Aortic calcification in the tunica media is correlated with aortic stiffness, elastin degradation, and wall shear stress. The study aim was to determine if aortic calcifications influence disease progression in patients with acute type A aortic dissection (ATAAD). We retrospectively reviewed a total of 103 consecutive patients who had undergone surgery for ATAAD at our institution between January 2009 and December 2019. Of these, 85 patients who had preoperatively undergone plain computed tomography angiography (CTA) for evaluation of their aortic calcification were included. Moreover, we assessed the progression of aortic dissection after surgery via postoperative CTA. Using a classification and regression tree to identify aortic Agatston score thresholds predictive of disease progression, the patients were classified into high-score (Agatston score ≥ 3344; n = 36) and low-score (<3344; n = 49) groups. Correlations between aortic Agatston scores and CTA variables were assessed. Higher aortic Agatston scores were significantly correlated with the smaller distal extent of aortic dissection (p < 0.001), larger true lumen areas of the ascending (p = 0.009) and descending aorta (p = 0.002), and smaller false lumen areas of the descending aorta (p = 0.028). Patients in the high-score group were more likely to have DeBakey type II dissection (p = 0.001) and false lumen thrombosis (p = 0.027) than those in the low-score group, thereby confirming the correlations. Aortic dissection in the high-score group was significantly less distally extended (p < 0.001). A higher aortic Agatston score correlates with the larger true lumen area of the ascending and descending aorta and the less distal progression of aortic dissection in patients with ATAAD. Interestingly, the findings before and after surgery were consistent. Hence, aortic Agatston scores are associated with aortic dissection progression and may help predict postoperative residual dissected aorta remodeling.