Hydrophobicity and wetting transition behavior of water droplets were investigated on microstructured hydrophobic rough surfaces with pillar arrays, fabricated by self-replication with hydrophobic polydimethylsiloxane(PDMS) together with the use of CNC machine. The surfaces consist of microscale pillars(diameter: 105 mm, height: 150 mm) with varying spacing-to-diameter ratio (s=d) ranging from $1:0 to $3:3. A deionized(DI) water droplet of 4.3 ml was placed on hydrophobic surfaces and contact angles(CA) were measured by the digital image processing algorithm. A wetting transition from the Cassie state to the Wenzel state was demonstrated depending on the values of s=d, from $1:81 to $2:95. In the transition regime, a partial penetration of liquid meniscus which moves downward in the groove formed by four pillar posts was observed. It was also found that the contact angle prediction using the Cassie-Baxter equation showed fairly good agreement with experimental data, whereas in the transition regime, the rapid decrease in CA was found.