Large and downed woody fuels remaining behind a wildfire’s flame front tend to burn in a smoldering regime, producing large quantities of toxic gases and particulate emissions, which deteriorates air quality and compromises human health. Smoldering burning rates are affected by fuel type and size, the amount of oxygen reaching the surface, and heat losses to the surroundings. An external wind has the dual effects of bringing fresh oxidizer to the fuel surface and porous interior, while at the same time enhancing convective cooling. In this work, a series of experiments were conducted on single and adjacent poplar dowels to investigate the effect of fuel geometry and wind speed on smoldering of woody fuels, including its burning rate and combustion products. Dowels had variable thickness (19.1 and 25.4 mm), aspect ratios, and arrangement (number of dowels and spacing between them). Using measurement of mass loss, CO, and HC production as indicators of the smoldering intensity, the results indicate that the arrangement of smoldering objects significantly affects burning rates and emissions. Specifically, spacings of 1/8 and 1/4 of the dowel thickness enhanced the smoldering process. The smoldering intensity was also enhanced by increased external wind (ranging between 0.3 m/s and 1.5 m/s), but its effect was dependent upon the spacing between the dowels. The convective losses associated with the spacing were further investigated with a simplified computational model. The simulations show that the wind significantly increases convective losses from the smoldering surfaces, which in turn may offset the increase in smoldering intensity related to the higher oxygen flux at higher wind speeds.