We present the first case of a woman with no significant medical history who developed dissections of bilateral carotid and bilateral vertebral arteries, as well as a retinal artery occlusion, after a roller coaster ride. A 35-year-old woman developed right-sided neck pain followed by a frontal headache immediately after a roller coaster ride. Five days after the incident, she developed complete loss of vision in her right eye for two hours. Subsequently, the vision improved but remained significantly decreased. On presentation, her visual acuity was 20/200 in the right and 20/20 in the left eye. Her fundus exam revealed retinal edema in the superotemporal retinal artery distribution without any visible emboli. Her neurological exam was otherwise normal. The cerebral angiogram showed bilateral internal carotid and vertebral artery dissections. The patient remained stable with conservative therapy without further worsening of vision or any new neurological deficits. Outcomes for cervicocephalic arterial dissection are usually favorable, but early diagnosis is critical for initiation of appropriate treatment of possible complications. Physicians must have a high index of suspicion for arterial dissection when patients note any headache, neck pain or vertigo triggered by violent motion after leisure activities such as roller coaster rides.