Highway 90 West: Old Spanish Trail Way Station

by Tim Gilmore, 2/19/2014, updated 10/1/2020

The face is flat. The orbital cavities are large and bulge at the outsides. The lower jaw is gone. Teeth are broken.

The bones of a domestic cat are scattered across the landing halfway up the vine-wrapped brick stairs to the balcony. Here lie several vertebrae, longer pieces of backbone and tail, and leg bones. And the skull.

Old Spanish Trail

photo by Wanda Glennon Canaday

Billy never knew what “business” his father conducted here, at least not when he was five years old. “I was goin’ in there with my daddy back in the ’50s,” he says. “It was a house of prostitutes upstairs, and on the bottom was a real nice bar, the Old Spanish Trail. It was prob’ly the elite place to go.”

The balcony stretches wide across the back of the Old Spanish Trail way station, hemmed in by the rusting arabesques of wrought-iron railings. From the balcony toward the distant trees are the nearby tattered palms, the piles of trash the weeds and forest humus reclaim, and the tin sheds and barns hidden in deciduous winter thickets.


“That was the place back in the ’50s,” Billy says, “where I went in there and my daddy said he had business to conduct, just sit in the car, he’d get me a Co’-Cola, some peanuts. A few times when hardly nobody was there, he brought me in, set me up at a barstool, said he had some business to take care of and he’d go upstairs. And boy, I thought that was a big deal to sit up there at the bar at that age. ’bout a half hour later, he’d come back down.”

The building clashes beautifully and decadently with itself. The porch railings that span the balcony could be straight from New Orleans. The yellow and red brickwork, quoining at the windows, and arches over windows and outside staircases give the building distinctly Old West / faux-Spanish overtones. Walls of outcropped coquina, the natural limestone found in rare deposits on Florida beaches, stand as testaments to the building’s origins.


It’s hard to decipher the truth about the building from the urban legends. I always try to discern the truth, but I don’t disrespect urban legend. Urban legend thrives even in this bizarre rural setting, because it’s folklore. Folklore concerns itself with the truth people try to make of life and their place in the absence of sure knowledge, and to disparage that would be to disparage my own heart.

In 2015, a group appealed to the Jacksonville Historic Preservation Commission for historic landmark status for the Old Spanish Trail Building, far out in the woods on West Beaver Street. The appellants claimed to know something of the history of the building, but provided no sources. The commission motioned to investigate the building’s history and consider possible landmark status.

way station 4

It’s true that Beaver Street, as this local highway is called, through Jacksonville and its western satellites, is part of U.S. Highway 90, this section of which was called the Old Spanish Trail, an echo of the earlier Camino Real, which ran from the Pacific Ocean at San Diego to the Atlantic at St. Augustine, Florida.

Oral history has it the building was constructed in 1835 as a stagecoach way station. A residential area called Thigpen, now Baldwin, developed itself to the west.

a back building behind the Old Spanish Trail, 2014

According to local unofficial history, 80 years after the way station and tavern was built, a “Spanish Colonial” architectural veneer was superimposed on the original structure. This would have been about 1915, shortly before Florida began its post-World War One land boom that featured houses and whole neighborhoods built in pseudo-Spanish “Mediterranean Revival Style” architecture. The location of this building, either new or remodeled, along the former Old Spanish Trail would have made its initial design, or re-design, make sense.

OST 19

In the Historical Preservation Commission meeting, appellants claimed, “The purpose of the highway was to encourage the notion that the trail followed the old Spanish roads, using the romance and historical paths to promote tourism.”

They claimed the way station was used both by Union and Confederate troops in supply lines during the Civil War, that it later became a tavern, then a brothel, a boarding house, and decades later, a roadside attraction that sold gasoline and such Florida tourist offerings as alligator heads, boiled peanuts, and jars of local honey.


Another urban legend has it that Al Capone hid here on his way south to Miami. Urban legends of every third old building in Florida name Al Capone, just as every bar old enough claims Hemingway drank there. The latter’s more probable. Billy doesn’t know the early history, he says, but knows what he remembers.

Billy, now in his 70s, grew up in Macclenny, the small town 30 miles west of Jacksonville, still lives there today. His father was a moonshiner, and Billy did some shining too in his 20s, but only as a side job. He’d rather I didn’t use his last name. “Back then,” he says, “Macclenny was known as the Moonshine Capital of the World. Then in 1975 or thereabouts, Baker County started growin’ marijuana instead. Today it’s pills and heroin and all that mess.”

photo by Wanda Glennon Canaday

About 20 years ago, Billy went into the Old Spanish Trail “when it was a salvage store. I was in my early 50s then. There was a lady workin’ there, said, uh, ‘We got stuff upstairs too.’ She said, ‘You know what that used to be, don’t’cha?’ I said, ‘It used to be a lot of women up there.’ She said, ‘So you know about it.’ I said, ‘I never did go up there, but I know a lot of men who did.”

Then he went up. He describes the large open living room upstairs, “then the great big kitchen, then all the little rooms, maybe six feet wide, eight feet long, about 10 of ’em. And that’s where things went on.”

Duval County Sheriff Rex Sweat, courtesy State Archives of Florida, floridamemory.com

On the weekends, Billy says, “the ladies up there hosted big poker games and all the bigshots out of Jacksonville come out there and it was high stakes gamblin’.” He’s always remembered Duval County Sheriff Rex Sweat’s involvement at the Old Spanish Trail.

When Sweat died, 91 years old, in 1986, headlines pronounced, “Ex-Sheriff Known for Fighting Organized Crime,” though he was also known for participating in it. Sweat was known for pulling the lever himself on men who died in the electric chair at the state prison down in Raiford. He left office after 25 years when, as attorney Ray Coleman once put it to me, he was “caught with desk drawers full of dirty money.” Dale Carson, the corrupt sheriff who replaced Sweat, said, “His most important contribution is that he never let organized crime get a foothold in Duval County.”

Duval County Sheriff Dale Carson, courtesy jaxsheriff.org

“Rex Sweat used to be out there a lot,” Billy says. “He was either a part owner or they give him a lot of the earnin’s, some kind of arrangement.” Sweat was sheriff from 1933 to 1957. Billy’s not sure how far back the Old Spanish Trail became one of his father’s “regular hangouts,” but he knows his father would leave him in the car, “always in the daytime,” with an ice cream or a Coke, starting about 1950. Nights and weekends were a different story. He says, “Sweat used to always be out there for the poker games.”

Since I first wrote this story, before Billy’s memories, in 2014, David and April Ussery Smith purchased the Old Spanish Trail and converted it to Halloween trails and a house of horrors. The previous owner, Joseph Menendez, who bought the place in 1959, grew up in New Orleans and added the balcony and railings. He turned the whorehouse into a grocery. He’d initially invited me onto the property “anytime,” but didn’t like my story. He wouldn’t say why, but did say that if I came back by, he’d have his shotgun ready.

April Ussery-Milward, Old Spanish Trail, photo by Mary Carver

Last year, the Old Spanish Trail’s Facebook page read, “After five years of screaming fun, we bid you farewell as we move on to our next chapter. The Old Spanish Trail will soon have a new life as a beautiful wedding venue. We are looking forward to seeing what the new owner’s vision will be. Thank you all for the amazing memories and support you have given us during our time here. We will definitely miss the sounds of screams and laughter but have made memories and friends to last a lifetime. Much love from our family to yours.”

farewell photo, courtesy April Ussery-Milward

Back in 2014, I ended my account this way:

Nearby, eight foot tall stands of brown dead broom sedge grow against a sunken house trailer, a basketball goal, and distantly spaced heavy iron bells. Dead vines encompass corroded lamp posts like crowns of thorns.

Shotgun shells litter the wintry dead-brambled ground in the woods alongside the highway. Vagabonds wander these woods up and down U.S 90, leaving behind scattered clothes, a wooden jewelry box, neglected books and magazines, a flashlight.

photo of Tim Gilmore at the Old Spanish Trail, by his sneaky sister, Wanda Glennon Canaday, 2014

Everywhere I travel across North Florida’s neglected spaces, I see evidence of North America’s vast and unaccounted-for transient populations.

Sweatshirts, old pairs of jeans and batteries decay into the forest floor. This place is clearly some kind of way station for people who’ve lost their way. Or people whose way is totally outside society’s.

My sister Wanda loves ruins like I do. She sees the beauty in the earth’s reclamation of the world and she makes it the subject of her photography.

depiction of Emerson’s “Transparent Eyeball” by Christopher Pearse Cranch, circa 1836-8

She reminds me of Ralph Waldo Emerson’s “transparent eyeball” in his 1836 poetic essay “Nature,” wherein he describes himself as “Standing on the bare ground,—my head bathed by the blithe air, and uplifted into infinite spaces,—all mean egotism vanishes. I become a transparent eye-ball; I am nothing; I see all; the currents of the Universal Being circulate through me; I am part or particle of God.”

People talk about “the real world.” My former-military students talk about coming back from the military to “the real world.” When I was a kid, adults talked about graduating high school to go out into “the real world.” But the real world is the earth from which arose the human world and to which everything human always returns.


So everything that’s happened along U.S. 90, and in this old structure with its multiple layers and veneers, makes this place and all the dead sedge and falling barns around it a way station between the world, which is always decadent, and the earth, from which everything arises.

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