In this study a two-stage stochastic programming joint day-ahead energy and reserve scheduling model to address uncertainty in wind power generation is developed. Apart from the generation side, the demand side is also eligible as a reserve resource and is modeled through responsive load aggregations, as well as large industrial loads that directly participate in the scheduling procedure. The main contribution of this paper is the inclusion of a risk metric, namely the Conditional Value-at-Risk (CVaR), which renders a conceptually different resource scheduling framework. The proposed model is employed in order to analyze the behavior of energy and reserve scheduling by both generation and demand for a risk-averse Independent System Operator (ISO). To reach practical conclusions, the proposed methodology is tested on the real non-interconnected insular power system of Crete, Greece, which is characterized by a significant penetration of wind power generation.