Plane contact problems of an elastic, homogeneous, and isotropic layer supported by a Winkler foundation are studied in this paper. The elastic layer has a finite depth and infinite in-plane dimensions. The upper surface of the layer is in plane contact with a rigid indenter. The particular applications studied in this paper are formulated by first providing the solution for a line load. For the case of a rigid cylinder, the upper portion of the load deflection response is modeled using beam theory with wrapping. The contact pressure distributions for the relatively flexible foundation cases can be accurately determined from the wrapping theory.