Dermoid cysts are common periorbital lesions. They usually present early in life as mobile, palpable, well-circumscribed masses near the lateral brow. Transcranial extension of a superficial, nonmidline, periorbital dermoid cyst is rare. We report 2 cases of dermoid cysts of the lateral brow that were originally recognized during the newborn period. Over time, they appeared to be clinically resolved, but they presented years later with full-thickness bone erosion and transcranial extension. Excision was performed via a combined extracranial and intracranial approach. The treatment, pathophysiology, and natural history of orbitofacial dermoid cysts are reviewed.