Much of Seago's early 1930s imagery focusses on the bohemian lifestyle of travelers and circus entertainers around the Norfolk countryside. Alongside his friends and patrons, Seago spent time amongst these communities where he captured scenes of touring performances and the everyday life within the campsites. With particular influence from Sir Alfred Munnings and John Constable, Gypsy Caravan shows Seago's skill in landscape and equestrian painting.

This work is thought to have been exhibited at the Sporting Gallery, Norwich during the 1933 exhibition Circus Scenes, Landscapes and Racing. A fragment of the Eastern Daily Press’s review of this exhibition is secured to the canvas overlap.