A bridge bearing anchor transmits various loads of a superstructure to a substructure. However, most anchors are generally designed without consideration of characteristics such as concrete pedestal, grout bedding, and anchor socket. Therefore, this study investigated the shear behavior of anchors in accordance with the edge distance, embedment depth, compressive strength of concrete, and height of the concrete pedestal in order to simulate the practical characteristics of the bridge bearing anchors. The actual shear capacity of the anchor differs from the shear strength calculated by the ACI 318 Code; especially, the importance of the embedment depth is underestimated in the code. An increase in the height of the concrete pedestal has a negative effect on the shear capacity because of the stress concentration. The grout is fractured prior to the occurrence of local damages in concrete, resulting in a secondary moment. As a result, the effect of the level arm is observed. An equation, which can predict the relative cracking degree of concrete, is proposed by analyzing the displacement of grout and concrete. High strain occurs in the stirrups close to the anchor, and the behavior of the strain is more influenced by the embedment depth than the edge distance. Finally, the design equation of concrete breakout strength is modified to predict the more precise shear resistance of a bridge bearing anchor.