The first public school in Annawan was organized in 1854 and was held in the Village townhouse. The townhouse was a meeting hall which was also used for trials and village board meetings.

In 1870 a two-story frame building was constructed on a one square block site close to the business district. This block served as an educational site for the next 104 years.

As the demand for additional education grew, two years of high school were added to the curriculum. An additional year of high school courses was added in 1911 to make a three-year course of study.

On May 10, 1912, the people living in sections 19 through 36 in Alba Township and in sections 1 through 24 of Annawan Township voted 92 to 77 to organize Annawan-Alba High School. The course of study gradually grew into a four-year curriculum.

On June 19, 1920, the residents of the Annawan and Alba Townships comprising District Number 124 and the outlying districts composed of Annawan Number 125, Palmer Number 126, Ferguson Number 129, Dwyer Number 130, Harrison Number 131 and Pritchard Number 133 voted 172 to 102 to form the Annawan Community Consolidated School District. The residents of Kedron District 129 voted 33 to1 in 1921 to be annexed.

A fire starting on the roof when sparks fell on the belfry on February 2, 1922, destroyed the two-story wood-frame school building and all of its contents. During the emergency period following the fire, classes were held in the Baptist Church, the Village Hall, Sacred Heart School, and the backroom and second floor of Legers Department Store.

The general disorganization resulting from the loss of the school building resulted in a vote of 324 to 146 on September 29, 1923, to discontinue Community Consolidated School District and to reorganize into the former common school districts.

The Board of Directors of Annawan School District 125 and the Board of Education of Annawan-Alba High School District 188 planned and built a two-story brick structure to house a combination grade and high school. The building was completed on March 2, 1925, and dedicated on March 24. Increased enrollments and an expanding curriculum made it necessary to increase the building space. In 1937 and 1938 an extensive two-story addition measuring 93 feet by 43 feet and built at a cost of $25,000 was added. The new addition housed an agriculture classroom and shop, a science room and a home economics room. Later the study hall was enlarged and a library was added.

Sections 1 through 18 of Alba Township and Sections 13, 25, 26 and 36 of Cornwall Township were annexed to the district by petition on September 8, 1941. This increased the area of the district to 66 square miles. In 1947 Sections 13 through 36 of Yorktown Township were annexed to the district increasing the size to 90 square miles.

The current Annawan Community Unit District 226 was formed in 1948. The district contained nearly all of the territory of the former Annawan-Alba Township High School District with additions which included territory from Burns and Lorraine Township. The new unit district also contained the former Hooppole Grade and High School Districts and the country schools comprised of the Pritchard School, Harrison School, Kedron School, Ferguson School, Union School, Baker School, Moon School, Acme School, Burns School, McLaughlin School, Holdridge School, Holzinger School, Maple Grove School and Blim School.

The unit district brought about many improvements in facilities and services. The outdoor athletic complex was laid out in 1947 and a combination bus garage and industrial arts shop was built on the east side of the field. Student transportation was inaugurated in the district with the purchase of four buses. The district increased its fleet by two buses during the 1948 and 1949 school years. The school lunch program was inaugurated at the beginning of the 1950-51 school year with the addition of kitchens and dining facilities at the Annawan and Hooppole schools. The Annawan School was expanded during the same year when the Union School building was moved to Annawan and annexed to the east side of the Annawan School. This provided one more room for grade school students.

In 1964 a new elementary school was built in Hooppole. The building contained five classrooms, an all-purpose room, a cafeteria, health room, and administrative offices. In 1972 district voters approved a new elementary building which included a unit media center, additional high school classrooms and a centralized music and art complex for K-12 students. The air-conditioned building was located adjacent to the high school. The erection of this structure was necessitated due to the outdated and deteriorating condition of the Annawan and Mineral Grade School buildings. The building was officially dedicated on January 19, 1975.

In 1973 the District had a total enrollment of 728 pupils composed of 480-grade school students and 248 high school students. This was the highest district enrollment. The high school enrollment peaked with 252 students during the 1975-76 school year.

During the late 1970s and early 1980s steps were taken to improve the financial status of the district. A major step, due to declining enrollment, included the closing of the Hooppole Grade School at the conclusion of the 1979-80 school year. In the fall of 1980, the district departed from using a bus contractor and assumed ownership of the buses. A loan of $150,000 was secured from the State Bank of Annawan to purchase a fleet of ten buses. An additional bus storage and maintenance facility were built with the funds realized from the sale of the Hooppole School.

During the 1980s and ’90s, there were many academic changes instituted. The district was one of the first in the state to adopt an all-day kindergarten program. In 1990 a Pre-School program was initiated for three and four-year-old students. A calculus class offered through Black Hawk College and taught at Annawan High School was started. In 1997 Spanish was added to the elementary curriculum. The district continued to pride itself on its academic recognition and achievements. Annawan High School consistently ranks at or near the top of the schools in the Henry-Bureau-Stark County area on ACT college entrance scores. The School was ranked in the top ten on ACT scores in the State of Illinois on three occasions during the late ’80s and ’90s. The school's IGAP scores for all grade levels have been excellent since the test was initiated by the state.

The district purchased its first computer and printer in 1981 for a price of $2824. In 1998 the district became a leader in the area of technology with a well-trained staff, three computer labs, five mini labs and internet access in nearly all the classrooms. The ratio of students to computers is 4.22 to 1. The staff has been successful in incorporating technology into many curriculum areas.

As we prepare to move into the 21st century the financial climate of the district is excellent, the facility is in very good shape and the staff is highly qualified to meet the challenges which lie ahead.

The Community Unit School District had a total of 388 pupils in 1993 at its four attendance centers: Hooppole Grade, Annawan Grade, Pritchard grade, and Annawan High School. The District was continuing to grow and in 1956 a new school was erected on a 10-acre site in the southwest corner of the village. The building contained classrooms, a cafeteria, gymnasium, health facilities, and administrative offices.

The district expanded again in 1961 with the annexation of the majority of the Mineral School District. After their inclusion in the Community 226 District, attendance centers were located in Hooppole, Mineral, and Annawan. The district was composed of 120 square miles.