The purpose of this study was first to determine the normal blood supply of the heel entheses with cadaver injection, and second, to identify by means of ultrasound (US) this blood supply in healthy volunteers before and after the intravenous injection of a US contrast agent (SonoVue). Twenty cadaver lower limbs were cut into sagittal, coronal, or axial sections after the injection of a red-colored gelatin solution. Ten anatomical samples were selected for histology. Then 10 healthy volunteers were enrolled in a contrast-enhanced ultrasonography study (CUS). Calcaneal tendon and plantar aponeurosis entheses were studied first without any contrast-agent (B-mode, power Doppler). A single dose (2.4 ml) of the contrast agent was then administered for studying each enthesis of the right foot. The operators had to look for blood flow within the entheses and in the adjacent soft tissues. Anastomotic transverse branches were seen macroscopically at the back of the calcaneal tendon, giving some capillaries penetrating the enthesis. None of these vessels could be seen with CUS. In contrast, a high-density vascular network could be detected in Kager’s triangle with CUS. No blood vessel could be seen within the plantar aponeurosis enthesis, either macroscopically or microscopically. No evidence of entheseal vascularization was found with any contrast-enhanced imaging technique. Inferior branches of the lateral plantar artery were seen on coronal and sagittal sections of the hindfoot, and could be detected with CUS. These arterioles were running toward the anterior aspect of the calcaneal tuberosity, near the plantar aponeurosis insertion. In conclusion, no vascularization was detected with CUS at the cortical bone insertion of normal heel entheses. However, some vascularization could be seen in the immediate vicinity of heel entheses. The latter feature has to be kept in mind, as it may represent a pitfall for the diagnosis of early inflammatory changes in patients, especially those with seronegative spondylarthropathies.