The extended tour that Roberts undertook between August 1838 and July 1839 of the Near East was the fulfilment of 'the dream of his life from boyhood'. He travelled to Egypt, arriving first in Alexandria on 24 September, and spent nearly five months until 7 February travelling through the country, before setting off for the Holy Land, arriving in Jerusalem on 28 March. He only stayed for a couple of days before continuing his travels around the region, visiting Jericho, Jordan and the Dead Sea, before returning for a week to Jerusalem. On his return he embarked upon his monumental five volume publication, The Holy Land, Syria, Idumea, Arabia, Egypt and Nubia, published between 1842 and 1849 with 247 lithographs by Louis Haghe, after Roberts' drawings. The preface to this publication stated that to visit the region and 'make drawings of the scenes of sacred history and the antiquities of Egypt had been, long before this journey was undertaken by Mr Roberts, the brightest of his anticipations as an artist'.
Despite the artist's excitement at visiting Jerusalem, Roberts was deeply disappointed by his stay there. The city had been quarantined for almost a year due to plague and Roberts arrived the day the barriers were lifted and the city re-opened. As a result conditions in the city were miserable and he wrote in his diary, 'surely there cannot be any city more wretched. How has the mighty fallen!' He continued in another entry 'The city within the walls may be called a desert, two thirds of it being a mass of ruins and cornfields: the remaining third...being such a paltry and contemptible character that no artist could render them interesting'. Despite this disappointment, Roberts made numerous drawings of the city and its surroundings from which he then worked up into finished watercolours and oils on his return to England.
When his volumes of prints were published they caused an immediate sensation as they provided the British public with the earliest visual records of the region, and over two thousand copies were sold before the publication date. The present watercolour was executed in 1841 as part of the series of watercolours that Haghe worked from to create the lithographs for The Holy Land. This work was reproduced as plate 23 in Volume I of the series. It shows the ancient entrance to the Citadel or Tower of David, located on the western side of the old city. It is the highest point of the south western hill of Jerusalem and as such overlooks the entire city. The Holy Sepulchre can be seen to the right of the composition.