From the dawn of the history of Jerusalem the Mount of Olives served the city's inhabitants as a place of burial.  The fact that it is made of soft chalk - an easy-to-hew rock - and its proximity to the city, turned it into the favoured place for burying the dead already in the 16th century BCE. This tradition of burial was to last for many centuries. The chalk rock is also suitable for growing olive tress and it would seem that already in ancient times olives trees were grown here, and from them the hill received its name.  The Midrash relates the dove took the olive leaf that it brought to Noah after the Flood - from the Mount of Olives.

The Mount of Olives range of hills is the border between the inhabited land and the desert, which, from Jerusalem's earliest days, served as a natural barrier for anyone approaching the city from the east.
The summit of the Mount, which the Bible refers to as its 'head', had, it seems, a special religious significance. It was here that David prayed when escaping from his rebellious son, Absalom:
"And David went up by the ascent of the Mount of Olives, and wept as he went up; and he had his head covered..when David was come to the top of the ascent, where God was wont to be worshipped.." (II Sam. 15:30, 32)
King Solomon, whose "wives turned away his heart after other gods", built 'high places' (cultic sites) for idol worship on these same hills:
"Then did Solomon build a high place for Chemosh the detestation of Moab, in the Mount that is before Jerusalem, and for Molech the detestation of the children of Ammon". (I Kings 11:7)
The exact location of these 'high places' can be learned from the demolition activities performed by King Josiah when he purified the country of foreign worship many years later:
And the high places that were before Jerusalem, which were on the right hand of the Mount of Corruption, which Solomon the king of Israel had built … did the king defile". (II Kings 23:13)
The Mount of Corruption mentioned in the verse, is almost certainly a pejorative nickname for the Mount of Olives, which, in the Hebrew is similar sounding to another name of the hill, the Mount of Anointment, which appears later and is used by the Rabbis of the time of the Mishna.

In the course of the First Temple Period the people of Jerusalem buried their dead on the slopes of the Mount of Olives. Today we know of at least 51 graves from this period. Among them is a grave found on the northern edge of the village of Silwan, of one of King Solomon's foreign wives that is called 'the Grave of Pharaoh's Daughter', apparently on account of its Egyptian style, and a grave bearing the inscription: 'This is [the grave of…]iah, who is over the house'. This tomb is usually identified with the grave of Shebna who was over (in charge of) the house of King Hezekiah of Judah (Isaiah 22:15-16), who carved a tombstone for himself while he was still alive and in so doing incurred the wrath of the prophet: "What hast thou here, and whom hast thou here, that thou hast hewed thee out here a sepulchre?" (Isaiah 22:16).
In describing the withdrawal of the Divine Spirit from the First Temple prior to its destruction, the prophet Ezekiel says that after leaving the city, it hovered over the Mount of Olives: "And the glory of the LORD went up from the midst of the city, and stood upon the mountain which is on the east side of the city" (Eze. 11:23). This verse is the basis of the Midrash that describes the wanderings of the Divine Spirit on leaving Jerusalem and its waiting for three years on the Mount of Olives for Israel to repent its sins. But when this does not happen it takes off into the desert and then to heaven. The prophet Zechariah foresees the return of the Divine Spirit at the end of days to the same place from which it left: "And His feet shall stand in that day upon the Mount of Olives, which is before Jerusalem on the east" (Zac. 14:4).

The focus of Jewish Life in Temple times was Mount Moriah, but the adjacent Mount of Olives was also of great significance. We learn from the sources that in Second Temple times the Mount of Olives became an integral part of Jewish worship in Jerusalem.
The kohen (priest) would go out to the Mount of Olives to burn the Red Heifer. According to the Mishna, the kohen and his retinue would leave the Temple Mount via the Shushan Gate in the eastern wall, and would cross the Kidron Valley on a road built for this purpose to reach the Mount of Olives where the kohen would burn the Red Heifer. 
The summit of the Mount of Olives was the first station in the chain of bonfires that was lit to signal the arrival of a new month. The announcement determining the new month was issued by the Sanhedrin, that sat on the Temple Mount, and the Mount of Olives served as the link connecting Jerusalem with the rest of the country, and over the Jordan River to the east with those Jews who were still living in exile in Babylon.
Moreover, there were places on the Mount of Olives that were used in connection with Temple worship.  There were shops on the Mount where Jewish pilgrims, or women who had given birth and had to make a sacrifice, could buy young doves to take to the Temple.
On the eastern slope of the Mount of Olives there were two villages in Second Temple times: Betpage and Bethany that were used, it seems, for accommodating visitors on pilgrimage to the city. 
As in earlier periods, in the Second Temple Period too, the Mount of Olives served as a place for burying the dead of the city of Jerusalem. During this period there were many burial caves scattered among the gardens and the olive groves on the Mount. Out of these only a few tens of caves have survived or been found. The most magnificent tombstones of this period are the giant monuments carved in the rock of the Kidron Valley: the Tomb of Zechariah's Tomb, the Tomb of Bene Hezir, the Absalom Monument and Jehoshaphat's Cave. The size and splendour of these memorials testify to the fact that important personages of the city of Jerusalem in the Second Temple Period were buried here. On one of the gravestones an inscription is engraved indicating that this burial cave belongs to the Hezir family, one of the priestly families of Jerusalem.
The Roman siege of Jerusalem was conducted from the heights of the Mount of Olives, which was even fortified for this purpose. The Roman Army camp was on the Mount of Olives and its main attack came from this direction. The Roman Legion built a fort on the Mount of Olives and it was here that its permanent camp was located even after Titus camped his army opposite the city walls. It is thought that it was during this period that the wood and the trees on the Mount of Olives and its vicinity disappeared due to the Roman Legions who felled the trees for fortification purposes.

After the Bar Kochba Revolt, Jews were forbidden by one of Hadrian's edicts from living in Jerusalem at all, or in any place from which Jerusalem could be seen, which included, of course, the Mount of Olives. However, once a year, perhaps during the traditional period of mourning for the Temple, the three weeks between the fast days of the 17th of Tammuz and the 9th of Av, many Jews from the Diaspora would make the pilgrimage to Jerusalem, and for money could 'buy the right', as Hieronymus (Jerome) wrote 'to weep for their city and their destroyed Temple'.
When Christian Byzantium took over from heathen Rome, the Christians began to mark those sites in Jerusalem to which they attributed events of the early days of Christianity and erected churches on them. The fact that Jewish tradition held that certain places on the Mount were holy to Judaism (due to David's praying there, the burning of the Red Heifer there, and tradition relating to the Divine Spirit resting there) also brought Christianity to set up places of worship of its own there. In the course of the Byzantine Period Jewish cemeteries on the Mount of Olives were used as places of seclusion and burial by Christian hermits and monks.

With the Muslim conquest of the country the prohibition of Jews living in Jerusalem was lifted and many Jews arrived and renewed Jewish settlement of the city. In the same way the pilgrimage of Jews to Jerusalem was renewed and in this the Mount of Olives played a major role. For a period of hundreds of years starting from the 9th century, when Jews were forbidden to go up to the Temple Mount, ceremonies of Jewish pilgrims took place on the summit of the Mount of Olives. These ceremonies, which usually took place on Hoshanna Rabba, included parades of throngs of people, and the head of the Gaon Yaacov Yeshiva, and kohanim (priests) in spectacular costume. The summit was reached by one of two routes and prayers and liturgical poems were recited around a huge rock on the summit (known as 'the Head Stone' or 'the Cantors' Seat').  This was an occasion where heads of Yeshivas (Talmudic Academies) were appointed, where the calendar was fixed and given to the representatives of the communities, and it was here that the ban against the Karaites was declared. Account of its status at this time, the Mount of Olives was called "the Footstool of Our God", and the declarations of the head of the Yeshiva were known as the "Mount of Olives' Declarations".

The Jewish settlement in Jerusalem was badly affected by the arrival of the Crusaders, and, it would seem, this ceremony ceased to take place, but Jewish pilgrims did not cease coming to the Mount of Olives as individuals. The festive, mass ceremonies of the pilgrims were not renewed even after the country was reconquered by the Muslims, but starting in the 15th century the Zechariah's Tomb began to be a place of pilgrimage and mourning ceremonies for the destruction of the Temple took place there on Tisha B'Av. 
On the western slope of the Mount of Olives, from the bed of the Kidron Valley upwards, the Jewish cemetery continued growing, centuries after the Jews of Jerusalem from the First and Second Temple Periods had been buried there.

Towards the middle of the 20th century the Mount of Olives was the subject of great interest by the European powers. In addition to other things, the Germans constructed the Augusta Victoria complex, and the French built the complex on the southern summit of the hill. The British High Commissioner lived in the Augusta Victoria building and under the British Mandate the Hebrew University was established on Mount Scopus, the northern summit of the Mount of Olives range. Apart from this academic institution, the Hadassah Hospital was also built on Mount Scopus and served all the people of the area, Jews and non-Jews.  In Nissan 5708 (April 13, 1948) a convoy of doctors and nurses went up to the hospital. In a bend in the road in the neighbourhood of Sheikh Jarrah it was attacked and 78 of its passengers were murdered. The British did not bother to provide assistance until after the massacre, and there are, to this day, people still missing as a result of the attack. The Jewish Cemetery, that began close to the bed of the Kidron Valley, continued its climb up the slopes of the Mount of Olives and even wrapped itself around its summit.

For 19 years the Mount of Olives was under Jordanian rule. During those years the University on Mount Scopus was cut off from Jewish Jerusalem. Under the armistice agreement with the Jordanians, only a force of 'policemen' was allowed to go up to Mount Scopus once every two weeks. The force defended the Mount and looked after the facilities there. The academic institution itself moved to a new campus, at Givat Ramat, and to various buildings in the west of the city, and the hospital moved to a new building to the west of the Ein Karem neighbourhood. The cemetery on the Mount of Olives was left without supervision and with no possibility of it being used for burials. In the absence of proper maintenance, but primarily due to deliberate desecration of the graves, the condition of the cemetery deteriorated. Tombstones were damaged and smashed and the area became full of dirt and garbage.
But worse than this, was the deliberate destruction by the Jordanian authorities.
A number of roads were widened, including the main Jerusalem-Jericho road, and graves and gravestones were paved over. Tombstones were taken from the cemetery to be used in building private houses. Blocks of graves on the slope to the west of the road and on the top of the hill close to the "Cave of the Prophets" were deliberately demolished.
The Jordanians allowed a British delegation to conduct an archaeological excavation in the area of the monuments in the bed of the Kidron Valley, around the Absalom Monument and Zechariah's Tomb. The authorization also included a comprehensive permit allowing the rough removal of tombstones and anything buried beneath them.

The capture of the Mount of Olives in the Six Day War enabled the liberation of the Old City and the unification of Jerusalem. The shelling along the "Urban Line" and the fear of a Jordanian takeover of the enclave on Mount Scopus, brought Israel to take swift action.
In the course of liberating Jerusalem, Reserve Brigade 55 reached the Rockefeller Museum complex. A force of jeeps was sent to the top of the Mount of Olives but took a wrong turn and found themselves going down the Jericho road, parallel to the eastern wall of the old city. The force was seen by Jordanian troops on the city wall and came under very heavy fire. The force that was sent to rescue the wounded also came under fire.  Two tanks from Regiment 182 that were sent to help with the rescue were put out of action: one blew up and the other fell into the bed of the wadi. There were many casualties on the slopes of the wadi bed and it took time until they could be relieved.  Despite the error and the casualties, the force reached the summit of the Mount of Olives and from the esplanade of the Intercontinental Hotel (today the Seven Arches Hotel) Gen. Motta Gur directed the battle for the liberation and unification of Jerusalem.  The force went down the Mount of Olives along two separate routes, joining up at the Lions' Gate through which the troops entered the Old City and reached the Temple Mount.