How a Tenacious and Visionary Scot Guided Sarasota Through its Early Days

Scottish flags flying at the border crossing from England to Scotland


By Maxwell Martin


Back in 1884, Sarasota was described as having Florida’s best hunting and deep-sea fishing and weather for growing citrus. In addition, it was touted as not only a great winter vacation spot for northerners but also as a wonderful summer locale for southerners. The latter were presumably better adjusted to the heat, humidity, and ubiquitous mosquitoes of Florida’s summertime in the era before air conditioning and bug spray.

Not surprisingly, given Florida’s long history of ballyhooing tourism and growth, the aforementioned claims were made by Florida’s State Engineer, Captain H.S. Duval,  in a December 28, 1884 report to the Florida Mortgage & Investment Company.

Based in Edinburgh, Scotland, the company wanted to start a Scottish settlement of about 200 families on 47,000 acres of Sarasota area land that it had purchased from the State of Florida. The Scots were particularly attracted to this area not only because of Captain Duval’s claims but also because of real estate promoters’ advertisements, which were widespread in Scotland at the time.


View of Edinburgh, Scotland, ca. 1890. Courtesy of Library of Congress.


Here’s what the company offered – a deal that today’s real estate shoppers perusing Sarasota’s pricey property would envy: For 100 Pounds Sterling, each family that agreed to settle in Sarasota would be given 40 acres of land to farm, plus a lot in the town. The goal was to grow citrus on the acreage and build a house on the lot.

After traveling from Edinburgh to New York and finally down to Florida, the Scots soon figured out that their newly founded settlement, which was dubbed “Ormiston Colony,” presented lots of challenges. For one thing, the land was an unforgiving wilderness in which swarms of mosquitoes “traveled in black clouds.”

Those were just some of the problems that the settlers encountered. They also learned that the road to prosperity in Sarasota had more potholes and other obstacles than the colonists had been led to believe. Indeed, the Scots now understood why they received such a great deal.

As for Sarasota’s earliest Scottish settlers, nothing seemed to be working out. They were able to build six cottages on Main Street, but everything else was heading to despair. Their lack of knowledge of the soil conditions was impeding their ability to grow citrus, and the crops they did manage plant in their fields were periodically washed away by storms. To add insult to injury, their first winter in this tropical hinterland featured freezing weather and a rare dusting of snow.


City dock and lower Main Street in Sarasota, Florida, ca. 1888. Courtesy of Florida Memory


The Ormiston Colony’s settlers were truly on their own. Early on they didn’t even have a marketplace to buy and sell goods. In fact, the nearest market was located in Manatee, a town some 15 miles away via primitive trails that were largely impassable.

For most of these Scottish pioneers, the Sarasota colony was a major investment of time and money without little reward, and some were becoming discouraged. Several families even left. One of them, the Lawries, packed up and moved to New York, calling the colonists a “disillusioned bunch.”

Worse, the man who directed church every Sunday had to flee with his family because some of the colonists were shooting at his house. The demise of the Scottish colony finally seemed imminent, Sarasota itself was on the verge of collapse, and something obviously needed to be done.

When Florida Mortgage & Investment Company got wind of what was going on at its “Little Scotland” settlement, company officials decided to take action. Due to their steadfast efforts, the Ormiston Colony would finally be on the verge of becoming the City of Sarasota.

That’s because the Florida Mortgage and Investment Company dispatched a man named John Hamilton Gillespie to Sarasota. Now credited as “the Father of Sarasota,” he was then a co-manager of the company. When he arrived in March of 1886, the settlement was on the brink of ruination.


John Hamilton Gillespie posing under a large palmetto in Sarasota, Florida, ca. 1901. Courtesy of Florida Memory.


Gillespie wasn’t your typical developer. He had served Queen Victoria as a body guard and was a member of the Royal Company of Archers. More importantly, it turns out, he absolutely loved golf. He was a longtime member of Scotland’s famed St. Andrews course, and he imbued his passion for game into the development of Sarasota. Not surprisingly, given Gillespie’s enthusiasm and impressive background, the floundering settlement’s morale quickly changed.

Gillespie got the atrophied settlement moving forward by getting much-needed supplies and workers. The downtown was the first area Gillespie developed. He built the Sarasota House and a boarding house at Five Points, which is still a key intersection in the heart of present-day Sarasota’s downtown.


Ariel view looking over the Five Points area of downtown Sarasota, Florida, January 1941. Courtesy of Florida Memory.


Pursuing his passion for golf, he immediately created a two-hole golf course on what is now Sarasota’s Main Street. Gillespie’s course featured one long fairway with two greens, one on each side of the fairway.

Gillespie’s modest layout was credited with being among the first golf courses in the United States, and settlers reported that Gillespie could be seen on his golf course for many hours every day. Sarasota resident Alex Browning was with Gillespie on the golf course one day and was asked if he had ever played golf. Browning, who had no knowledge of golf, said he had not, to which Gillespie reportedly responded, “Mon, y’re missin’ half ye life.”

Although Gillespie created this golf course mainly because of his own love for the game, he also saw it as a potential tourist attraction, along with the beaches and the new DeSoto Hotel, which opened in February of 1887.


The DeSoto Hotel in Sarasota, Florida, ca. 1887. Courtesy of Florida Memory.


Unfortunately, Gillespie soon found that his ultimate goal of Sarasota as a tourist Mecca for the wealthy was several decades premature. For one thing, the number of guests required to sustain the hotel wasn’t feasible at the time. As a result, the hotel was shuttered from 1899 until 1902, when it was then sold to Southern Investment Company.

A bigger problem for Gillespie was figuring out how to boost the area’s population. As of 1897 there were still only 200 or so permanent residents. Moreover, Sarasota remained sequestered in the Florida wilds.

Not only did the area lack passable roads, but there wasn’t a rail line that linked it to any major city. Instead, Sarasota’s trade and tourism  depended on a steamship based in Tampa.

Due to the settlements location, Gillespie quickly realized that boosting tourism was the surest way to build the kind of sound economic foundation necessary to support the permanent residents and growth. First, however, he would have to resolve the lack of convenient transportation so tourists could travel to and from Sarasota.

Gillespie decided that he wanted to develop a railroad system to connect Sarasota with Tampa and, thus, with the rest of the country. He was quoted as stating that “the country would know greater prosperity if there were less distrust of railroads.”


View of lower Main Street from roof of the DeSoto Hotel in Sarasota, Florida, ca. 1887. Courtesy of Florida Memory.


His first attempt, dubbed “The Slow and Wobbly,” was financed by the Florida Mortgage and Investment Company in 1892. The rail line went from Bradentown (now Bradenton) to Sarasota, and was supposed to connect with the steamships based in Tampa.

Unfortunately, because these trains attracted only a small number passengers, “The Slow and Wobbly” lasted for only three years, an episode the residents of Sarasota dubbed “comical.” Gillespie knew full well that better train service would be needed in order to attract more tourists and residents.

So Gillespie persisted with his efforts to obtain better railroad access, and in 1902, a deal was reached to establish more efficient train service to Sarasota by the following year.

Indeed, 1902 was a big year for Sarasota and for Gillespie. With a better rail connection promising to spur growth, the residents decided to incorporate Sarasota as a town. That October, Sarasota elected John Gillespie as the new town’s mayor.

Mayor Gillespie served several terms – from 1902 to 1907 and again from 1909 to 1910. The citizens also chose “May Sarasota Prosper,” which sounded like a prayer, as the town’s official motto.

Finally, on March 22, 1903, the railroad line linking Sarasota to Tampa was completed by the United States and West Indies Railroad and Steamship Company. This  ended Sarasota’s isolation, but for some reason the tourists and newcomers were still lagging behind expectations.

Gillespie, undoubtedly still confident in his town’s future prospects, nonetheless carried on with additional ambitious improvements to the area’s infrastructure as well as with the beautification of Sarasota’s downtown.


View of Sarasota, Florida in 1924. Courtesy of Florida Memory.


There were several especially noteworthy improvements that Gillespie made after the railroad line arrived. For one thing, he thought it would be important to have a bank in Sarasota. Manatee was the closest town with a bank.  Although it was a mere 15 or so miles away, highway travel was still a challenge.

To attract a bank, Gillespie began conversations with T.C. Taliaferro, President of both the National Bank of Tampa and the First National Bank of Manatee. After reviewing Gillespie’s request, Taliaferro said he would start a bank in Sarasota – but only if Gillespie constructed a bank building worthy of Taliaferro’s dignified taste.

Gillespie did not disappoint. He built Sarasota’s first structure made of concrete; the sand and cement mix later became a staple of Florida architecture. The building was named after him and not only housed the bank but also Gillespie’s office and a library to which he donated myriad books.

Similar architecture continued during this era of Sarasota’s development. One of the more notable of Gillespie’s building’s was the Halton Sanitarium, later known as the Halton Hotel.

Because Sarasota’s “salubrious climate” was one of many reasons advertisers cited in an effort to lure people there, the Halton Sanitarium was promoted as a place for tourists to get healthy while enjoying amenities such as tennis, boating, and fishing.

As Sarasota grew and became economically more self-sufficient, there was no longer a need for the Florida Mortgage and Investment Company. Therefore, in March 1908, all of the company’s remaining assets in that area were given to Gillespie for the continued growth and prosperity of Sarasota.

A.B. Edwards, who in 1914 became the City of Sarasota’s first Mayor when the municipality officially transitioned from a town to a city, said that without John Gillespie’s dedication and love for Sarasota, it would have taken “100 years for the average American city to acquire the same amount of public and private improvements as did Sarasota during that…boom period.”

John Hamilton Gillespie died in 1923 at the age of 70. On the eve of his death, Gillespie would have been able to see that his struggling Scottish colony had become an important tourist destination and prosperous city. His vision was now complete.


Street Marker at Golf Street and Links Avenue, Sarasota, Florida, October 1946. Courtesy of Florida Memory.


Source Credit: John Hamilton Gillespie: The Scot Who Saved Sarasota by Jeff LaHurd

Featured image courtesy of Wikimedia Commons