Walking stability is an important factor that is related to working accidents at height. The understanding of the relationship between walking stability and walking conditions remains an unmet need. Therefore, this study aimed to investigate the effect of path height, width, and asymmetric conditions on the pressure and time information of the foot-ground interaction during walking. 12 subjects were required to walk at two height, three width, and asymmetric conditions. Plantar pressures during walking were measured with the F-scan insole sensors. The total pressures were normalized with body weight, and the temporal parameters were normalized with stance time. When the walking height increased, the plantar pressure at the “heel strike” phase did not change significantly, while that at “heel rise” and “toe off” phases significantly increased, and the “heel rise” occurred earlier, indicating a greater foot-ground interaction at the forefoot part of the sole. As the path width increased from 0.6 m to 1.2 m, the foot-ground interaction as well as the asymmetric effect approached to that of overground walking. The findings could help improve the risk assessment and footwear design.