The City of Jasmine.
"Oldest continuously inhabited city in the world."
It was founded in the 3rd millennium BCE and (according to the Unesco World Heritage site) "has some 125 monuments from different periods in its history."
When Imad al-Din Zengi, the Prince of Mosul, laid siege to Damascus in 1138, Damascus resisted by allying with the Crusader Kingdom of Jerusalem (ruled at the time by Fulk V of Anjou [1089-1143]). The admirably tolerant Seljuq-Christian alliance turned back their common enemy. It was this conflict that prompted Raymond of Poitiers, Prince of Antioch, to send Bishop Hugh of Jabala to Pope Eugene III for aid. It was Hugh at the court of Pope Eugene whose mention of a Nestorian priest-king in the East started the legend of Prester John.
Saladin, the noble foe of Richard Lionheart, founded the Ayyubid dynasty, Muslim Kurds who ruled an independent Damascus. Saladin allowed pilgrimages to Jerusalem, with the understanding that the Crusaders would return home after fulfilling their Crusading vows. After Saladin's death in 1193, Damascus was ruled sometimes by Ayyubids from Damascus, sometimes by Ayyubids from Cairo.
By this time, Damascus was one of the western endpoints of the Silk Road. Damascus itself was known for crafts and cloth, and the cloth called damask was a specialty.
Independent Ayyubid rule ended in 1260 with a Mongol Invasion; when the Mongols left, Damascus was reduced to being a provincial capital of the Mamluk Empire of Egypt. A few generations later, the Black Death killed up to 50% of the population.