Rowlandson visited Cuckfield fair in 1789 to make drawings for his book 'An Excursion to Brighthelmstone made in the year 1789'. The volumen was a joint venture with his friend Henry Wigstead (1760 - 1800) and was intended to illustrate their journey to Brighton, then known as Brightelmstone, on the south coast. It was one of a series of illustrated accounts of travels in Britain published during this period.
The accompanying text in the book for this image states that the fair at Cuckfield took place in September and was 'resorted to by a great number of pretty rustic Females and by a multitude of Happy Swains'. The artist's eye for comic incident and his fluid calligraphic line are evident in the treatment of the figures in the scene, who seem to interest him more than the topography of the village. The Church of the Holy Trinity can be seen in the background.