Characterization of surface wettability plays an integral role in physical, chemical, and biological processes. However, the conventional fitting algorithms are not suitable for accurate estimation of wetting properties, especially on hydrophilic surfaces, due to optical distortions triggered by changes in the focal length of the moving drops. Therefore, here we present an original setup coupled with Convolutional Neural Networks (CNN) for estimation of Contact Angle (CA). The developed algorithm is trained on 3375 ground truth images (at different front-lit illuminations), less sensitive to the edges of the drops, and retains its stability for images that are synthetically blurred with higher Gaussian Blurring (GB) values (GB: 0–22) if compared to existing goniometers (GB: 0–12). Besides, the proposed technique can precisely analyze drops of various colors and chemistries on different surfaces. Finally, our automated orthogonal camera goniometer has a significantly lower average standard deviation (6.7° vs. 14.6°) and coefficient of variation (14.9 vs. 29.2%) than the existing techniques and enables wettability assessment of non-spherical drops on heterogeneous surfaces.