Herein we describe intramolecular cascade reactions enabling the synthesis of bridged cyclopropanes, via the photoinduced energy-transfer catalysis of tethered conjugated dienes. Photocatalysis affords the efficient synthesis of complex tricyclic compounds that exhibit multiple stereocenters from readily accessible starting materials that would otherwise be difficult to obtain. This single-step reaction is characterized by its broad substrate scope, atom-economy, excellent selectivity, and satisfactory yield, which includes a facile scale-up synthesis and synthetic transformation. An in-depth mechanistic study reveals that the reaction proceeds via an energy-transfer pathway.