The objective of this study is to find the right path of evaluating middle school art and essay writing, therefore have developed this assessment data. A Written essay is expressing a personal opinion regarding a topic given, so this should be measured in a qualitative evaluation system and the process itself can be regarded as the center of the assessment. Rating student regarding essay writing requires education focused by school education. It is composed of teaching and studying researching discussion. It helps students upgrade their comprehensive thinking and understandings based on knowledge from school lecture and textbooks. This research gives student evaluation materials derived from revised arts course in 2009 and following 10 types of middle school arts textbook which includes essay writing. It also suggests direction to develop questions on essay writing and guides procedure about how to execute them. In addition, a new type of evaluation method known as “Achievement Assessment” was develop to measure student writing based on student achievements. Through the development of art and essay writing evaluation, a new way of learning and teaching skill was developed and applied onto 3rdyear of middle school students. A survey was conducted and analyzed based on teacher and student written testimony with the result of finalizing the written essay evaluation. Through this research new essay writing related teaching and learning was developed. In this based class students are able to carry discussion among peers and express their own taught. After this new method of teaching and learning class a questionnaires was conducted and analyzed which showed a high level of satisfaction and engagement from students. Also throughout the class students showed positive and continuous engagement during discussion as well has evaluation. Since during art and essay writing evaluation class the floor was open to students for discussion students were able to freely express their idea and opinion. Through this type of learning it is expected to improve student interest of evaluating arts. In order to settle art and essay writing in the educational field educator must be trained in various type of field, develop hands on learning experience, continuous updates on learning and more. Through this research it is expected to deliver proper ways of teaching method of art and essay writing.