Physical importance of cutting temperatures has long been recognized. Cutting temperatures have strongly influenced both the tool life and the metallurgical state of machined surfaces. Temperatures in drilling processes are particularly important, because chips remain in contact with the tool for a relatively long time in a hole. Tool temperatures tend to be higher in drilling processes than in other in machining processes. This paper concerns with modeling of thermal behaviors in drilling processes as well as estimation of the cutting temperature distribution based on remote temperature measurements. One- and two-dimensional estimation problems are proposed to analyze drilling temperatures. The proposed thermal models are compared with solutions of finite element methods. Observer algorithms are developed to solve inverse heat conduction problems. In order to apply the estimation of cutting temperatures, approximation methods are proposed by using the solution of the finite element method. In two-dimensional analysis, a moving heat source according to feedrate of the drilling process is regarded as a fixed heat source with respect to the drilling location. Simulation results confirm the application of the proposed methods.