Trochleitis is a very rare form of inflammation that occurs in the trochlear region. It is characterized by periorbital pain, diplopia, blurred vision, frontal headache, trochlear tenderness, and radiologic signs of inflammation. We report a case of an 18-year-old man who experienced unilateral eye pain, double vision, and tenderness when looking upward. Initially, his pain was misdiagnosed as migraine for more than two months. The patient did not show improvement with NSAID treatment, leading to successful treatment with a steroidal injection. Although rare, healthcare providers should maintain a high index of suspicion to avoid misdiagnosis of this type of eye pain.