On The Chisholm Trail features silhouettes of a herd of longhorn cattle moving over the Chisholm Trail from their home ranges in south Texas to shipping facilities in Abilene, Kansas. The lone Native American shown in this piece represents the “toll taker” who granted free passage through Indian territory in exchange for two or three “wohaws.” The sketches for this piece were provided by Enid-born artist Harold Holden. The monument and silhouettes were dedicated and donated to the City of Enid on September 27, 2003.