The menisci are crescent-shaped fibrocartilaginous tissues featuring highly aligned collagen arranged in a circumferential fashion to allow transmission of loads across the knee joint. To mimic this macroscopic orientation, we developed a novel electrospinning method to collect circumferentially aligned (CircAl) fibers, quantified their structure and mechanics, and compared them to linearly aligned (LinAl) scaffolds. Fiber orientation of CircAl scaffolds varied considerably as a function of position (p 0.05). Alterations in cellular alignment on a macroscopic scale were observed on the CircAl scaffolds. Mechanical analysis of the CircAl scaffolds revealed significant interactions between scaffold length and region (p 0.05). In conclusion, we developed electrospun nanofibrous scaffolds with a spatially varying macroscopic fiber orientation, creating a gradient in fiber alignment and differences in tensile properties over a macroscopic scale. These organized nanofibrous scaffolds can potentially direct the formation of an anatomic meniscus construct with structure and function that vary across a large anatomic expanse.