By Joy Wallace Dickinson and Rick Kilby from the Spring 2025 Edition of Reflections Magazine
“With the coming of the railroad Orlando’s days as a pioneer town were numbered,” historian Eve Bacon wrote about the event that made Orlando accessible from Sanford and in essence all points north, by train and steamboat. Before the first train arrived on Oct. 2, 1880, a journey to Orlando, Florida’s largest inland city, required rugged travel over crude roads on horseback, by stagecoach, or on foot. When future Orlando mayor Mahlon Gore first arrived in the spring of 1880, it took him two days to walk from Sanford. These were not conditions to encourage prospective settlers or recreational visitors to pay a call.
But, according to Bacon, the railroad led to a boom that inspired the construction of a three-story brick hotel, the Charleston House, at Orange Avenue and Pine Street, at a time when some complained bricks were so scarce that it was hard to construct a chimney. The Charleston House became the site of future balls, banquets, and political gatherings, leading a westward shift in the city’s commercial center, away from Main Street and the county courthouse and closer to Orange Avenue.
Fueled by the railroad, Orlando experienced its first population surge, mushrooming from about 200 people in 1880 to 4,000 by 1886, despite a destructive fire in 1884. Boosters dubbed it the Phenomenal City, built on the peel of an orange, a vision dimmed when the back-to-back freezes of late 1894 and early 1895 devastated citrus crops.
While early northern tourists wintered in nearby Winter Park and Altamonte Springs at luxury resort hotels located on lakes, Orlando would offer lakeside accommodations for northern visitors of a different type. Seeking relief from icy winters, they sought out Orlando for health reasons after physician R.L. Harris opened a sanitarium between lakes Estelle and Winyah near the turn of the century.
The Seventh-day Adventist Church, which popularized health-care regimens such as hydrotherapy, physical exercise, and healthy eating at the famous Battle Creek Sanitarium, purchased the facility from Harris in 1908. Decades later, the Adventists’ Florida Sanitarium would grow into today’s Advent Health.
Orlando’s lakes would also become a draw for visitors who traveled to Florida for hunting and fishing. Orange County’s prolific promoter Will Wallace Harney bragged, “I have known of twenty fish, none less than a foot long, taken in forty minutes, which allowing for time for removing the hook and baiting it as fast as one can fish them up.”
Boating also became popular. Members of the short-lived English Colony organized sailing regattas at their club on Lake Conway. Guests at the nearby Macy Hotel used the Crittenden Dock on the big lake for boating and fishing, and Pleasure Beach became a popular recreation spot with a long dock and bathing pavilion for dancing, skating, and gambling. Further north on Lake Ivanhoe, Russell’s Point, later advertised as Joyland, offered boating, fishing, swimming, and dancing and was likely the location of Orlando’s first waterslide.
All Roads Lead to Orlando
“Orlando proudly claims the distinction of having taken the initiative in the organized Good Roads agitation,” declared a 1913 promotion for the “beautiful city” that invited visitors to “bring your auto and enjoy our good roads.”
Begun in the late 19th century as a coalition of farming interests and bicycle enthusiasts, the Good Roads Movement was a nationwide crusade that grew as automobile travel became popular in the early 20th century. It culminated in the creation of marked interstate road systems such as the Lincoln and Dixie highways. Organized by Miami Beach promoter Carl Fisher in late 1914, the Dixie Highway system had two initial north-south alignments, the western-most route of which bisected downtown Orlando.
Just a few years after Henry Ford’s Model T made the dream of automobile ownership accessible to many Americans, more people could reach Orlando than ever before. In the early 1920s especially, they drove down in a wave fueled by the Florida land boom. “It looked like the world on wheels was coming to Florida,” wrote Orlando developer Carl Dann.
These auto travelers did not stay in posh resorts or dine in luxury. They often depended on their own resourcefulness and favored budget travel. Dubbed “Tin Can Tourists” either for their mode of transportation (Model T Fords were nicknamed Tin Lizzies) or their penchant for bringing along their own canned food, these new travelers soon organized and began staying in campgrounds and tourist courts around the state. Hoteliers and restaurant owners weren’t impressed, and some Floridians were inspired to quip that many auto travelers arrived from the North with one shirt and one $20 bill – and, during their stay, changed neither.
Orlando embraced the Tin Canners somewhat grudgingly. According to a 1921 Orlando Sentinel article, the Chamber of Commerce advised that the camping tourist “should not be treated in a hostile manner” but should be “welcomed as any other visitor to the Peninsular State, able to pay his way and forced to do so.” Entrepreneurs such as Harry Hand, brother of funeral-home owner Carey Hand, embraced the motoring hordes by opening tourist camps, in Hand’s case between South Street and Central Boulevard – the site of today’s Carl Langford Park.
In contrast to the tolerated campers, some visitors achieved celebrity status in Orlando, where their arrivals were reported with fanfare. In 1929, the Orlando Evening Star referred to New Jersey financier John Jay Phelps, a dedicated snowbird, as “a very wealthy and socially prominent gentleman” who “influences a considerable number of tourists to come here each season.” Phelps and his wife wintered in Orlando from the 1920s until the year he died, 1948, when the Sentinel noted that his annual fall appearance had long signaled the start of the year’s social season.
Towering Hotels and Tourist Courts
The early 1920s also brought a boom in more traditional accommodations as Orlando saw its first “skyscrapers” in downtown. In 1922, an eight-story tower was added to the original 1885 portion of the San Juan Hotel, which owner Harry L. Beeman of chewing gum fame had enlarged to four floors in 1887. The Angebilt Hotel, named after developer J.F. Ange, offered 240 guest rooms in a million-dollar structure designed by local architect Murry S. King. A more modest, three-story building on Lake Eola, the Bonnie Villa Hotel, opened in 1924, showing the viability of accommodations outside the city center. It soon became a medical clinic but would become a hotel several more times over the years, most recently as the Eo Inn.
Other accommodations were less grand, such as Hovey’s Court, a collection of nine two-story Arts and Crafts-style guest cottages, built between 1913 and 1919 at 545 Delaney Ave. Black travelers had few choices for accommodations during the Jim Crow era until Orlando physician William Monroe Wells opened the Wells Bilt Hotel in 1929 (now the Wells’Built Museum). Wells also constructed the nearby South Street Casino, an entertainment venue that over decades hosted performances by artists including Louis Armstrong, Ray Charles, and Ella Fitzgerald.
While automobile traffic had changed travel patterns to Orlando, railroad travel remained significant. In 1926 the Atlantic Coastline Railway built the expansive California Mission-style station on Sligh Boulevard that continues to serve rail passengers today.
Another important addition to Orlando’s tourist landscape in the 1920s was the opening of the Dubsdread Golf Course in 1924 by developer Carl Dann. He expanded the course in 1926 to include 18 holes, and the Florida State Golfers Association’s 13th Annual Amateur Golf Championship was played there in 1927, about the time the Florida land boom began to collapse. The Sunshine State experienced the financial crash that would hit Wall Street in 1929 earlier than much of the country, after the 1926 Miami hurricane and the 1928 Okeechobee hurricane caused damage that bankrupted investors. Growth in Florida came crashing down as the nation lapsed into the Great Depression at the end of the decade.
Depression and Wartime
In an effort to stimulate the economy during the Great Depression, the federal government created a guidebook to Florida as part of the of the Federal Writers Project – employing now-legendary writers such as Zora Neale Hurston and Stetson Kennedy to document the state’s culture and create driving tours for visitors.
The Orlando section of the book, published in 1939, lists recreational facilities for baseball, swimming, tennis, golf, shuffleboard, lawn bowling, and roque, which is similar to croquet. The venue for the last three sports was Sunshine Park, which included large recreational grounds, the Municipal Auditorium, and Exposition Park, home of the Central Florida Exposition. Outdoor recreation and sports were a constant point of emphasis throughout the history of Orlando tourism promotion, from Major League Baseball spring training at Tinker Field to bass fishing in the nearby lakes.
Other points of interest in the 1939 guidebook include Lake Eola Park and the Orlando Zoo at Livingston Avenue and Garland Street. The section on Lake Eola offers a brief history of Orlando’s swans, including the fearsome “Mr. Bill,” known today as Billy the Swan, who died in the early 1930s and was preserved by taxidermy and displayed at the city’s Chamber of Commerce when the guidebook was published. (Billy is now in the Orange County Regional History Center’s collections.)
In 1940, the United States Army assumed control of the Orlando Municipal Airport, which had opened in 1928, and transformed it into Orlando Army Air Base. Another facility, Pinecastle Army Airfield, would open farther south in 1942 on that land that ultimately would become the Orlando International Airport. The infrastructure created during the war made the region more accessible for future visitors. More importantly, thousands of GIs who lived and trained in Florida would return after the war to visit or become new residents, and as historian Tracy Revels notes, the “image of Florida as a vacation destination for families began to dominate the public perception of the Sunshine State.”
A tourism survivor from those postwar years began in 1949, when Owen Godwin Sr. opened the Florida Wildlife Institute, now known as Gatorland, on U.S. Highway 441 near the Osceola County line. Created on land used for borrow pits dug to provide dirt for the roadbed, the 110-acre attraction celebrated its 75th anniversary in 2024 and is still family owned.
During the postwar years, the portion of U.S. 441 in Orlando was dubbed the Orange Blossom Trail, playing off the popularity of Florida’s most popular agricultural product. A.C. Slaughter, secretary-manager of the Greater Orlando Chamber of Commerce, was one of the founders and long-time president of the Orange Blossom Trail Association. A brochure for Orlando’s Fort Gatlin Hotel devotes an entire spread to the Trail and urges visitors to follow the highway of rolling hills “past thousands of green and golden orange groves.”
Citrus, perhaps the state’s most important crop, was itself an attraction with countless scenes of orange groves appearing on postcards sent back home. Roadside citrus stands took advantage of the highway hordes visiting each winter.
In addition to attractions such as Gatorland, other buildings sprouted up along Central Florida’s roads during the postwar period – this was the age of the motel. Tourist corridors followed highways 17 and 92, as well as U. S. 441, and all three roads followed the same route through much of Orlando.
The Mills Avenue stretch of 17-92 boasted the Flamingo Court Motel, Orlando Motor Lodge, Crescent Court Motel, and Motel South. The roadway then followed Colonial Drive to the Orange Blossom Trail with more motels, including the Davis Park Motel, the Gifford Arms Motel and Motor Lodge, and the Royal Motel, all of which still stand today but have been renamed. Today, however, Orlando’s best-known motel from the past may be the Wigwam Village on the South Orange Blossom Trail.
Built in 1947 and demolished in 1973, Orlando’s Wigwam Village at 700 S. Orange Blossom Trail was among seven similar “tourist courts” across the country. They all followed a design Frank A. Redford patented in 1937 after he opened the first one in Horse Cave, Kentucky. Orlando’s was the largest, with 27 concrete-cone units arranged in a horseshoe and four more facing the highway. Of the seven Wigwam Villages, the three that survive – in San Bernardino, California, Cave City, Kentucky, and on U.S. Route 66 in Holbrook, Arizona – are all on the National Register of Historic Places.
In their postwar heyday, such motels represented the freedom of the open road for many tourists – a freedom not extended to African American travelers during the era of segregation. To find the few accommodations available to them, Black visitors turned to a publication titled The Negro Motorist Green Book. The 1956 edition listed only two places to stay in Orlando: the Wells Bilt Hotel and the Sun-Glo Motel, on the Orange Blossom Trail, which opened in 1955 and advertised itself as “A Highway Hotel Catering to the Elite Colored Clientele.”
From Agriculture to Tourist Culture
A series of devastating freezes in the 20th century helped pave the way for today’s tourism-based economy in Central Florida. When Walt Disney officially announced his plans for Disney World at downtown Orlando’s Cherry Plaza Hotel in 1965, Orlando had been rolling out the red carpet for winter visitors for more than 80 years. Warm temperatures and glorious sunshine were a factor in Disney’s decision to locate his new attraction in the area, but it was the once again convenient transportation that sealed the deal. Flying over the location where the Florida Turnpike intersected Interstate 4, Disney imagined throngs of motorists heading south on speedy highways. Those same modern roads, however, diverted traffic from colorful “blue highways” such as U.S. 441 and 17-92, and many of the mom-and-pop motels and restaurants that defined the roadside experience at midcentury later fell by the wayside.
With Disney came other attractions hoping to get their slice of the tourist pie in the 1970s, including Church Street Station in downtown Orlando. Bob Snow, the nighttime attraction’s creator, chose the Church Street location because of its proximity to the then-derelict historic train depot, ironically the same place where visitors once took their first steps in the City Beautiful.