We study how the microscale topography of a solid surface affects the apparent advancing and receding angles at the contact line of a liquid drop pinned to this surface. Photolithographic methods are used to produce continuous circular polymer rings of varying cross-sectional size and shape on hydrophilic silicon wafer surfaces. Drops of water and glycerol are dispensed into the areas bounded by these rings, and critical apparent advancing and receding angles are measured and correlated with the parameters that characterize the ring cross section. For much of the examined parameter space, the apparent critical angles are independent of ring height and width and are determined primarily by the slope of the ring's sidewalls, consistent with a model by Gibbs. For ring heights below a few micrometers, the critical angles decrease below the values predicted by the sidewall slopes alone. These results provide data for calculation of hysteresis on naturally rough surfaces and demonstrate a simple method for controlling and enhancing contact line pinning on solid surfaces. © 2009 American Chemical Society.