This dataset comprises an extensive series of experiments conducted in a large boundary layer wind tunnel (BLWT) to investigate the effects of upwind terrain on surface pressures acting on a low-rise building. Three geometrically scaled models of the Wind Engineering Research Field Laboratory (WERFL) building were immersed in 33 boundary layer flows through precise adjustment of an automated roughness element grid called the Terraformer. The roughness configuration of the Terraformer was modulated to simulate a variety of upwind terrains ranging from marine to dense suburban. Simultaneous pressure measurements were collected on the surfaces of three models of the WERFL building with geometric scales of 1:20, 1:30, and 1:50. For each model, surface pressures were obtained for three wind directions (0, 45, and 90 degrees), 16 roughness element heights, and two element orientations (wide and narrow edge windward).