Early sketch books reveal that Helen Allingham visited the village of Whittington in 1873 and again in 1880. However, it was not until the 1890s, and by then a successful artist, that she returned to paint the stone cottages that stood along the main street. The buildings today remain virtually as they were a century ago.
During her visit to Whittington, Allingham stayed at Whittington Court, of which she was to paint both the interior and exterior. The house belonged to Colonel Dobell, a relation of Briton Riviere's wife Mary Alice, both of whom were long standing friends of the artist.