Strain energy is a fundamental measure of the steric and configurational properties of organic molecules. The ability to estimate strain energy through quantum chemical simulations requires at minimum the knowledge of an initial set of nuclear coordinates. In general, such knowledge is not categorically known when screening or generating large numbers of molecule candidates in the context of molecular design. We present a machine learning approach to predict hydrocarbon strain energies using Benson group equivalents. A featurization strategy is crafted by concatenating the molecule group equivalent counts with easily computable molecular fingerprints. The data are obtained from electronic structure calculations we performed on a set of 166 previously synthesized strained hydrocarbons. These data are provided and include gas phase enthalpies of formation and associated optimized atomic coordinates. The strain energy prediction accuracy of several statistical learning methods is evaluated, and their respective merits and limitations are discussed.