It has been called the oldest continuously operating boarding school in the South.

[1] As expressed by William R. Webb, the school's mission is "To turn out young people who are tireless workers and who know how to work effectively; who are accurate scholars, who know the finer points of morals and practice them in their daily living; who are always courteous [without the slightest trace of snobbery]."

(Bracketed text was removed from the official mission of the school in the late 20th century but is commonly added to oral recitations by faculty and students.)

[1] After Vanderbilt University was founded in 1873, Webb School's "oldest and best boys" were able to enroll.

[1] Webb moved the school from Culleoka to its present-day location, a 145-acre campus in the small town of Bell Buckle, in 1886 after Culleoka incorporated and legalized the sale of alcohol in the new city.