Two recent cases of glomus tumors (GTs) of the gastrointestinal tract presented with symptoms of GI bleeding. GTs, typically benign lesions of mesenchymal origin, are rarely seen in the GI tract, and most commonly involve the distal appendages. This case series discusses the tumor biology, presentation, imaging, endoscopic findings, pathology and management of GTs. While diagnosis of GTs is typically made on final surgical pathology, there are defining characteristics that can separate a GT from a gastrointestinal stromal tumor on endoscopic ultrasound (EUS) and CT imaging. The classic pathological findings are discussed, and surgical decision-making is reviewed. New developments in the form of EUS-guided biopsy and endoscopic submucosal dissection present new avenues for diagnosis and treatment of submucosal lesions of the GI tract, including GTs. While typically a benign tumor requiring no adjuvant therapy, this study discusses some very rare cases of metastatic GT in the literature.