A watercolour drawing of the Henry VIII Gateway, looking into the Castle from the gate towards the west end of St George's Chapel and the Horseshoe Cloister. Several groups of figures are standing in the gateway. A woman with a water cart and two small mules is led by a man carrying a bucket; two soldiers are on duty near their guardbox on the left, one leaning on the wall next to a small boy with a jug and a dog or goat. On the right, a chimney sweep is standing with a small boy, and two well-dressed ladies behind. At the far right, a knife-grinder is working at his stall. In the background, through the gateway, an elegant carriage has just entered the Castle. The sheet is mounted on a yellow and grey wash line bordered mount of a type associated with drawings acquired at the Paul Sandby estate sale in 1811. Inscribed on the mount in faint pencil, possibly in the artist's hand, 'Town Gate Windsor Castle'.

The costume of the two elegant ladies under the gateway suggests a date of about 1775 or later. An engraving of the same view was included in Sandby's '150 Select Views', published 1780. A bodycolour of the same view with many of the same figures is at the Museum of New Zealand Te Papa Tongarewa, Wellington. A watercolour drawing of the Henry VIII Gateway from inside the Castle looking out to the town is in the Royal Collection (RCIN 914550). As with this drawing, there is a related bodycolour version of the same subject (Courtauld Gallery, Spooner Bequest, D.1967.WS.85). Both bodycolours are dated 1767 and were possibly intended as a pair. At the Society of Artists in 1763 Sandby exhibited 'A gateway in Windsor Castle', and another 'Town Gate, Windsor Castle' in 1768.