Prostate cancer is the second most common cancer in men worldwide. While clinicians commonly see metastases to the bones and lymph nodes, it may infrequently spread to more uncommon locations. We report an unusual case of an 83-year-old patient with previously treated prostate adenocarcinoma who presents with symptomatic metastases to the testis and brain in the absence of widely disseminated disease. This case report highlights the importance of including metastatic disease in the differential for patients with a history of prostate cancer and a newly discovered mass until an evaluation of the tissue can be performed.