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Objective Fractals represent a type of derived geometric pattern that permits the characterization of the branching pattern of retinal vessels. We examined a new semiautomated method to measure retinal vessel fractals. Design Methodology study. Participants Three hundred randomly selected participants from the population-based Blue Mountains Eye Study. Methods We developed a semiautomated computer program to measure the fractal dimension ( D f ) of the retinal vessels from digitized images of disk-centered retinal photographs. Two trained graders masked to participant characteristics measured D f of right eye images of participants. Reliability was determined by repeat grading of the images from 60 participants, and association with systolic and diastolic blood pressure was examined in all 300 participants. Main Outcome Measure D f of the retinal vessels. Results Mean D f was 1.437 with a standard deviation of 0.025. Intragrader and intergrader reliability estimates were high with intraclass correlation ranging from 0.93 to 0.95. D f was inversely correlated with age ( r = −0.42, P = 0.001) and systolic blood pressure ( r = −0.29, P <0.0001). After adjustment for age and sex, mean D f was significantly lower in participants with than without hypertension ( D f difference 0.01, P = 0.02). Conclusions The D f of the retinal vessels can be reliably measured from photographs and shows a strong inverse correlation with blood pressure. These data suggest that the D f may be a measure of early microvascular alterations from elevated blood pressure. Further studies to examine the systemic and ocular correlates of the D f of the retinal vessels are needed. Financial Disclosure(s) The authors have no proprietary or commercial interest in any materials discussed in this article.