Impacts with trees and wooden utility poles represent a significant subset of vehicular collisions. For example, while fixed object collisions account for less than 8% of all crashes, they represent nearly 30% of all fatal crashes. Also, nearly half (over 43%) of all fixed-object impacts are into a tree, pole, or post. This paper is viewed as a first attempt to understand the energy absorbing processes operating when vehicles strike trees and wooden poles in order to make reasonable estimates of the magnitude of the tree/pole energy dissipated in the crash. This initial study is comprised of a literature review, a series of scale model pole/pendulum impacts, and an analytical study which is comprised of both a static analysis and a dynamic finite element model (FEM) analysis of a vehicle/pole impact. As a result of this work, a methodology has been evolved for making estimates of tree/pole energy. This methodology considers whether or not the struck object was displaced in its moorings and/or partially or completely fractured by the impact.