A large number of silicon (Si) patterns consisting of nanopillars of varying diameter and pitch have been fabricated and further coated with diamond-like carbon (DLC) and perfluoropolyether (Z-DOL) films. The wetting behavior and nano-adhesion/friction of the patterns are investigated experimentally in relation to the nanostructures and the hydrophobicity of the materials. Measurements of water contact angle illustrate that the patterning-enhanced wettability of the Si flat surface, along with two distinct wettings which are in good agreement with the Wenzel and hemi-wicking states, depended on the value of the pitch-over-diameter ratio. In the case of the coated patterns, three wetting states are observed: the Cassie-Baxter, the Wenzel, and a transition from the Cassie-Baxter into the Wenzel, which varies with regard to the hydrophobic properties of the DLC and Z-DOL. In terms of tribological properties, it is demonstrated that a combination of the nanopatterns and the films is effective in reducing adhesive and frictional forces. In addition, the pitch and diameter of the patterns are found to significantly influence their adhesion/friction behaviors.