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Sarasota's War Memorial first dedication was held Monday, November 12, 1928. It was part of the ceremony marking the 10th anniversary of the signing of the armistice that ended World War I.

The Sarasota Bay Post of the American Legion built the memorial at the center of Five Points. Designed by area architect Clare C. Hosmer, the memorial incorporated a flagpole placed there in 1917 to honor the Sarasota men who had answered the call to war earlier that spring. The parade for the flagpole dedication began at the Woman's Club (now Florida Studio Theater on Palm and Cocoanut), proceeded to Main Street, east along Main to the railroad tracks (Lemon Avenue) and back to the center of Five Points. Sarasota's band led the parade and the Red Cross auxiliary carried the flag.

The 10th Armistice Day (now Veterans' Day) fell on Sunday. The American Legion celebrated on November 11 by attending the worship service at the Baptist Church. The Sarasota Herald reported that Legion members and auxiliary marched from the Legion home on Golf Street to the church, escorted by the Legion drum corps and the Legion Boy scout troop.

Holiday ceremonies in 1994 included a parade and its' third memorial dedication organized by the Legion. The parade began at Ringling and Main and moved west to Five Points. Two gold-star mothers unveiled the monument and Post Commander Hugh Stevens dedicated it as a tribute to the departed head. A football game between Sarasota High and Bartow High schools concluded the day's events.

In the spring of 1954, the war memorial was moved down Main Street to the Bay Front Park because the State Road Department had declared it a traffic hazard. Fourth of July festivities at the park included a rededication of the memorial, a concert by the Booker High School band and a chicken dinner.

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