A 73-year-old woman with a history of right hemicolectomy for advanced ascending colon cancer 14 years earlier was referred to our facility for a 2-month history of solid food dysphagia. An esophagogastroduodenoscopy revealed a 7-cm fungating and ulcerated mass in the middle to lower esophagus. The biopsy from the esophageal mass showed a moderately to poorly differentiated squamous cell carcinoma. A colonoscopy showed an end-to-end ileocolonic anastomosis with a 7-mm ulceration in the transverse colon. The biopsy of the ulceration at the anastomotic site showed a moderately to poorly differentiated squamous cell carcinoma with a morphology similar to that of the esophageal mass, rendering the diagnosis of metastatic esophageal squamous cell carcinoma. Colonic metastasis from esophageal squamous cell carcinoma, especially at the anastomotic site, is extremely rare. Although surgical trauma may not have contributed to the anastomotic site metastasis, given the distant timeline, its role in the pathogenesis of metastasis cannot be completely ruled out.