It was 1956 when Jo Cortes, editor of Englewood’s first newspaper, The Englewood Herald, originated the idea of Pioneer Days. She felt it would

stir up a little excitement in the then tiny town. And she was hoping to create a bit of economic input from outside visitors for local merchants.

Cortes said she choose the hot, dog days of summer for the events because they were the low point of the year, and it was at this time the town needed a little stimulation. The concept still holds true.

When the local celebration was first started it was planned for the third week in August, tying in with the founding of the town of Englewood, which was plated August 17, 1896. Later the date was changed to coincide with the Labor Day Weekend. Cortes was in great awe of the pioneers who carved out a life from the wilderness here in our area, and at the same time, the town of Englewood.   Naming the festivities Pioneer Days was her way of honoring them. At the first Pioneer Days the guests of honor were twelve true pioneers. All but one had come to Englewood prior to 1900. That idea has evolved into naming a grand marshall of the parade each year who is usually from one of the old families of Englewood.

The first Pioneer Days were billed, by Cortes, as the biggest midsummer celebration in Florida. That probably was not a total untruth. Undoubtedly, it was one of the very few events taking place through out the state during the worst part of the year, weather wise. Cortes’ plan to give a commercial boost to the town at the slowest time of the year worked. People came from all around for the festivities bringing with them spending money. Aside from that, local residents all got involved and great fun was had. A lot of attention was given to planning events that the local young people could participate in and enjoy.

Hats, Races & Beauty Contests

Pat Smith grew up in Englewood and remembers the early Pioneer Days. “Pioneer Days was always a real joint effort, everyone pulled together. The clubs that helped put on the events asked you to buy a Pioneer Days Hat and if you bought one then there was no charge to any event. Talking about how everyone in town participated Pat recalled the early Miss Pioneer Days and Miss Englewood contests. “All the girls entered the contest no matter who she was just to show community support. It was supposed to teach you modeling and poise and how to meet people and be a better spokeswoman for Englewood. There would be 30 or 40 girls in the contest--just about every girl in town.”
Fondly remembered by Pat was another event she was in, the Pram Races. These were tiny sailboats manned by children. “The Pram Races were always an important Pioneer Days event. They were held in view of the bridge (now the Bill Anger Fishing Pier) because that was the main viewing point for the spectators for all the water events. Invariably there would be no wind that day and the parents would agonize over watching us sit dead in the water.”  Other water events included a decorated boat parade with prizes for the best decorations, swimming races, water ski shows, family runabout boat races. The big draw was the sanctioned American Power Boat Association boat races. All these events could be viewed from the bridge because this was before the Intra Coastal Waterway was dug and there was no boat traffic.

The Parade & The Shipwreck Dance

Onshore there was the parade that included floats, all home made in those days, and a segment which was nothing but bicycles decorated by and ridden by kiddies. Cortes billed it “The Largest Bicycle Parade in Florida.” There was a crazy hat contest, a beard contest, san amateur night and dinners. One of the most fun events was the shipwreck dance held at Whiskey Corners, which was demolished when Merchants Crossing was built. Bernie Reading remembers the first dance well as he served as the emcee. “You had to come dressed as if you were a shipwreck victim. Everyone was dressed in a ridiculous manner and really let their hair down. People got a kick out of seeing a lot of upstanding figures of importance in the community acting silly and having such a good time. It was a lot of fun.”

Many thanks to Diana Harris for writing this charming article about Pioneer Days.  You can contact Diana Harris at This e-mail address is being protected from spambots. You need JavaScript enabled to view it