The ground state potential energy surface of the model molecular rotor 2-cyclopentylidene-tetrahydrofuran (CPTHF) has been characterized by calculating minimum energy conformations, racemization pathways, and rotational barriers with high level ab initio electronic structure calculations. Two conformers with their corresponding enantiomers are found. The activation barriers for racemization are negligible, therefore thermal racemization takes place at room temperature. Torsional transition states, calculated using multiconfigurational CASSCF calculations, show twisted and pyramidalized biradical structures. Additionally, the photochemistry of CPTHF has been investigated using the accurate MS-CASPT2/CASSCF methodology. In the UV spectrum it is found that the spectroscopic state is the SI, which corresponds to a pi pi* transition within the ethylene moiety. To understand light-triggered isomerization around the C=C bond, five conical intersections between the S-0 and S-1 have been located for each conformer of CPTHF, which allow the system to rapidly decay to the electronic ground state.