Gillespie Day

In 1913 the Sarasota Yacht and Automobile Club declared March 10 as Gillespie Day and promised to celebrate John Hamilton Gillespie with a yearly banquet. Today people might recognize only Gillespie as the name of a park, but the man himself was a fascinating person who is worth remembering. 

The Florida Mortgage and Investment Company, which interestingly was based in Scotland, purchased the land of Sarasota in the 1880s. They designed a nice town with lovely fruit-named streets and convinced more than 50 of their fellow Scots to take the treacherous journey to this new settlement. Unfortunately, when they arrived, they discovered that this beautiful town was only a dream sketched on paper, and many left the wilds of Sarasota for more developed areas. 

Meanwhile, back in Scotland, the president of the Florida Mortgage and Investment Company wanted to salvage this debacle and decided to send his son to Sarasota to save the project. In his early 30s, John Hamilton Gillespie was a well-educated and accomplished man. He was a member of the Royal Company of Archers, was admitted to The Society of Writers to Her Majesty’s Signet and was a captain in the Midlothian Coast Artillery Volunteers. Thankfully, all of these achievements gave him the confidence needed to take on the task that was awaiting him in Florida — a confidence that also radiates through in all photographs of him. 

Gillespie; his wife, Mary; and his golf clubs arrived in Sarasota in 1886. He immediately began making the dream of Sarasota into a reality. As part of his strategy for attracting people to the somewhat desolate area, one of Gillespie’s first priorities was a hotel. The DeSoto Hotel must have been breathtaking to the locals when it was completed in 1887. The three-story structure with an observation deck stood on the bayfront (today the site of the Orange Blossom Towers) proudly welcoming all who came to Sarasota. And because Gillespie could not imagine a civilized society without golf, he also built a three-hole practice course and began to teach the game to his friends.

In 1902 the Seaboard Airline Railroad announced that it would be extending lines south to Sarasota. Having a train come to Sarasota was transformative for the little fishing village and spurred local leaders to incorporate into a town. A hand-drawn seal with the words “May Sarasota Prosper” was created, and the small town elected Gillespie as its first mayor. Gillespie served six nonconsecutive terms as mayor, and locals began to affectionately refer to him as Colonel Gillespie. Even though he was never officially a ranked military colonel, he enjoyed using the name. 

As much as Gillespie loved Sarasota, he might have loved golf even more. He continued to share the game with his friends and in 1904 accomplished his dream of building a nine-hole golf course in Sarasota. The clubhouse stood on what is now the corner of Links Avenue and Golf Street. He also shared this love throughout the state by designing golf courses for the new resorts developing along the railways and writing golf-related articles for newspapers and magazines. It is no wonder that he became known in Florida as the golfing mayor. 

In January 1923, the Sarasota Times wrote a full-page story with the headline, “Founded a Town to get Himself a Golf Game is Story of Col. Gillespie.” At the end of the article, Gillespie shares his philosophy on golf, in which he states, “The real satisfaction in playing golf rests not so much in beating an opponent as in knowing that you played every stroke as it should be played.”    

Gillespie died Sept.7, 1923, in the most Gillespie way imaginable, on his golf course in Sarasota. He is buried in Rosemary Cemetery with his second wife, Blanche. 

The next year, the Sarasota Woman’s Club acquired land from Owen Burns and created Gillespie Park, which to this day continues to remind us of our Sarasota-building, golf-loving, Col. John Hamilton Gillespie, who saw the beauty of early Sarasota and dedicated his life to ensuring that Sarasota prospered. Maybe it is time to reinstate Gillespie Day.

To find out more about Compass Rose History Experiences, please visit our website at CompassRoseHistory.com, or share the love on Facebook or Instagram, @CompassRoseHistory.