Education has long been a priority within the Webster Groves School District. In fact, the organization of the Webster Groves School District predates the incorporation of the City of Webster Groves by 28 years.

On August 25, 1868, a group of 21 citizens voted unanimously to organize a district. A census was taken a month later, and 255 school-aged children were found. Three teachers were chosen and classes began on October 11, 1869 in rooms rented from the Congregational Church.

What has followed is more than 130 years of additional milestones and memories.

• 1866 The first public school in Webster opens, serving the African-American community
• 1868 Old Orchard School (later Lockwood School) opens
• 1869 Webster School (later Bristol School) opens
• 1889 A ninth-grade course - the first high school in Webster - is started by Miss Sarah Milligan
• 1890 Rock Hill School (later Schall School) opens
• 1892 Douglass School opens
• 1896 Selma School (later Mark Twain, then Margaret Goodall School) opens
• 1901 Old Orchard School District merges with Webster Groves School District
• 1907 Webster Groves High School opens; the Class of 1907 had 15 students; The first Turkey Day game is played against Kirkwood High School
• 1916 The Echo, Webster Groves High School's newspaper and yearbook, is founded; Tuxedo School is renamed Avery School in honor of the Avery family, early settlers in the community
• 1917 The Webster Groves Armory is converted into the Webster High School Gymnasium
• 1928 Douglass School begins high school classes; it is the only accredited high school in St. Louis County, for African-Americans, until 1954
• 1940 Washington Park School District merges with Webster Groves School District; The "Little Brown Jug" Turkey Day tradition is founded
• 1948 Rock Hill School District merges with Webster Groves School District
• 1949 Clark School opens
• 1951 Edgar Road School opens
• 1952 The "Frisco Bell" Turkey Day tradition is founded
• 1955 Hixson Junior High School (later Hixson Middle School) opens
• 1956 District schools are integrated; Douglass High School closes
• 1958 Warson Woods School opens
• 1960 Plymouth Junior High School and Steger Junior High School open
• 1973 Washington Park School closes
• 1975 Goodall School closes
• 1978 Douglass School closes
• 1983 Steger opens as a sixth grade center; the Webster Groves Computer School opens on the lower level of Steger as a magnet school for children within the district
• 1984 Warson Woods School closes. 1994 American Demographics, a Dow Jones publication, named the district one of nine districts nationwide that produces high-achieving students at a low cost.
• 1996 Statesmen basketball team wins District 4A state championship; President Bill Clinton visits Webster Groves High School to commend the district's drug and violence prevention efforts
• 1997 The district and Webster University establish a formal partnership to pool resources
• 1999 Time magazine devotes a cover story to a week at Webster Groves High School
• 2001 WGSD honored for "Distinction in Performance" by state of Missouri
• 2002 WGSD honored for "Distinction in Performance"
• 2003 WGSD Board of Education honored by MO School Boards Association as "Outstanding School Board"
• 2004 District receives state honor of "Distinction in Performance"
• 2005 District receives state honor of "Distinction in Performance"; Clark School named a Gold Star School
• 2006 District receives state honor of "Distinction in Performance"
• 2007 Avery named a Gold Star School; District receives honor of "Distinction in Performance"
• 2008 Hixson Middle School named a Gold Star School; Statesmen basketball team wins the Class 5 Missouri State Boys Basketball Championship
• District receives honor of "Distinction in Performance"
• 2009 Statesmen football team wins the Class 5 Missouri State Football Championship
• District receives honor of "Distinction in Performance"