Headache is a frequent emergency department (ED) complaint. Secondary headache, due to infectious causes, must be carefully evaluated as a differential diagnosis. Red flag signs and classic physical examination findings are available to aid the diagnosis and evaluation of secondary headache. These findings, however, are limited by poor sensitivity and predictive value. We present a case of Herpes zoster (HZ) meningitis in a young healthy male adult with major presenting symptom of headache and new-onset rash to underscore the variation in atypical presentations of aseptic meningitis. HZ-associated aseptic meningitis often presents with characteristic, but at times atypical rash. We recommend skin lesions be thoroughly evaluated, along with classic signs of fever and nuchal rigidity, to assist in the diagnosis of meningitis.