It is anticipated that concentrated solar power (CSP) plant will become one of the significant resources for electric power generation in the near future. As the smaller scale CSP-based generations are primarily connected in distribution systems, there is a need to assess risk-based security for mid- to long-term planning. To quantify the risk of static and dynamic security with CSP, a method based on chronological simulation has been proposed. A clustering, algorithm-based scenario-reduction technique has been used to utilise the data efficiently for chronological simulation while preserving the temporal information. A number of composite risk indices that truly reflect the system risk have been used to address the static and dynamic security of a distribution system. The proposed method has been applied to a medium voltage distribution system, 43-bus system, to evaluate the static and dynamic risk with CSP and electric vehicles using the load profiles of North Queensland. Power profiles of a CSP system at Rockhampton, North Queensland, have been used for the simulation studies.