This article considers the thermodynamic aspects, thermo- and rheokinetics of endo-dicyclopentadiene polymerization in the presence of the original metathesis second Hoveyda-Grubbs catalyst with an N-chelating ligand. The activation energy of endo-dicyclopentadiene polymerization was determined as 88.9–89.2 kJ/mol. The thermal effect of the ring-opening metathesis endo-dicyclopentadiene polymerization reaction reaches 52.7 kJ/mol. This is lower than the values for molybdenum- and tungsten-containing catalysts reported in the literature, which can be explained by a different microstructure of the polymer produced in the presence of ruthenium-based metathesis catalysts.