Ultra High Molecular Weight Polyethylene (UHMWPE) has been used as a ski sole material for many years due to its good tribological properties, good wear resistance and low friction coefficient. Recent studies have showed improved performance on wear rate and hydrophobicity with nanoparticle reinforced UHMWPE. In this study, different kinds of nano-composite UHMWPE’s were tested on snow to investigate if they are suitable as a ski sole material and to find the type of nano-composite UHMWPE that has the greatest potential. Further, the mechanisms of hydrophobicity and its influence on the friction level were examined. The friction coefficient was measured in a ski test rig and simple demonstrations under a microscope were made to simulate how water is dragged along the ski sole in contact with wet snow. Mechanical properties were measured with a CSM Nanoindentation Instrument and surface topography was examined in a Wyko Optical Profiler. The cross-linked UHMWPE material showed the lowest friction coefficient on snow. The hydrophobic demonstrations, together with the ski test results, questions the suggestion that high hydrophobicity enhances the ski glide. Nanoindentation was proved to give valuable data for mechanical properties, but it should be questioned whether it is a good technique for comparing different nano-composite UHMWPE materials. The ski tests show the importance of the characteristics of snow.