Constable made a small pencil sketch of Hadleigh Castle near Southend in Essex in 1814, on his only visit to the area, when he wrote to his future wife Maria: 'At Hadleigh there is a ruin of a castle which from its situation is a really fine place - it commands a view of the Kent hills, the Nore and North Foreland & looking many miles to sea' (letter of 3 July 1814; in R.B. Beckett, ed., John Constable's Correspondence, II, Ipswich 1964, p.127). He returned to the pencil sketch fifteen years later, to develop the six-foot painting. He made a small preparatory oil sketch, probably in 1828 (Paul Mellon Collection, Upperville, Virginia), based on the drawing, but with the addition of a shepherd and his flock at the bottom left. In a pen and ink drawing made at around the same time (collection David Thomson), the composition has become decidedly more horizontal, having been extended on the right to include the distant Kent shore. A dog has replaced the shepherd's flock, and a tree has been added beside the castle's left-hand tower. The Tate's large oil sketch introduces cows in the middle-distance and gulls flying above the sea.
Constable's wife Maria died in November 1828, and the sombre, desolate tone of the work is generally assumed to reflect his mood at this time. In a letter of 19 December of that year, he wrote to his brother Golding: 'I shall never feel again as I have felt, the face of the World is totally changed to me' (in C.R. Leslie, ed. Hon. Andrew Shirley, Memoirs of the Life of John Constable, R.A., London 1937, p.234).
Leslie Parris and Ian Fleming-Williams, Constable, exhibition catalogue, Tate Gallery, London 1991, pp.243, 312-14, 355, reproduced in colour p.313