Growing demand for forest machines that cost less to operate than current compared to traditional hydraulic and mechanical ones, along with regulatory pressures for lower emissions, is increasing manufacturers’ interest in developing electric and hybrid drives. While purely electric drives of forest machines meet a lot of bottlenecks (costs of the electric components, battery durability, duration of charging, access to the electrical grid, size of batteries that can ensure enough energy for 8 h working time), electric hybrid drives offer a favorable solution for the propulsion of forestry machinery in terms of lower fuel consumption and improved efficiency. Among all forest vehicles, specialized forest tractors (skidders), so far, have not been considered for forest vehicles with hybrid drive capabilities. A skidder is a forest-articulated self-propelled vehicle for pulling trees or parts of trees. In most countries in southern Europe, the use of skidders equipped with forest winches is the most common technique for timber extraction. The first goal of the research is to develop methods for measuring the energy consumption of skidders at different operating tasks and under different field conditions. Research was performed on the skidder Ecotrac 140V (from Croatian producer Hittner Ltd.) during timber extraction in mountainous terrains in Lika–Senj County. The skidder was equipped with a measuring device WIGO-E (Telematic Data collector) gateway with an integrated GPS system, which ensured data were collected from sensors and motor and stored in a computer via CANBUS and data transfer with GSM to Web platforms. Additionally, a fuel-flow meter was installed on the skidder. Data on fuel consumption (mL), position (traveling route), detection of winch work, engine rpm (min−1), engine torque (% of max), throttle position (%), and engine temperature were measured with a sampling frequency of 5 s. Furthermore, skidder load volumes per cycles and slopes of tractor paths were constantly measured. The paper shows the skidder’s energy consumption per day, work cycle, and individual work procedure with regard to the size of the load, the slope of the tractor path, and the direction of movement based on overlapping and merging all measurement data. Using mathematical and simulation models of the drive with defined operating cycles obtained by measurement, the possibilities of the hybrid drive and the dimensions of the elements of the hybrid drive (internal combustion engine, electric motor, batteries, control unit) were determined and are presented in this paper.