08/12/2026
1905 — A Gala Day in Fort Myers
While looking through the collections at the Southwest Florida Historical Society, Joanne Iwinski Miller, came across this wonderful old image and wanted to share it, along with a little information about the event it advertised. Written on the back of the photograph are the words: “Bay Street, Fort Myers.” Could that be the Heitman Brick building on the left?
Imagine Fort Myers in 1905, when a real estate auction wasn't simply a sale—it was an all-day community celebration complete with a military band, free carriage rides, a balloon ascension, a parachute jump, and even a high-diving dog!
On Tuesday, March 7, 1905, the Fitzsimmons Auction Company announced the sale of 150 building lots in W. H. Towles' (Evans) South-Side Addition. The advertisement promoted the property as being "within the residential future of Greater Fort Myers," and the lots were to be sold to the highest bidders.
Buyers didn't even need to have all the money up front. Terms called for one-fourth cash, with the balance payable in six, twelve and eighteen months at six percent interest.
But selling land was only part of the attraction.
The day was advertised as a "Gala Day of Fun & Fortune." A Fort Myers military band was scheduled to perform in the business district from 8:00 to 9:00 that morning. At 9:00, a grand parade of free carriages would leave the business center and carry prospective buyers to the auction.
Then came the entertainment.
Professor Bonansinga was advertised to ascend thousands of feet into the air in what was described as the largest hot-air balloon in the world—and then make a parachute leap back toward the ground.
As if that weren't enough excitement, "High Diving Dewey," billed as the highest-diving dog, was to make a 50-foot plunge from a mid-air pedestal during the sale.
There was even a free lot drawing. Everyone attending could enter, and according to the advertisement, "Somebody must draw it. Everybody can try."
At 9:30 a.m., Col. W. W. Bishop, described in the colorful language of the day as America's "200-pound bundle of wit, wind and wisdom," was scheduled to open the auction.
The advertisement gives us a wonderful glimpse into the optimism surrounding Fort Myers at the beginning of the 20th century. Promoters called the town "The Gateway to Eternal Paradise" and promised that its growth would bring increasing real-estate values and a golden future.
The sales pitch was certainly enthusiastic:
"The growth of a day will make Dollars for every Penny invested."
One sentence in the advertisement, however, is a stark reminder of the racial discrimination of the era. The promoters specifically advertised the event as "purely a white-man's sale." It is an uncomfortable phrase today, but an important part of the historical record, illustrating how segregation and racial exclusion were openly incorporated into real-estate promotion in early Fort Myers.
More than 120 years later, this old image and advertisement give us a fascinating window into Fort Myers during a time when the town was still small but promoters were already dreaming about its future.
In 1905 Fort Myers, you didn't just attend a real estate auction.
You brought the family, listened to the band, rode in a carriage, watched a balloon rise into the Florida sky, witnessed a parachute jump and a high-diving dog—and perhaps went home owning a little piece of the future of Fort Myers.
Joanne Iwinski Miller 2026