Alkene-bridged calix[4]arene monomers were synthesized by ring-closing metathesis (RCM). All the three possible conformers (cone, partial cone, and 1,3-alternate) were used as comonomers with cyclooctene and norbornene in ring-opening metathesis polymerization (ROMP). The resultant polymers were high-molecular-weight, transparent and stretchable materials with high calixarene incorporation (up to 25 mol % or 70 wt %) and low glass transition temperatures.