The self-assembly, organogelation, syneresis, and anti-adhesion properties of a peptidomimetic containing L-phenylalanine and 2,6-dimethylpyridine 3,5-dicarboxylic acid have been studied in detail. The peptidomimetic forms a transparent gel in aromatic solvents such as benzene, toluene, xylene and chlorobenzene. The hierarchical nature of the self-assembly process in the gel was characterized by a combination of POM and FE-SEM imaging, revealing an entangled fiber network. The rheology measurements then confirmed the formation of a thixotropic organogel. The storage modulus was about one order of magnitude higher than the loss modulus, which indicates the physical crosslinking in the organogel. The gel exhibits significant self-healing properties and allows diffusion of rhodamine 6G through the gel matrix. The peptidomimetic gel shows syneresis under an appropriate environment. The peptidomimetic organogel surfaces exhibit syneresis-induced anti-adhesion properties against ice and water. This peptidomimetic gelator molecule, being economically viable and easy to synthesize, has great prospects in materials chemistry.