The Winn Sisters

Women’s History Month 2021

The Winn Sisters: A family of teachers

Alfred W. and Bertha Hall Winn moved to Kissimmee from Polk County, Florida in 1904 with their four children, Norman, Essie, Grace and Augusta. Their fifth child, Mae, was born a couple of years later.  

Essie Winn Dale, 1958

Essie Winn Dale

The eldest daughter, Loretta Esther “Essie” Winn, was born February 18, 1894, in Highlands City, Polk County.  Following graduation from Osceola High School in 1910, Essie attended Florida State College for Women where in 1911 she was a member of the tennis, Minerva and German clubs. On December 27, 1911, Essie married Harry R. Dale, a native of Texas. Between 1913 and 1925, they had three children, but Essie managed to continue her education, graduating from University of Florida.

Essie began teaching in Kenansville in 1928 and was responsible for three grade levels. She spent 13 years in Kissimmee schools, including four years as principal of Kissimmee Elementary School. She also taught in MacClenny, and from 1947 until her retirement in 1958, Essie was a teacher for the Orlando school system.

In her role as a mother, she served as president of the Parent-Teacher Association. Essie was active in the Florida Education and National Retired Teachers associations, Delta Kappa Gamma and Kappa Delta Phi sororities, a member of First United Methodist Church, and the Woman’s Club. Essie was also a member of the Hart Memorial Library Board and past matron of Kissimmee Chapter of the Eastern Star. Harry passed away in May 1964; Essie died on January 14, 1965. They are buried in Osceola Memory Gardens in Kissimmee.


Grace Winn Makinson, 1960

Grace Winn Makinson

Bertha Grace Winn, also born in Highlands City, entered the world on April 15, 1898. Grace was a 1916 graduate of Osceola High School, continuing her education at Florida State University, University of Florida and Appalachian State Teachers College in Boone, North Carolina. In 1921, Grace became the wife of Henry Nelson Makinson.

By 1930, two children were born to them, a son and daughter. In 1958, Grace was chosen as Beta Sigma Phi’s First Lady of the Year, and the Woman’s Club selected her as their nominee for Teacher of the Year Award in 1959. After serving on the Osceola High School faculty for 20 years, Grace was awarded a certificate in 1959. Upon her retirement in 1963, she was honored at a reception, and the Osceola High School yearbook was dedicated to her for many years of service to the school. During those years, she established the school Thespian Society, serving as director of their productions. Grace also helped structure the Beta Club Scholastic Society.

Grace found time in her busy schedule to be involved in the community, serving as past president of the Kissimmee Woman’s Club, the American Legion Auxiliary and the Florida Education Association. She was a Worthy Matron of the Eastern Star and a Sunday school teacher for 30 years at the First United Methodist Church.

Following her death on November 2, 1990, Grace was laid to rest in Osceola Memory Gardens beside her husband Nelson, who preceded her in death in 1976.


Gus Winn Durrance, 1942

Gus Winn Durrance

Augusta H. “Gus” Winn was born in Highlands City on August 3, 1900. She attended Osceola County schools, graduating from Osceola High in 1918. She received a bachelor’s degree in 1922 from the University of Kentucky and a master’s in education from the University of Florida in 1946. On June 29, 1926 Gus became the wife of Hugh Grady Durrance; a son was born to them the following year.  

During her 33-year teaching career, Gus taught in Kentucky, Miami, Arcadia and Kissimmee, finally retiring in 1961 and returning to Kissimmee. Gus was a member of the National and Kissimmee Retired Teachers Association, the National Education Association, Phi Beta Phi Sorority and held several offices in the Dade County Classroom Teachers Association. She was also a member of St. John’s Episcopal Church in Kissimmee.  

Hugh passed away in 1971; Gus died on February 13, 1980. The cremains of both are interred in Osceola Memory Gardens.


Mae Winn Welbon

Mae Winn Welbon

The Winns’ last child, Mae Ervin Winn, was born on May 13, 1906 in Kissimmee. A 1924 graduate of Osceola High School, Mae attended Hollins University in Virginia and Florida State College for Women. She received a degree from Stetson University, later doing post-graduate work at University of Illinois. A member of Delta Zeta and Theta Alpha Phi sororities while at Stetson, she was also involved with the YWCA Cabinet and various theatrical groups. Like her three sisters, Mae became a teacher.

Mae and William Jay Welbon were wed on June 29, 1939, at First Christian Church in Orlando. Mae taught in Kissimmee, but spent many years as an English teacher in Miami schools. Mae and William moved to Orlando in 1961 where Mae became involved with the Garden Club. William died in 1966; Mae passed away on October 27, 1991. Both are interred in Osceola Memory Gardens.

Written by Anza Bast

Sources:  Ancestry.com; Osceola County Centennial Book; “Kissimmee Valley Gazette” January 11, 1918; “Kissimmee Gazette” June 20, 1958, January 14, 1960, February 18, 1965; “Orlando Sentinel” July 2, 1939, June 5, 1963, February 14, 1980; “News Gazette” February 21, 1980, November 8, 1990, October 31, 1991; Stetson University yearbook online archives