Merkel cell carcinoma (MCC) is a rare cutaneous neuroendocrine malignancy with a well-documented propensity for regional and distant metastasis. The rate of MCC metastasis to regional lymph nodes is reported at 23-45%, hence the consensus guidelines put forward by The American Joint Committee on Cancer (AJCC) and National Comprehensive Cancer Network (NCCN), recommending sentinel lymph node biopsy for clinically node-negative patients with MCC. Information regarding regional in-transit metastasis of MCC whilst scarce suggests that this is uncommon. We present a case of a 69-year-old male with a MCC of his forehead and no palpable lymphadenopathy. He underwent wide local excision with clear margins and a negative sentinel lymph node biopsy (pathological stage I), followed by adjuvant radiotherapy. He re-presented 10 months following his initial definitive excision and treatment with a massive dermal metastatic deposit in the ipsilateral temporal region. We also review the available literature on patterns and risk factors for MCC metastasis in general, with a particular focus on in-transit metastasis.