Objectives: This study aims to analyze the risk factors for local recurrence (LR) following pancreaticoduodenectomy (PD) in pancreatic cancer patients and to identify associated vascular features associated. Background: Pancreatic cancer frequently involves the mesenteric root, particularly the Porto-mesenteric vein (PV-SMV), impacting survival post curative surgery. However, the relationship between vascular structural changes and LR post-operation remains unclear. Methods: Retrospective data collection was conducted at a single tertiary center from December 2010 to March 2021. Clinical characteristics, surgical-pathological factors, and radiological features were compiled. Results: A total of 203 pancreatic cancer cases undergoing PD were analyzed, with 72 (35.5%) undergoing concurrent PV-SMV resection (VR). Median overall survival post-operation was 22.4 months. LR occurred in 121 patients (60%) at a median time of 8 months postoperatively. Resectable disease exhibited significantly longer local-recurrence free survival compared to borderline resectable/locally advanced pancreatic cancer (BRPC/LAPC) (median 14.5 versus 7 months, p<0.001). The most frequent sites of LR were the mesenteric root (37%), superior mesenteric artery (SMA, 21%), and superior mesenteric vein (SMV, 16%), with similar patterns observed in the VR and non-VR groups. BRPC, LAPC, postoperative CA19-9 above normal range, venous thrombosis, and stenosis were associated with LR (HR: 2.1, 2.7, 1.8, 2.0, and 1.6, respectively), while PV-SMV resection and enlargement of PV-SMV angle were protective factors (HR: 0.4 and 0.3). Conclusions: Despite aggressive treatment strategies including neoadjuvant therapy and radical surgery, LR in pancreatic cancer remains a challenge. This study highlights potential risk factors, recurrence patterns, and associated vascular features for early identification.