Jewish Pilgrimage in 16th Century Jerusalem
There also isn't as much about pilgrimage to Jerusalem and Hebron as I'd hoped, except that it existed. Jewish pilgrims coming through Damascus had to pay a tax at Nablus, where they were given a receipt which allowed them entry to the city. The tax revenue was forwarded to Jerusalem for keeping up its defenses. The main pilgrimage season was the Passover/Shavu'ot period, and while Cohen didn't mention the Wall, I see no evidence that anything was forbidden, and in another chapter he mentioned a concentration of Jews living near it.
There was, however, a surprising amount of information about pilgrimage to Samuel's tomb. Going to that site required payment of a special tax, though a very small one, and while there was no special time for it, it was often an add-on to pilgrimages to Jerusalem. The site, however, was often a source of conflict. First, right after the Ottoman conquest in 1517, Karaites tried to ban other Jews from the synagogue, and relented only after a decree from the Ottoman authorities. There was also conflict with Muslims in the area. In the 1530's, Muslim villagers in the area complained that the Jews were unduly boisterous when they returned from the site, though the government took no action. In 1550, there were complaints that the Jews camped at the site for long periods and their pack animals invaded property in the area. The qadi ordered the Jews to keep track of their pack animals. In 1554 and 1555, there were major attempts to disrupt the pilgrimage, and local Muslims seized the shrine and tried to turn it into a mosque. The matter went all the way to Istanbul, which ruled in favor of Jewish rights. Something similar happened in 1598, and that time the official government ruling was buttressed by a fatwa.
I suspect the matters related to Samuel's tomb show the true story of intercommunal relations during the period. Most Muslims probably had nothing against a Jewish pilgrimage. When the pilgrimage became associated with noisy celebrations and animals getting into your fields, however, you started opposing it and complaining about "those Jews." Considering Cohen's book was based on Ottoman legal documents, the relative lack of information and Jerusalem and Hebron probably means things went smoothly.