A watercolour drawing of Winchester Tower, Windsor Castle, showing a view of the Hundred Steps, an ancient route from Thames Street to the Canons' Cloister. In the foreground a man in a blue coat and tricorne hat holding a cane is resting against the banister. Seated on the step is a boy eating a biscuit, with a dog climbing on his lap. The boy's hat is discarded on the steps. Further back a young man and a girl are descending the steps, one leaning over the balcony figure hinting at the dramatic view from the north side of the Castle. The man at the top with a heavy load is preparing himself for his descent. In the background is Winchester Tower. Trees on the left and right. Inscribed on the verso in pencil, possibly by the artist, 'Windsor. View of the Winchester Tower and part of the Hundred Steps'. The sheet of paper has a grey line and grey wash border. With a black ink bordered mount.

The 'Hundred Steps' provided pedestrian access from the town to the north side of the Lower Ward from the medieval period. Beginning at a gatehouse on Thames Street, the steps emerge into the Canon's cloister. They were rebuilt in the nineteenth century and are no longer open to the public. Sandby made several drawings of the steps, populated with townsfolk making use of the pathway. A bodycolour of the same view, with different figures, is in the Castle Museum, Nottingham. The same subject, drawn from the bottom of the steps, is seen in RCINs 451578, 914572, 914571, a bodycolour in the National Gallery of Ireland, Dublin, and a pencil drawing in the Staatliche Museen Greiz (E 482). An etching of the same view is in the British Museum (1904,0819.583), part of a set of Windsor views dated 1780. Paul Sandby made many drawings and watercolours of Windsor Castle during the second half of the eighteenth century.