Public Schools - The Randolph Central School Corporation in Winchester is comprised of two grade schools, one middle school and one high school. Approximately 1,700 students are enrolled in the school system. The high school has a complete audio and light equipped auditorium, a gymnasium, a fieldhouse with seating for 2,500, a standard size football field with track, and six tennis courts. In addition, the RCSC has won numerous state recognition awards for its innovative approach to education. Their curriculum includes special programs for gifted and talented, special needs students, music, art, computers and technology. A strong vocational department is featured at the secondary school level as well as the opportunity for current students to take entry level university classes for college credit during their senior year. An extensive work-release program also can benefit students who have an interest in related fields. Adult education classes are offered at the high school in areas ranging from Basic Education to computerized drafting and vocational certifications.

Colleges and Universities - Although Winchester does not have a college or university, there are several within a 50 mile radius. Ball State University is located west of Winchester in Muncie, Indiana, and south of Winchester in Richmond is Earlham College and Indiana University East. In Ohio, there are three higher education facilities within 55 miles. The University of Dayton, Wright State University at Dayton and Edison State Community College at Piqua. All of these colleges and universities offer a wide variety of graduate and undergraduate courses.

Technical Training - Technical training can be obtained at Indiana Vocational and Technical schools at Richmond and Muncie, Indiana.