'Days of Awe'.  A Festival commemorates the formative development of Israel as a nation, paralleling 3 different places the Jews lived before coming into Israel.  The Days of Awe don't remind the Jew of a specific experience but rather help them to become a more spiritually renewed individual.

Holy day

Information

Sedar plate of Pesach Jewish holidayPesach 
or
Passover
or
Feast of Unleavened
    Bread

 

Matza of Pesach Jewish holidayFirst place to live and grow spiritually was in Egypt, where they were for 210 years.

This Festival commemorates the leaving of the Jewish slaves from Egypt, to become a freed people inheriting their own land.  Therefore it is recognized as a holiday of freedom.
It's called Passover to recognize the passing over of their homes as the 'Angel of Death' began killing all of Egyptians firstborn both human and animal.  That was the final plague that caused Pharoh to let the Jews leave.

It is celebrated for 7 days in the land of Israel, or 8 days outside the land of Israel.  The observances for this Festival, such as the eating of 'mazzot' is to serve as a reminder of freedom.
 

Shavout 
or
Feast of Weeks

Second place to live and grow spiritually was at Mt. Sinai.

Called this because it comes 7 weeks after Passover, this day is considered the birthday of Jewish religion.  It is in honor of when the 10 commandments were given on Mt. Sinai.  The concept of truthfulness is recognized.  Clarity is often found for the individual for various aspects of their life during this festival.  One tradition observed is to stay up all night studying the Torah, to make up for the night before the giving of the 10 commandments at Mt. Sinai when everyone was sleeping.
 

Sukkot 
or
Feast of Tabernacles  


tabernacle building of Sukkot Jewish holiday

The third place to live and grow spiritually was for 40 years in the desert.

Sukkot, which translates "booths" or "tabernacles", is celebrated for 7 days as a form of recognition for living 40 years in the desert  in temporary dwellings or 'tabernacles'.

The theme is one of happiness. First because it's linked to the harvest festival but more importantly, because of the protection while living in the desert.  One observance is having the booth made with a thatched roof that you can see through to the stars.  Security and ultimately happiness for a Jew lies in their relationship to God, not in their material well being.
 

Rosh ha Shonah
or
First Day of Awe

The Jewish New Year in either September or October.  It is also considered the anniversary of the creation of Adam.  On this day the Jew gets in touch with 'what is it that God has in mind for all mankind'? Another theme for this day is the Day of Judgment, causing the individual to be judged for all that was done in the past year, while assessing the potential for the upcoming year. A ram's horn or shofar is blown to call the nation into a time of repentance and spiritual renewal.  It may be considered a 'wake up' call or as a reminder of important points in their history.
 

Yom Kippur 
or
Day of Atonement
or 
Second Day of Awe

10 days after Rosh ha Shonah comes The Day of Atonement.  It's a day of fasting and prayer for past sins.

The first Yom Kippur was for the repentance of the sin of the Golden Calf.  It took 80 days for Moses to convince God to accept the peoples apologies and atonement for that sin.  The very day that the atonement was accepted, was the first Yom Kippur.

The same power of forgiveness as seen on the first Yom Kippur is believed to be felt for all those in true repentance on this day.
 

Rabbinical The 7 Rabbinic Holidays are 5 fast days and 2 celebrations which were created since coming into their promised land of Israel and mandated by the rabbis. Half day fasts are from daybreak to nightfall.  Full day fasts are from nightfall to nightfall.  History plays a very important part in understanding the reason for these holidays.

The Jews were in the land 850 years before being exiled the first time by the Babylonians.  Then they came back for 420 years to be exiled a second time by the Romans.  Now after being exiled for 2000+ years they have been back in their land for the last 50+ years.  During those initial 850 years the Jewish people developed dramatically, building the temple of Solomon in the capital of Jerusalem where both became the focal point for learning.  Unfortunately idolatry became a real snare to the people due to their complacency at the good life. 

Holy day

Information

10th Day of Tevev
Half day fast
 

This fast-
acknowledges loss of temple in Jerusalem when siege was laid.

The very day that the Babylonians laid siege to Israel on the 10th of the month of  Tevev, is when the rabbis declared a fast for half the day.

17th Day of Talmuz
Half day fast
 

This fast-
acknowledges loss of temple in Jerusalem when the walls were breeched.

This was during second Temple period.  History notes this is also the same day the Jews sinned with the golden calf.

Tisha b'Av
9th Day of Av
Full day fast

 

This fast-
acknowledges loss of temple in Jerusalem when the temple was actually destroyed.

Three weeks after the Romans broke into Jerusalem, they destroyed the temple for the second time.  The first was done by the Babylonians.  Historically, this is the day the Jews rejected going into Israel, both temples were destroyed on the 9th of Av, the Jews were expelled from Spain, World War I began, and the first trains to  Austwichz were sent to the death camps.

Fast of Gedaliah
Third day of Tishrai
Day after
Rosh ha Shonah

This fast-
acknowledges how the Jews deal with nations while in exile.

During the 70 year captivity by the Babylonians, a remnant of Jews remained in Israel. They rebelled and assassinated the Govenor Gadaliah, so that day has now been proclaimed as a fast day.

This is recognized as a result of the Jews obstinacy and failure to resign to God's judgment.

Fast of Esther
Half day fast
13th day of Adar
or the day before Purim

This fast-
acknowledges how the Jews deal with nations while in exile.

Jewish Queen Esther of the Persian Empire was used by God to save her people from an annihilation planned by Haman, an evil royal advisor.  Before she went to petition the King, she petitioned her people to go on a 3 day fast.

This rabbinical fast is to remind the people that although they must know how to get along with their neighboring countries, they are to maintain their own principles and way of life and not be too compromising.

Purim
or
Feast of Lots    

During the 70 year captivity by the Babylonians, Persia conquers Babylon and lets the Jews return to Israel to rebuild the temple.  The building was stopped for 18 years however.

Lots had been drawn to decide the dates of an intended massacre of the Jewish people. This day commemorates their deliverance  by a beautiful Jewish girl named Esther who had become Queen of the ancient Persian Empire 'for such a time as this'.

Purim celebrates the 'hidden' miracle, not seeing God exclusively.

Chanukah 
or
Feast of Dedication
or
Feast of Lights 
Chanukah

The Greek culture was very enticing to the Jews at that time and many adapted their ways, becoming Helenists.  The first known religious persecution and martyrdom were a result, with the Greeks goal to wipe out the Jewish culture altogether.

A rebellion was led by a group called called the Macabees, consisting of the High Priest and his band of followers including 5 sons.  They were able to re-conquer the Temple. 

This feast or Jewish holiday commemorates the re-dedication of the Temple in Jerusalem after the Macabee's victory over the Syrians in 165 BC.
It's celebrated for eight days to recognize the miracle of God replenishing 1 days worth of oil into 8 for the lamps of the temple.

Chanukah translated means dedication and it commemorates the 'revealed' miracles.

(Information excerpted from: Crash Course in Jewish Holidays by Rabbi Avraham Goldhar and found free at aish.com)