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This picture is one of the most beautiful and powerful landscapes painted by Gainsborough during his final years in Bath, combining bucolic cattle, idyllic pastoral lovers, and a distant golden landscape. The composition is consciously Claudean, and the handling bold, with slabs of impasto in the sky. It is thought to have been painted at Shockerwick Manor, the home of the prosperous Bath carrier Walter Wiltshire (c. 1719–99). Gainsborough was a frequent visitor and he used Wiltshire's regular ‘flying waggon’ service to transport his paintings to London for exhibition.

Gainsborough gave Wiltshire this work, together with The Harvest Waggon, when he left Bath for London in 1774. The latter dates from 1767, and Rocky Wooded Landscape with Rustic Lovers, Herdsman and Cows appears to have been painted as a pendant to it, either in 1771, or shortly before the artist’s departure for London. Both pictures were sold by John Wiltshire in 1867. They remained together until 1946, when The Harvest Waggon was acquired by the Barber Institute, Birmingham, and Rocky Wooded Landscape with Rustic Lovers, Herdsman and Cows was bought by the newspaper proprietor Lord Camrose.