Numerous experimental methods are available to characterize surface hydrophobicity and water-surface interactions. The contact angle of a macroscopic droplet is a commonly used metric for hydrophobicity that can be measured by optical methods; larger contact angles are typically associated with stronger repulsion of water and thus higher hydrophobicity. While appealing for its simplicity, contact angle measurements may fail to adequately describe systems with nanoscopic heterogeneities and otherwise do not precisely has been used to quantitatively probe hydrophobicity for several systems, such as protein interfaces and self-assembled monolayers. Other simulation-accessible metrics for the hydrophobicity of surfaces might be derived from surface composition, density profiles, potentials of mean force, and structural order parameters involving water in proximity to interfaces. Nonetheless, these nanoscale structural and thermodynamic measures of hydrophobicity are rarely compared amongst each other and to possible macroscopic observations.