<p>Urbanization transforms landscapes and may alter background matching for polymorphic species that rely on cryptic coloration for survival, potentially generating urban–rural clines in traits related to coloration. Such clines are evident in eastern gray squirrel (<i>Sciurus carolinensis</i>) populations, for which a melanic morph is currently more prevalent in cities but was historically more prevalent in rural woodlands prior to urbanization. We compared the degree of crypsis between the two primary color morphs of gray squirrels – gray and melanic – among the suite of habitats that predominate along an urbanization gradient to test whether an altered visual environment may contribute to the maintenance of an urban–rural cline in morph prevalence. Detectability of taxidermy mounts of each morph against their backgrounds in replicate sites within each habitat was quantified with human observers and image pixel classification. The melanic morph was more conspicuous than the gray morph in all habitat types and across seasons, as evidenced by greater detection probabilities by human observers and lower background matching. Coat color in gray squirrels likely mediates visual detection by predators, potentially resulting in selection against the more conspicuous, melanic morph in rural woodlands where predation is the primary constraint on survival. The greater conspicuity of the melanic morph on road surfaces may be beneficial in cities where vehicular collisions are the primary cause of squirrel mortality. We conclude that differential crypsis between color morphs across the habitat continuum of urban–rural gradients may play an important role in maintaining urban–rural clines in coat color in eastern gray squirrels.</p>