A watercolour showing a view through the Town Gate, looking westwards down Castle Hill. The Henry VIII Gateway and Salisbury Tower are on the right. In the centre, a couple and child in a horse and gig are proceeding up Castle Hill. A soldier on the left is leaning over the fence of one of the houses, possibly to flirt with a woman at the window, observed by another woman above. Other figures in the background and through the gate are unloading barrels and baskets. A ruler has been used for some of the architecture, and a column of pinpricks is visible at the right edge for the lines of brickwork. The sheet is circumscribed with a black line and white border, and mounted on a yellow, grey and black ink line border of a type associated with works in the collection of Sir Joseph Banks. For other mounts of this type, see RCINs 914547, 914541 and 914538. Inscribed on the verso in pencil, possibly in the artist's hand, 'Windsor. View of the Town through the Gateway, from the Castle Hill', and a queried date of 1768.

There are two pencil drawings of the same view, one in the Royal Collection (RCIN 914544) and one in the Staatliche Museen Greiz (E 458), as well as a related outline etching in the British Museum (1904,0819.590), part of a series dated 1777. These are all probably later than this watercolour. A pencil drawing of the figures in the horse and cart, dated 1768, is also in the Royal Collection (RCIN 914545), and another was formerly with Agnews. Another pencil drawing in the Staatliche Museen Greiz (E 455) shows the view through the gate. A 'Town Gate of Windsor' was exhibited by Paul Sandby at Spring Gardens in 1768 (no. 277); possibly this work or a related bodycolour.

The Town Gate of Windsor Castle was set at right angles to the Henry VIII Gateway and built in the reign of Elizabeth I. In the eighteenth century the main pedestrian route to Datchet was along this road, passing up Castle Hill and into the Little Park. The Gate was taken down between 1832 and 1837.