The uropygial gland and the oils it produces have been shown to serve important functions in many bird species including plumage maintenance and chemical communication. Previous species comparisons of uropygial gland size have only been conducted in South American and European birds and have found little to no phylogenetic signal. Here, we document uropygial gland measurements of 34 different passerines, 1 hybrid chickadee population, and 1 Piciformes in eastern Pennsylvania, most of which are reported for the first time. Uropygial gland size is positively related to overall body size, controlling for phylogenetic relatedness. We show a significant phylogenetic signal of relative uropygial gland size and many of the species with the largest gland sizes belong to the Paridae. Overall, females show a nonsignificant but slight trend of larger relative uropygial gland sizes than males. This effect is stronger in some species than others and can also be seasonally dependent. We found no effect of relative total eggshell surface area or nest location on relative uropygial gland size. Together our results provide the first documentation of uropygial gland sizes in many of these North American species and provide interesting insight into factors influencing relative gland size including sex, season, and species.