Direct write printing is restricted by the lack of dielectric materials that can be printed with high resolution and offer dissipation factors at radio frequency (RF) within the range of commercial RF laminates. Herein, we outline the development of dielectric materials with dielectric loss below 0.006 in X and Ku frequency bands (8.2−18 GHz), the range required for radio frequency and microwave applications. The described materials were designed for printability and processability, specifically a prolonged viscosity below 1000 cps and a robust cure procedure, which requires minimal heat treatment. In the first stage of this work, nonpolar ring-opening metathesis polymerization (ROMP) is demonstrated at room temperature in an open-air environment with a low-viscosity monomer, 5-vinyl-2-norbornene, using the second-generation Grubbs catalyst (G-II). Differential scanning calorimetry (DSC) was used to study how the catalyst activity is increased with heating at various stages in the reaction, which is then used as a strategy to cure the material after printing. The resulting cured poly(5-vinyl-2-norbornene) material is then characterized for dielectric and mechanical performance before and after a secondary heat treatment, which mimics processing procedures to incorporate subsequent printed conductor layers for multilayer applications. After the secondary heat treatment, the material exhibits a 55.0% reduction in the coefficient of thermal expansion (CTE), an increase in glass-transition temperature (T g ) from 32.4 to 46.1 °C, and an increased 25 °C storage modulus from 428 to 1031 MPa while demonstrating a minimal change in dielectric loss. Lastly, samples of the developed dielectric material are printed with silver overtop to demonstrate how the material can be effectively incorporated into fully printed, multilayer RF applications.