Times Square Through the Decades

Ellie Bunting • June 14, 2024

The Tip Top was a popular hangout for teens back in the day.

Introduction

In the past week, I have watched two different presentations on the redevelopment of Times Square. On Tuesday, June 11, the owners of the properties in Times Square presented their plans for the area. On Wednesday, June 12, a group call Resiliency presented their ideas on different projects including Times Square, Old San Carlos, Newton Park, and Connectivity. Both presentations were informative and now residents can provide input into how they see these ideas being implemented. One of the speakers mentioned that this area of the island has always been subjected to change and has been evolving for the better since 1940. The following is a timeline of the development of Times Square and Old San Carlos over the decades.

The Early Years (1910-1940)

The first pier on the island was at the Beach Hotel, built in 1913 and enlarged in the late 20s.

The first bridge to the island was built in 1921. At this time, the Beach Hotel was the only hotel on the island; there were two casinos (Jack DeLyle’s Seminole Sands at the end of Connecticut and Thomas Philips Fort Myers Beach Casino where the Gulf Shore Grill was located). The only road stopped at the Beach Hotel until the late 30s when it was extended to Connecticut; by the 40s, the road was up to the Catholic church. It was not until the 50s that Estero Blvd went to the end of the island. The center of social activity at this time was the Beach Hotel. The road leading from the bridge to the gulf was paved in 1928 and lined with palm trees. There were no businesses along the road until the late 40s and early 50s.

The concrete road from the bridge to the pier lasted until the redevelopment of Times Square in the 90s.

The Fabulous 50s

In 1948, the second fishing pier was built at the north end of the island on property owned by Thomas Philips. The first pier was at the Beach Hotel and was destroyed in the 1944 hurricane. Shortly after the pier opened, the county purchased land north of the pier for a county park.

This was the beginning of what is now called “Times Square.” Once the pier and park were opened, people came to the island to enjoy swimming, fishing, and playing on the beach. These people needed places to purchase beach supplies, food, and entertainment. Businesses began to spout up around the pier and the park. The Tip Top was a popular place for young people to hang out overlooking the gulf. Across the street were more restaurants, arcades, and souvenir shops.

The County Park attracted visitors from all over to enjoy the beach and the pier.

At this time, traffic came off the bridge and took San Carlos Blvd to the pier where it joined Estero Blvd. All traffic had to pass “Times Square” to get on or off the island.

In the 50s, the residents of the island were either business owners, commercial fishermen, or shrimpers. During the winter, snowbirds would come and stay in the trailer courts, cottage courts, or small mom and pop motels. Some would stay for the entire winter and enroll their children in the Beach School. Although we had visitors, I would not say we were a tourist destination at this time.

Garl’s Drug store was an island icon for many years. Mango Bay was in this building when Ian hit in 2022.

Times Square and San Carlos Blvd developed organically as the island grew. With the pier and the county park at the north end, this became the new social center of the island. In 1951, Harold Garl opened Garl’s Drug Store at the corner of Fifth Street and San Carlos. This became the anchor for development along San Carlos.

Soon, this corridor became a true business district. Charles Bigelow opened Bigelow Shopping Center in the early 50s providing another place for businesses to operate.

Bigelow Shopping Center housed many different businesses and was a one stop shop for residents.

The Swinging 60s

The business district continued to grow in the 60s adding more businesses to the corridor. By the end of the decade, four gas stations, a furniture store, a full-service grocery store, several motels, gift shops, a doctor’s office, a beauty salon, a cocktail lounge and many real estate offices were opened along San Carlos Blvd and in Bigelow Shopping Center.

The intersection of San Carlos and Estero was made one way in the 60s.

At some time in this decade, the traffic pattern was changed to allow traffic to flow onto Estero without going around Times Square. After getting off the bridge, you would continue on San Carlos Blvd until the road split near Winds. If you wanted to visit Times Square or the other businesses on San Carlos, you would continue straight on San Carlos. If you wanted to get onto Estero, you would bear left avoiding Times Square completely.

San Carlos Blvd was the business district for many years until the new bridge was built in 1979.

Sensational 70s

This decade brought many changes to the island. The biggest change was the addition of a new bridge in 1979 which changed the island in many ways. Residents were thrilled with the idea of a new bridge since the old swing bridge was on its last legs and was being blamed for all the traffic issues. The new bridge would eliminate those problems. When the new bridge opened, everything changed in the “downtown” area of the island.

The Sky Bridge brought many changes to the island, but it did not improve the traffic issues as we hoped it would.

The new bridge went over most of San Carlos Blvd and dumped traffic directly onto Estero. Residents and visitors no longer needed to pass all the business that were along San Carlos. New businesses such as a Pizza Hut and a Kentucky Fried Chicken had opened next to some of the older businesses.

To visit these businesses, you had to turn right on Fifth Street and then go back onto San Carlos or forward to Times Square.

The 70s were also a time of growth on the island as the first condos were built in the late 60s so by the 70s developers were quickly buying up the old motels, hotels, and cottages, and replacing them with high rise condos.

By the 70s, the county park had many amenities such as a bath house, playground, and picnic tables.

Electric 80s

The building frenzy of the 70s continued into the 80s with 68 new condo complexes being developed. Unfortunately, this growth did not help the businesses along San Carlos and in Times Square. The change in the traffic pattern caused the deterioration of these areas.

The change in the traffic pattern allowed people to drive around the Times Square area without going down San Carlos Blvd. Mostly young people (me included) liked to get in their cool cars, roll down the windows, blast the music, and drive north to Times Square. They would turn onto Fifth Street and then turn left to go around Times Square where they would “check out” what was going on. If they did not stop anywhere, they would make the loop again. This would happen all day and all-night causing traffic to back up (or so they said).

This is a good shot of San Carlos before the redevelopment of Times Square.

As early as 1987, the News-Press ran an article proposing a pedestrian mall around Times Square. If cars were not allowed to drive down San Carlos to Estero, they could eliminate the loop problem. Although the idea was floated around, nothing really happened until the 1990s.

In the mid 80s, Tom Myers built Seafarers Village at the corner of Estero and San Carlos. The small mall was home to many different businesses including a fancy restaurant, a great deli, a liquor store, and other small gift shops.

Nifty 90s

The 90s was a decade of change in many ways. The high-rise condos continued to replace the cottage courts and motels. The “downtown” area continued to deteriorate as the business that once provided services for residents packed up and left the island. Pizza Hut, Kentucky Fried Chicken, Dockside Pizza, the car wash, and more were gone and the area was considered “blighted.”

In 1994, the idea of a pedestrian mall came up again. At first the idea was met with resistance from the business owners fearing that without traffic going past their establishments, they could not survive. After much discussion, the county decided to try the pedestrian mall idea and then decide whether to make it permanent.

The redeveloped Times Square became a pedestrian mall which eliminated the “looping,” but didn’t help the traffic.

By 1996, Times Square was a pedestrian mall, and most people were on board with the idea. When the town incorporated in 1995, they began working with the county on the redevelopment of San Carlos Blvd and Times Square.

Ground was broken on the new Times Square in 1996 after much discussion and planning. Once the project was completed, businesses in the area started to recover as residents and visitors came to enjoy the new entertainment district.

The new sidewalks, underground lighting, colorful bricks and eclectic buildings made the area funky and there was definitely a beach vibe from the gulf to the bay.

Everything was going well until 2004 when Charley came to visit.

Trendy 20s

Before August 2004, the last hurricane to hit Fort Myers Beach was Hurricane Donna in 1960. Since that time, the island had developed quite a bit with many high rises and more permanent residents. Charley was a smaller storm than Ian and the damage on the island was not nearly as bad as it was in Ian. However, there were some structures that sustained quite a bit of damage and needed to be taken down.

This was the Tip Top after Hurricane Donna in 1960.

By the time Charley hit, the newly designed Times Square and Pedestrian Mall had been completed. After the storm, the town planning continued. The next step in the process was to work on the Estero Blvd Street Scape plan that was part of the original redevelopment process.

In 2004, Dave Meyers purchased Seafarer’s Mall and three other parcels on the gulf side of Estero going from the Sandman Motel to Canal Street. A short time after he made this investment, Hurricane Charley caused major damage on the island, pretty much destroying Seafarer’s Mall and damaging these hotels.

In 2006, Meyers presented a proposal to tear down Seafarer’s Mall and replace it with 65 hotel units and a 220-space parking garage. An investment group known as Time Square FMB was planning to develop this section of the island, but in 2010, they were facing foreclosure. By 2013, the town council and Lee County were in discussions regarding the future of this property. The damaged mall and run-down hotels were considered a blighted area, and the town and the county knew something needed to be done. After much discussion, the county agreed to purchase the land that was home to Seafarers, the Sandman Motel, Howard Johnsons, and Days Inn. Using Tourist Development funds, 5.6 million was paid for the property that was to become a beachside park.

Hurricane Ian destroyed Times Square as plans for its redevelopment continue.

In 2016, TPI Hospitality led by Tom Torgenson, began plans to develop a several large parcels of land on both sides of Estero. Torgenson and his group faced many challenges and oppostions before construction began in August 2021. Hurricane Ian destroyed over 90 percent of the buildings on the island when it hit on September 22, 2022. Although Margaritaville suffered some setbacks, the resort rebounded quickly and opened in December 2023. Despite all the complaining and setbacks, most residents saw the new resort as a beacon of hope for the devastated community.

We are now approaching the second anniversary of Hurricane Ian. Residents and visitors have continued to be drawn to the Times Square area, and it has once again become the social center of the island. As the presenters explained their ideas for the new Times Square, they made it quite clear, that we cannot rebuild the area they way it was. Setbacks and other federal building regulations need to be taken into account in this rebuild.

Now is the time for public meetings and discussions. This was done back in the 90s and was a good way for everyone to provide input. Let’s hope we can come together and support these business owners who are trying to get back on their feet.

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The Gullah Heritage: From Sea Islands to Florida

By Ellie Bunting • December 27, 2024

In January, the speaker for Estero Island Historic Society’s public meeting will be Martha Bireda, director of the Blanchard House Museum of African American History and Culture of Charlotte County. Ms. Bireda is the great-granddaughter of Queen Evans Andrews, a pioneer who came to Punta Gorda in 1897 from Charleston, South Carolina. She will share stories of the Gullah culture and of her visits with the Gullah people who live on James and Johns Islands. Having just visited the Georgia and South Carolina Coasts, I thought this might be a good time to do a bit of research into the Gullah culture in anticipation of our January meeting.

1921 Tampa Bay Hurricane

By Ellie Bunting • October 8, 2024

Repairing the St. Pete pier after the storm. Florida Archives. As we prepare to run from another hurricane, it might be helpful to reflect upon the 1921 “Tampa Bay” hurricane which hit the Tarpon Springs/Tampa area on October 28, 1921 This was the first major storm to hit the Tampa area since the “Great Gale” of 1848. We can draw a few parallels between this hurricane and what we are now facing with Milton. In 1921, the weather forecasting was not what it is today; rather, the forecast was based on observation sites which reported breezy and cloudy conditions around a low pressure system that was organizing off the coast of Honduras on October 20 and 21. By October 22 and 23, the area of low pressure began to intensify. Winds reached tropical storm force at the observation sites. The sites reported thunderstorms and cloudiness across the Caribbean.

Labor Day Hurricane 1935

By Ellie Bunting • September 1, 2024

Searching for survivors on Upper Matecumbe Key after the storm. Photo Credit: Creative Commons In the late summer of 1935, the citizens of the Florida Keys were in the depths of the Great Depression. Key West, once a prosperous port city, had declared bankruptcy. Residents were struggling to live on an average monthly income of $7. The city needed a plan to survive so it was decided to rehab the old buildings and re-create Key West as a tourist destination. The government saw this as a way to help the jobless World War I veterans who had been affected by the economic downturn. The vets would be paid $30 a month plus free room and board to come to the Keys and build the bridges and roads that would be needed to support the Key West plan. The men were housed in flimsy shacks built on the shoreline. Residents of the Keys warned that this housing would never survive a hurricane, but their warnings were not heeded. The government plan in case of a storm was to send a special train from Miami to evacuate the vets if a storm approached. Like many plans, this one was not thought through very well. The railroad officials insisted that they would need several hours of lead time to get a train ready and on its way to the Keys. It was in late August 1935 that a tropical wave came off the coast of Africa heading across the Atlantic towards the Caribbean. At this time, predicting storms was not a science. With no satellite images or hurricane hunter planes, meteorologists were pretty much shooting in the dark with only a newly developed radar to help them predict when or where a storm would hit.

Who Was Jack DeLysle?

By Ellie Bunting • September 1, 2024

Who was Jack DeLysle? I had been reading about him in different articles as I was doing research on the early days on the island. I had come up empty except for one cryptic note I found that he “left the island under mysterious circumstances.” Yesterday, I was going through copies of the Sand Paper that were donated to the historic society and found an article by Jean Matthews that was about Jack DeLysle. This is what I learned about the mystery man who played a pivotal role in the early development of the island. Jack and his brother, John, first appeared in Southwest Florida after their ship ran aground at the moth of Gordon’s Pass. When Sheriff Frank Tippins arrived to investigate the incident, he found 320 boxes of “Soap” that turned out to be whiskey. The brothers had apparently picked up the moonshine in Alabama and sailed to Tampa, then Key West, and finally to Cuba. When they returned to Florida, they were caught in a storm and the ship was wrecked. “Captain” Jack DeLysle claimed he was in the British Army; however, he and John were arrested and turned over to the Feds. Both men were found innocent by a jury in Tampa and Jack returned to Fort Myers where he was into many different endeavors. Although he wrote poetry that he published in the local paper, DeLysle is best known for his efforts to raise money to build a bridge to Fort Myers Beach. He joined the Crescent Bridge Road Company where he met E.E. Damkohler. Damkohler was trying to raise money to build a road from Miner’s Corner to the Island. DeLysle saw potential in Crescent Beach ( old name for Fort Myers Beach)being developed into a tourist mecca like Miami Beach. He purchased property in Case Subdivision and built the Seminole Sands Casino. DeLysle’s casino had a game room with tables and slot machines, changing rooms, a dance pavilion, and a restaurant.

Al Capone and FMB?

By Ellie Bunting • July 3, 2024

Did Al Capone spend a week on Fort Myers Beach back in 1929 or 1930? According to Jean Matthew, Capone and some of his lawyers may have stayed at the home of Dr. Baker Whisnant in Seminole Park. The group consisted of two attorneys and their families, including their children, and of course, Mrs. and Mrs. Capone. Matthews states that the two lawyers who were with Capone rented a beach cottage at the same time they rented the home in Fort Myers. Rumors began spreading around town that Capone and his gang had been seen hanging round in downtown Fort Myers. The cook who worked at the Seminole Park house while the gang was staying there stated that every morning a strange man would appear and eat breakfast at the house, arriving from the beach. Was this mysterious stranger really the infamous Al Capone? The cook’s description of the man sounded like Capone who also had a deep scar on the left side of his face. The strange man never went out during the day. He would stay home and play with the children until evening when he would leave. Other people in town also recall this stranger who may have been the famous gangster. A young gas station attendant who was working at the Standard Oil station on McGregor waited on the stranger. When he was caught staring at the gangster, Capone is reported to have told him, “You know who I am, but kept it under your hat.” Mrs. Whisnant, the owner of the Seminole Park home, said that the group acted strange from the beginning. They didn’t register at a hotel. They immediately sought out the realtor who was in charge of the rental and were brought to the home immediately. They took only a brief time to look over the house before asking to move in in immediately. They didn’t want a phone. They asked about the mail but insisted that their business was all transacted by telegraph. When the group left, and the owner was cleaning up her house, she found many cases of empty liquor bottles. The residents of Seminole Park told her that the renters were not very friendly and stayed to themselves. After reading this in the Sandpaper, I decided to do a bit more research to get to the truth about Al Capone’s visit to Southwest Florida.

Hurricane Season is Upon Us: Predictions

By Ellie Bunting • June 3, 2024

As we are all still recovering from Hurricane Ian, the news from NOAA that was released this week is a bit intimidating. Forecasters estimate 17- 25 named storms this season with 8-13 reaching hurricane strength. Of these, forecasters predict that 4-7 would be considered “major.” This is not great news, and it gets worse. Florida has a 96% chance of being impacted by one or more of these named storms. If we look at only hurricanes, the probability of a hurricane hitting the sunshine state drops to 75%. This drops even more to 44% when we look only at a ‘major’ hurricane hitting our state.

Preserving Our Environment: The Battle for Estero Bay

By Ellie Bunting • May 7, 2024

While doing research for Lost Icons, I came across a quote in the News-Press that I have cited several times in other articles and presentations. Written in the late 1970s, this quote seems to bring the past and the future together quite nicely: “Nobody really wants to stop progress, but there is an increasing awareness that the island is in danger of becoming a polluted paradise.” Over fifty years ago, the paper stated that Fort Myers Beach was at a crossroads. The 70s were a time of rapid, uncontrolled development with over 68 condos being developed in a single decade. This led residents to vote to incorporate the town so we could control our own destiny and stop the over-development of our island. The newly born town elected its first town council who worked very hard to create a comp plan that would guide our development and preserve our island lifestyle. This plan was completed in 1995 and had served us well until Hurricane Ian damaged every building on the island. Now that we are in the rebuilding mode, we are once again at a crossroads: Do we stick to the comp plan and turn down the developers who want to build higher and bigger? So far, the council has been carefully considering all arguments and is making logical decisions trying to keep as close to the comp plan as possible. The council and residents need to tread carefully to make sure, in our efforts to build back, we spend time anticipating the unintended consequences of building back bigger. One very good example of this is the recent attempt of two legislators to take back 225 acres that are part of the Estero Bay Aquatic Preserve. (More on this in another post). This was not the first time our beautiful back bay was threatened. Let’s go back to the 1960s when a group of concerned residents decided to take action to preserve the beauty of our back bay. Back to the Future

Home Buying Today

By Ellie Bunting • April 27, 2024

Is It Getting More Affordable to Buy a Home? Over the past year or so, a lot of people have been talking about how tough it is to buy a home . And while there’s no arguing affordability is still tight, there are signs it’s starting to get a bit better and may improve even more throughout the year. Elijah de la Campa, Senior Economist at Redfin, says : “ We’re slowly climbing our way out of an affordability hole, but we have a long way to go. Rates have come down from their peak and are expected to fall again by the end of the year, which should make homebuying a little more affordable and incentivize buyers to come off the sidelines.” Here’s a look at the latest data for the three biggest factors that affect home affordability: mortgage rates , home prices , and wages. 1. Mortgage Rates Mortgage rates have been volatile this year – bouncing around in the upper 6% to low 7% range. That’s still quite a bit higher than where they were a couple of years ago. But there is a sliver of good news. Despite the recent volatility, rates are still lower than they were last fall when they reached nearly 8% . On top of that, most experts still think they’ll come down some over the course of the year. A recent article from Bright MLS explains : “ Expect rates to come down in the second half of 2024 but remain above 6% this year. Even a modest drop in rates will bring both more buyers and more sellers into the market.” Any drop in rates can make a difference for you. When rates go down, you can afford the home you really want more easily because your monthly payment would be lower. 2. Home Prices The second big factor to think about is home prices . Most experts project they’ll keep going up this year, but at a more normal pace. That’s because there are more homes on the market this year, but still not enough for everyone who wants to buy one. The graph below shows the latest 2024 home price forecasts from seven different organizations :

Treasure and Dead Bodies

By Ellie Bunting • April 26, 2024

Did WC Zimmerman Discover a Lost Treasure on What is Now San Carlos Island? Although I really enjoy researching and writing about local history, I am also a sucker for local legends and lore, so when I was given an article taken from a 1897 issue of a newspaper called Fisherman and Farmer, I knew I had to do a deeper dive.

Fort Myers Beach Fire Department Has a Long Successful History

By Ellie Bunting • November 10, 2023

I have been reading recently about the plan to merge the FMB Fire Department with Bonita. I am by no means an expert on how or if this would be a money saving move, but I do know that the FMB Fire Department has been the pride of our island since 1949 when the Beach Volunteer Fire Department was born at “Jenk’s Bar” on San Carlos Island. Twenty-two men attended the banquet meeting. Earl Howie was the first Fire Chief, and J. Travis Cowart was elected Fire Captain. This was the beginning. Prior to this time, there was no established fire department on the island, and the closest fire apparatus was 20 miles away in Fort Myers. The information in this article comes from a small booklet written by former Chief John McCarthy called simply “The History of the Fort Myers Beach Fire Department.” After raising funds from the island residents, the new department purchased a small two-wheeled spray pump, tank, and trailer that was pulled by a borrowed jeep (McCarthy). These were housed at Red Coconut. Residents could call the department by dialing 2541, a precursor to 911. In April 1950, an old international war-surplus fire/rescue crash truck was purchased. This was a step up from the original truck and was the first real fire apparatus that the department owned. It lasted until May 1964 when it was sold to Leigh Acres Volunteer Fire Department.