Varicella zoster virus (VZV) is an exclusively human, double-stranded DNA virus. Primary infection causes varicella (chickenpox); later the virus becomes dormant in the dorsal root, cranial nerve, and autonomic ganglia along the entire span of the nervous system, retaining the capacity to reactivate and cause a variety of dermal and neurological complications. Recently there has been increasing recognition, both clinically and epidemiologically, of the relationship between VZV and subsequent strokes. Herein, we describe a case of a previously healthy individual with reactivation of VZV causing herpes zoster opthtalmicus along with devastating multifocal vasculopathy. It is crucial for dermatologists to recognize the dermatomal vesicular eruption in this high risk area to aid in prompt diagnosis in an effort to improve clinical prognosis.