Cutaneous mastocytosis (CM) has been associated with urticaria, itching, and pain of the affected regions. Although the occurrence of CM in the facial skin is rare, it may be a cause of chronic facial pain, and pain characteristics may mistakenly be interpreted as trigeminal nerve pathology. However, the dermatological appearance of the different variants of cutaneous mastocytosis is distinct and should be considered as an uncommon differential diagnosis in an orofacial pain diagnostic algorithm. This article presents a case of telangiectasia macularis eruptiva perstans, a rare type of cutaneous mastocytosis, as the underlying cause of chronic facial pain, erythema, and swelling.