01/21/2026
Esther Haile Connolly
There are few of us in my generation who have lived in Monticello for many years that do not remember Ms. Esther. To put it mildly, she was a force.
Esther Haile Connolly was born in Monticello, Florida, on October 4, 1897, the daughter of William Edward Haile and Addie Lawrence Tatum Haile. Her maternal great-grandparents Andrew and Adaline Denham were married in Monticello in 1836.
Mrs. Connolly attended private and public schools in Jefferson County, graduating in 1914 from the Jefferson Collegiate Institute in 1915. She entered Florida State College for Women (now Florida State University) graduating in 1919 with a LI degree from the normal school and a BA from the college.
After teaching English and history several years in Monticello and Quincy, Mrs. Connolly moved to Washington, DC in 1922 where she served as a teacher and assistant librarian in the Department of Occupational Therapy at Walter Reed Army Hospital. In 1926 she married Frederick Connolly, and after his death in 1947 carried on his insurance business in Washington until she retired. Mr. Connolly was raised in Gainesville, Florida.
During Mrs. Connolly‘s years in Washington, she was an active member of the Garden Club of Chevy Chase, Maryland, the National Trust for Historic Preservation, the Georgetown Citizens Association, the National Society of the Colonial Dames of America in the District of Columbia, the Board of the Washington City Orphan Asylum (later called Hillcrest children’s village), and the women’s board of the Washington Symphony Orchestra
Mrs. Connolly’s hobbies over the years were history, old houses, historic preservation, gardening, and travel. She was a member of the Monticello Presbyterian Church.
When she returned to Monticello in 1963, she had been active in many local civic organizations. She was a charter member of the Jefferson County Historical Association and had been its president over a period of 10 years. She was active in helping produce the annual tour of homes. She also assisted in the survey of Jefferson County resulting in the establishment of a historic district in Monticello and the listing of many buildings in the national register. She obtained funds to repair graves in the Old Monticello Cemetery, the Palmer family cemetery and the old Bailey/Bellamy cemetery.
As a member of the Monticello Woman’s Club Civic Committee, Mrs. Connolly headed the drive to secure a regional library for Jefferson County. As a member of the Monticello Garden Club, she was active in the planning and preservation of trees on our city streets. —Info from a Watermelon Festival program dated before 1994
I have a personal memory of her—one handed down by my father. In the early 1970s, while I was away at college and Dad was trimming trees to help keep me there, he ran into Mrs. Connolly one afternoon. She stopped to ask who had given him permission to take down a particular tree. Dad explained that it was diseased and had been dropping limbs onto Mrs. Winans’s house.
Mrs. Connolly ordered him to stop at once and come down. Moments later, Mrs. Winans came out of her house, and the two women launched into a heated argument beneath the oak tree on West Washington Street.
Dad recounted the incident to Mom later that day, and I remember her asking where he had been during the dispute. “I stayed in the tree,” he said. “There was no way I was getting between those two headstrong women.”
Ms. Esther died in 1994 at the age of 97, and she is buried next to her husband in Arlington National Cemetery.