The Dubins path problem had enormous applications in path planning for autonomous vehicles. In this paper, we consider a generalization of the Dubins path planning problem, which is to find a shortest Dubins path that starts from a given initial position and heading, and ends on a given target circle with the heading in the tangential direction. This problem has direct applications in Dubins neighborhood traveling salesman problem, obstacle avoidance Dubins path planning problem etc. We characterize the length of the four CSC paths as a function of angular position on the target circle, and derive the conditions which to find the shortest Dubins path to the target circle. The Dubins path problem had enormous applications in path planning for autonomous vehicles. In this paper, we consider a generalization of the Dubins path planning problem, which is to find a shortest Dubins path that starts from a given initial position and heading, and ends on a given target circle with the heading in the tangential direction. This problem has direct applications in Dubins neighborhood traveling salesman problem, obstacle avoidance Dubins path planning problem etc. We characterize the length of the four CSC paths as a function of angular position on the target circle, and derive the conditions which to find the shortest Dubins path to the target circle.