In this work, a technique, based on using CAD/CAE software, is proposed for strength analysis of medium-voltage overhead lines (OHL). Firstly, the wind loads acting on OHL and on nearby woodland were estimated by the finite volume method. The wind loads were analyzed for different-shape cutouts of the surrounding forest as well as in the cases of coniferous, foliage and mixed forest. Then, the strength and frequency analysis of the woodland trees and the OHL poles and bare cables was done by the finite element method. Concrete numerical data obtained by the finite element solution are given for two types of conductors – aluminum wires and steel–aluminum wires of stranding. Also experimental data (pulling charts) obtained on the pulling testing machine Zwick Roell are given for the wires exploited in the regions of OHL damages. Additionally, buckling analysis from snow loads on the conifer and foliage trees was carried out. As can be seen, the comprehensive strength and buckling analysis of different elements of OHL can be carried out by using the proposed technique and software. Particular recommendations are given based on the obtained simulation results. A possible economic efficiency is discussed for the use of isolated cables and specially designed falling supports for the cables that do not allow interruption of the cable and breaking of the medium voltage OHL in case of extreme loads from falling trees.