Ice accretion is an unavoidable phenomenon that endangers the performance of outdoor infrastructure and vehicles at low temperatures. To combat ice accretion, the use of anti‐icing coatings has been one of the most appealing approaches because of their simplicity. Silicone elastomers have been increasingly employed due to their natural hydrophobicity, simple preparation, and low price. However, most of the characterization of silicone‐based polymers and other anti‐icing coatings has been done using unproven techniques that often do not directly relate to materials’ properties. In this work, the adhesion between glass and ice and four PDMS‐based elastomers has been studied by a combination of a macroscale shear test, a microscale technique (the Johnson–Kendall–Roberts (JKR) approach), and a commonly used push‐off test. Results are obtained at different temperatures and, importantly, different test velocities. The shear tests yield an energy release rate (the material's property related to adhesion) in the range of 1–10 J m−2, whereas the quasistatic JKR test yields values in the 0.1–0.5 J m−2 range for glass/PDMS interfaces. Ice/PDMS interfaces are found to have larger energy release rates in shear tests and lower values in quasistatic JKR tests. Both differences can be attributed to differences in interfacial crack dynamics.