To the best of our knowledge, no study using neuroimaging modalities has documented calvarial diploic veins (DVs) connected to the extracranial sites. This study aimed to characterize them using magnetic resonance imaging (MRI). A total of 88 patients underwent thin-sliced contrast MRI. In addition, the DVs coursing through the pterional area were observed on three injected cadaver heads. On postcontrast MRI, the DVs of the pterional area directly drained into the temporalis muscle or supplied branches coursing into the muscle in 43% on the right side and 40% on the left. The DVs and their branches were highly variable in diameter and number. In 9% of cases, the DV of the pterional area was found to drain into an extracranial site and connected to large venous channels distributed in the temporalis muscle. Furthermore, in 17% of cases, the DVs drained into the extracranial sites in the frontal skull region, followed by 9% in the parietal, 2% in the occipital, and 1% in the temporal regions. The DVs coursed superficially in the pterional area on both sides of all three cadaver heads. On one side, the DV in the area was open to an extracranial site. Part of the diploic venous flow drains extracranially in the pterional area. This area may provide an important interface between the calvarial DVs and the extracranial venous system.