Latrun is the first of the hilly ridges that a traveller will see on his way while ascending to Jerusalem, and therefore is of significant strategic value. It was often the site of battles.
In the Bible, Ayalon Valley was the site of a battle in which Joshua defeated the Amorites; during the Crusades, Latrun was also the scene of many attacks. A crusader stronghold there, "Le toron des chevaliers" (The Tower of the Knights), may be the origin of the name "Latrun". The other theory is that the name orginates from the name the Christian pilgrims gave to the town "Castellum bonu Latronis" (The Fortress of the Good Thief).
In the 1861, a monastery was established in Latrun by French monks of the Trappist order. The monks there make a living in producing liquor, although their order's rules imply observance, and in particular abstinence from alcohol. In the areas surrounding their monastery, the monks grew vines.
Following the Great Arab Uprising 1936-1939, the British authorities built a number of police forts of similar design (named Taggarts after their constructor) in various locations; Latrun was chosen as such a site due to its strategic significance, particularly its dominant position above the old Tel-Aviv-Jerusalem highway passing immediately below the hill-line. That police fort had an enormous impact on the outcome of the 1948 Arab-Israeli war. As the last British troops departed from Palestine in May 14, 1948, the fort was overtaken by the Jordanian Arab Legion.
Just 10 days after the declaration of Israel, on May 24, 1948, the fort was assaulted by combined forces of Israel's newly-created 7th Brigade, and a battalion of the Alexandroni Brigade (where Ariel Sharon served as a platoon commander; he was wounded with most of his platoon and later recalled the decision to retreat to a nearby vale as the most crucial tactical decision of his life). The attack (codenamed "Bin-Nun A") failed, with heavy casualties. A week later, on June 1st, the fort withstood yet another attack ("Bin-Nun B"), even though its outer defences were breached.
The fort was used to shell Israeli traffic on the highway and thus effectively impose a siege upon Jerusalem. During early June, an alternative route was developed that was nicknamed the "Burma Road" after the American and British route into Japanese-controlled China during World War II.
Many of the Israeli conscripts have just survived the Holocaust and were new immigrants; most were poorly trained. The equipment was also very poor, and artillery support was lacking. The results of the battle were mixed. The official combined number of casualties for both the battles was 139 (an extremely high figure for an assault conducted mainly by two battalions). As records are carefully kept for each fallen soldier, this figure seems exact. While the Tel-Aviv Jerusalem highway was not secured, the two Battles of Latrun can be seen as a limited strategic success, since they contained the Legion and allowed the opening of the bypass road, which lifted the siege from Jerusalem.
The battle, however, is often brought up as a failure of much greater proportions than it was; for instance, in 1985 Member of Knesset Uzi Landau has claimed that 2000 soldiers died in the fighting (which would make up a third of all Israeli casualties of the 1948 war!). When reminded about the real casualty count, Landau agreed to lower his estimate to 1000.
In the 1949 cease-fire agreement, the fort remained a bulge under Jordanian control; a bypass road was built, but Latrun was still only several miles to the east from Israel's only international airport. In 1967, Latrun was captured by Israeli forces. The fort has since become a museum and a memorial site for Israel's armored forces, whereas the monastery is considered a popular tourist attraction.
The 190 Christian Arab inhabitants were also ethnically cleansed in the process, see Palestine Remembered.