Abstract Guest‐release induced responsive behaviors in nonporous organic solvate crystals remain elusive due to the lack of well‐defined diffusion pathways and the rarity of crystal‐to‐crystal transitions. Here, we report a pentiptycene‐derived nonporous organic solvate ( 1B ) that exhibits a striking blue → green → yellow thermochromic fluorescence sequence through a two‐stage crystal‐to‐crystal transformation. In the first stage, subtle gear‐like rotations transiently open a zigzag diffusion pathway, releasing dichloromethane (DCM) and generating a green‐emissive phase ( 1G ). In silicone oil, asymmetric bubble evolution during DCM release drives directional crystal propulsion. A second heating step triggers a ∼90° correlated gear rotation that reconfigures alkyl conformation and anthracene packing, producing excimer‐based yellow emission ( 1Y ). These coupled sequential optical, mechanical, and structural responses reveal a unique paradigm of guest‐driven dynamics in nonporous solvate crystals.