First- and second-generation Newkome-type dendronized norbornene macromonomers were synthesized and polymerized by ring-opening metathesis polymerization (ROMP). In the case of the second-generation macromonomer, the rate of polymerization was highly dependent on the initial concentration of the macromonomer; quasi-quantitative polymerization was only achieved when the concentration was higher than 50 mM. Adding a linker between the polymerizable group and the dendron increased the rate of polymerization and it was possible to reach quantitative conversions at lower concentration. Doubling the length of the linker further improved the polymerization to a rate comparable with the polymerization of the first-generation dendronized macromonomer. The dendronized polymers presented herein consist of a poly(amide)-based dendron attached to the poly(norbornene) backbone. Because of the properties of these components such as biocompatibility, we foresee these polymers having possible applications in therapeutics.