Weenix was trained by his father, Jan Baptist Weenix, who had certainly spent time in Rome and whose sketches perhaps provided Jan with details such as the columns (apparently from the Temple of Vespasian). Weenix the younger became best known for large still-lifes of dead game, but this early work is in the manner of his father.
The shepherd is usually described as removing fleas from the dog, but he is more likely trimming the puppy's dew-claws. In the background a continuous stream of travellers and merchants is making their way across the landscape. The boy’s care for his dogs and sheep was probably intended as an allegory of industry.