Superhydrophobic surfaces are characterized by their peculiarities, such as water-repellent, anti-icing, and freezing-delay properties. Wetting dynamics of deposited water drops on cooling hydrophobic surfaces, which directly affects the aforementioned properties, has not been studied thoroughly. Here, water drops are cooled on different hydrophobic surfaces in a controlled environment. During the cooling process, a significant increase in the drop footprint and decrease in the apparent contact angle are observed because of premature and capillary condensation, followed by thin water film formation adjacent to the solid-liquid-gas line. The water thin film propagates on the hydrophobic substrates radially away from the trijunction, followed by spreading of the drop on the film, which was experimentally validated through high-speed visualization. In addition, the roles of physical variables, such as the substrate temperature, humidity of surrounding air, types of hydrophobic surfaces, surface roughness, and drop volume, on post-spreading shape are investigated experimentally.