Superhydrophobic surfaces have considerable technological potential for various applications due to their extreme water repellent properties. The superhydrophobic surfaces may be generated by the use of hydrophobic coating, roughness and air pockets between solid and liquid. The geometric effects and dynamic effects, such as surface waves, can destroy the composite solid-air-liquid interface. The relationship between the water droplet size and geometric parameters governs the creation of composite interface and affects transition from solid-liquid interface to composite interface. Therefore, it is necessary to study the effect of droplets of various sizes. We have studied the effect of droplet size on contact angle by evaporation using droplets with radii ranging from about 300 to 700 microm. Experimental and theoretical studies of the wetting properties of silicon surfaces patterned with pillars of two different diameters and heights with varying pitch values are presented. We propose a criterion where the transition from Cassie and Baxter regime to Wenzel regime occurs when the droop of the droplet sinking between two asperities is larger than the depth of the cavity. The trends are explained based on the experimental data and the proposed transition criteria. An environmental scanning electron microscopy (ESEM) is used to form smaller droplets of about 20 microm radius and measure the contact angle on the patterned surfaces. The investigation has shown that ESEM provides a new approach to wetting studies on the microscale.