Cutaneous mastocytosis (CM) is a rare condition characterized by abnormal mast cell proliferation in the skin. We present the case of a 65-year-old man with recurrent urticaria-like rashes persisting for more than eight years. Despite multiple misdiagnoses as insect bites, examination and biopsy revealed mast cell infiltration. The patient's unique lifestyle, particularly his frequent seafood consumption, adds an intriguing dimension to the case. Treatment with systemic antihistamines and corticosteroids provided symptomatic relief, but long-term follow-up showed the persistence of clinical lesions, indicating that the treatment did not adequately address the underlying cause of the disease. A notable improvement in disease control was observed when the patient's diet was adjusted, suggesting a potential link between food and cutaneous mastocytosis. To our knowledge, this is the first documented case of maculopapular cutaneous mastocytosis in Syria.