Anomalous production of W + jet-jet events is possible at the Tevatron in many theories of new physics such as technicolor and extended gauge models. We outline methods for searching for new heavy particles, X, via the decay X -> W_jj with and without jet b-tagging. We estimate the sensitivity to W' -> WZ, Z' -> WW and p_T -> W_jj for Run II(2 fb^-1) and TeV33(30 fb^-1) and discuss some of the challenging experimental problems associated with searching for technicolor signatures.