We report a 47-year-old male with extreme dilatation of the Stenon's duct resulting from parotid papilla obstruction. He visited our clinic with a painless swelling in his left cheek and oral cavity after eating. The swelling had been present for four months. Physical examination, computed tomography, and magnetic resonance imaging showed that the lesion was due to extreme dilatation of the Stenon's duct. The obstruction was corrected by the surgical creation of a new, larger orifice. The cheek swelling immediately disappeared and has not returned after three months. Endoscopic examination of the Stenon's duct using a dacryoendoscope and nasal endoscope was carried out during surgery. These endoscopes were easily inserted into the Stenon's duct and provided adequate resolution of images of the duct lumen. Inflammatory debris and ductal swelling with hyperemia were observed in the lumen and gradually diminished from the parotid papilla to the parotid gland. In the parotid gland, the lumen was dilated, but did not show debris or ductal swelling. This endoscopic examination was very useful in understanding the etiology of the extreme dilatation of the Stenon's duct.