High speed machining (HSM) can reduce machining time with the high metal removal rate by high speed spindle and feedrate. This paper supports HSM technology using the small size tool with the optimal tool path generation and modification of tool change. The optimum tool path is generated to reduce cutting length of cavity pattern and change the cutting tool for preventing the tool breakage by wear. The tool path is modified with the experiment data of tool wear and breakage to support tool change on reasonable time. The result can contribute to HSM technology of high hardness materials using the small size end-mill.