The specific rotation for two isomeric members of the terpene family, (S)-(+)-2-carene and (S)-(+)-3-carene, has been investigated under complementary solvated and isolated conditions, where the latter vapor-phase work has been performed at excitation wavelengths of 355 and 633 nm by means of ultrasensitive cavity ring-down polarimetry (CRDP). Linear-response computations of dispersive optical activity built upon analogous density-functional (B3LYP/aug-cc-pVTZ) and coupled-cluster (CCSD/aug-cc-pVDZ) levels of theory have been enlisted to unravel the structural and electronic origins of observed behavior. The six-membered portion of the bicyclic skeleton in the nominally rigid 3-carene system is predicted to be near-planar in nature, with calculated and measured rotatory powers for the isolated (gas-phase) species shown to be in excellent agreement. In contrast, the inherent flexibility of 2-carene gives rise to two quasidegenerate conformations that are interconnected by a large-amplitude ring-puckering motion and exhibit antagonistic chiroptical properties. Various approaches to simulate the intrinsic response evoked from a thermally equilibrated ensemble of gaseous (S)-(+)-2-carene molecules have been considered, including implicit averaging over independent conformers and explicit (albeit restricted) averaging over nuclear degrees of freedom. A polarizable continuum model for implicit solvation was found to describe solvent-dependent trends reasonably well in the case of (S)-(+)-2-carene, but failed to reproduce the specific-rotation patterns emerging from polarimetric studies of (S)-(+)-3-carene.