Herpes zoster infection, commonly known as Shingles, is caused by reactivation of the Varicella-Zoster virus which may have remained latent in the dorsal root ganglia. HZI is characterized by prodromal symptoms of unilateral deep aching, burning pain followed by a maculopapular rash, vesicular eruptions, ulcers, and scab formations over the affected nerve distribution. The ophthalmic branch of the trigeminal nerve is more commonly involved in HZI than maxillary and mandibular branches; in particular, the maxillary involvement is rare. This is a case report of HZI in a 65-years-old male patient involving the maxillary division of the trigeminal nerve. This case highlights the importance of early diagnosis and prompt use of antivirals in managing orofacial HZI in dental practice.