The stations on the two pilgrimage routes of the ʿAbbasid Age from ʿIrāq to the Hijāz – one route taking off into the Arabian steppe from Kūfah and the other from Basrah – are plotted out in Spruner-Menke Hand-Atlas für die Geschichte des Mittelalters und der Neueren Zeit, 3rd. ed. (Gotha 1880, Perthes), Map 81.
Here is that map: the two long, lonely roads with their stations and wells are clearly marked.
Kufa was an Arab cantonment on the border between the Arabian desert and Iraq. The fourth of the Rightly-Guided Caliphs, Ali, had moved his capital there from Medina in order to confront Muawiya, the governor of Syria, in battle at Siffin on the Upper Euphrates (657). This was the end of the great age of Medina which had begun in 622 with the Hijra. Ali was later assassinated (661).
Muawiya persuaded his son, Hasan, to renounce rights to the Caliphate. Ali had been the son-in-law and cousin of Muhammad. Shia Muslims believe that the succession should have continued through him. Kufa is one of their holy cities in Iraq, along with Kadhimiya, Karbala, Najaf, Samarra.
Muawiya (Muhammad had married his sister, but he was not otherwise closely related to the Prophet), established the Umayyad dynasty in Damascus.
The Abbasid caliphs moved the capital to Baghdad after overthrowing the Umayyads everywhere except in Iberia (al-Andalus), where they survived, until 1031, in the Caliphate of Cordoba.
Basra had been founded by the second Rightly-Guided Caliph, Umar, while confronting the Sasanids.
A more northerly route from the Euphrates to Damascus and then south, “the King’s Highway”, is described here (old post). At the Gulf of Aqaba, the Highway would branch westwards across Sinai and south-eastwards into Arabia.
The road from Damascus to the Hejaz and beyond to Yemen was an ancient one.
Muhammad himself conducted caravans from Mecca to Damascus and back as the employee of his future wife, Khadijah. The most probable dates of his journeys [into Roman territory] are the peace-years between 591 and 604.
“Until the 19th century there were three main caravans to Mecca. The Egyptian caravan set out from Cairo, crossed the Sinai Peninsula and then followed the coastal plain of western Arabia to Mecca, a journey which took from 35 to 40 days. It included pilgrims from North Africa, who crossed the deserts of Libya and joined the caravan in Cairo. The other great caravan assembled in Damascus, Syria, and moved south via Medina, reaching Mecca in about 30 days. After the capture of Constantinople by the Ottoman Turks in 1453, this caravan began in Istanbul, gathered pilgrims from throughout Asia Minor along the way, and then proceeded to Mecca from Damascus. The third major caravan crossed the Peninsula from Baghdad.”
The Baghdad caravan went via Kufa. The Hejaz Railway (map), part of the Ottoman railway network, followed the route of the Damascus caravan and was an extension of the line from the Haydarpaşa Terminal in Istanbul (Asian side) beyond Damascus. Work began in 1900 under Abdul Hamid II, with German help. The intention was to go as far as Mecca. The line reached Medina on September 1 1908, the anniversary of the Sultan’s accession, but had got no further than this – four hundred kilometres short of its goal – when war broke out. In 1913 the Hejaz Railway Station was opened in central Damascus. There was a branch line to Haifa.
The Emir Hussein bin Ali, the Sharif of Mecca, viewed it as a threat to the Arabs, since it provided the Turks with easy access to their garrisons in the Hejaz, Asir and Yemen. A section of it was blown up by TE Lawrence during the Arab Revolt. After the fall of the Empire the railway did not reopen south of the Jordanian-Saudi Arabian border. There is talk of reopening it now.
The Berlin to Baghdad Railway (post here) was being built at the same time. It, too, was incomplete in 1914.
A Study of History, Vol VII, OUP, 1954 (footnote)
Mankind and Mother Earth, OUP, 1976, posthumous