Commenting on Romantic ruin painting, Louis Hawes states that medieval ruins were popular subjects for topographical artists and watercolorists. Indeed, the portfolios of Samuel Prout and Samuel and Nathaniel Buck—trained topographers of the Romantic era—all include medieval ruins. Hawes further observes that artists of architectural decay also tend to position their ruins in the middle ground (462). This again is true of several of the aquatints based on William Gilpin’s picturesque drawing of ruins—for example, the ruins of Castle Abergavenny (William Gilpin, Observations on the River Wye... 1792. Plate 12). The London topographer George S. Shepherd fits the first characterization, but not the second. His Dover Castle recedes into the background, and the castle, the hill, and the road (slightly more pink) are all colored with the same wash.

Hawes remarks that the 1830s was a period of decline for the Romantic ruin (457). Dover Castle from a Market Stall may support this assertion in that, despite the title of the painting, the castle is not the sole focus of the scene. Shepherd began his career as topographical draftsman and became a talented renderer of urban architecture, particularly of London as seen in his sketches in J. Booth's Architectural Series of London Churches (1818) and Robert Wilkinson's Londina illustrata (1825–34). At East Acton (1814) and his scenes on the River Thames (ca. 1818–25) display his abilities as a rural and natural landscape artist (Peltz). In this light, Dover Castle seems to be a hybrid metropolitan and natural landscape scene: the interaction between a customer and distracted attendant in a small-town market scene complements the historic, medieval castle that appears almost transformed into a natural land formation.

Some scholars of the Romantic period, such as Malcolm Andrews and Anne Janowitz, assert that landscapes and ruined architecture aroused historical memory and became emblematic of national identity in the late eighteenth and nineteenth century. Several primary sources support this opinion. A ruined mansion in Brambletye was the occasion for John Byng to contrast his own era to "those Gothic days":

Over and about these ruins I . . . meditated . . . [on] the great improvements of the roads, which have introduced learning and the arts into the country and removed the (formerly wretched) families, who buried themselves in mud and ignorance, to the gay participation of wit and gallantry in the parishes [towns] of Marylebone and St. James! (89)

Commenting on the ruined Caraig-cennin Castle in Wales, traveler Henry Penruddocke Wyndham declared: "'This was doubtless . . . a British building, as is evident from its plan and the style of its architecture’" (quoted in Mavor 343). Furthermore, the picturesque aesthetic glorified decayed structures from the medieval period because they had been subsumed by the land, stained, overrun and rent by insects and vegetation (Ruskin qtd. in Lowenthal 157). While Dover Castle is not clearly depicted as a ruin, this perspective of Dover Castle emphasizes the union of architecture with land, a source of historic pride wholly integrated into English soil.

A woman in a black cloak with a young bonneted girl behind her stands in a covered, open-air market filled with baskets of fruits and fresh goods. The woman grips a large basket of grapes and looks toward someone who appears to be a young boy. This short figure, perhaps the store attendant—in a beige coat, black beret and brown boots—has turned his back to the viewer. A dirt road flanked on both sides by one-story homes runs from the back of the market into the distance. Two figures (difficult to see as they are faded in the watercolor) wear top hats and ride down the road in a black carriage. In the far background above the line of residences, a castle sits on a broad hill. Its grounds are extensive and cover the entire breadth of the hill. A crenellated tower with a white flag stands in the middle of the castle complex. In this image, the centrality of Dover Castle and its integration into the surrounding landscape demonstrates the centrality of medieval structures in constructing national identity during the Romantic era.