Visit to Loop Road and the ghost town of Pinecrest

Some photos and historical notes from a remote drive to nowhere in Big Cypress National Preserve - formerly the Big Cypress Swamp. Loop Road and the vanished small town of Pinecrest played an important role in the history of this corner of Florida during the first half of the 20h century. 

The cypress swamp by Loop Road in South Florida - License our images here.

Of course, Loop Road is a loop. It begins at the Tamiami Trail and returns to the Tamiami Trail - at another point 24 miles later. Once inside, there is no escape. Neither gas, food, water, and in some parts, phone reception. This area is as remote as you can get in modern Florida without leaving the comfort of your car. 

Our truck in Loop Road. The route is mostly straight. The eastern side is paved, the west is all dirt.        

The eastern entrance is 40 miles west from downtown Miami, by the Miccosukee Indian Tribe. Loop Road follows the old Tamiami Trail, the original, the one the Florida government is removing to restore the waterflow of the Everglades - check this photo. Here there are homes of the Miccosukee Indians - modern homes, no tepees anymore. The houses are built on high ground and alligators were sun basking near their cars. Children toys scattered over the unfenced patios. Their children still know how to deal with wildlife, ours have forgotten. 

Loop Road runs for a couple of miles on lands of the Indian Reservation. Be respectful there.

Old picture of the east side of the Big Cypress swamp by Loop Road - Source: Florida Archives. 

Then comes the preserve. Big Cypress National Preserve was the first one created in the US. It happened in 1974 and came with discussions and disagreements because part of the lands was private property. An article from 1917 of Forest and Stream paints this place as, 

…an imposing watery, swampy area known as "Big Cypress"…

Soon, we arrived to what is left of the town of Pinecrest. 

Three of our photos by Pinecrest and Jim Dill Road. There is not much left there.

If you like ghost towns, you got another one here. Pinecrest's "downtown" was at the junction of Loop Road and Jim Dill Road. 

Jim Dill is a dead-end route. Satellite images show old streets covered by vegetation and probably partially flooded. Who was Jim Dill? A resident of Miami and a veteran of three wars that moved to the swamp. Check a photo of Jim Dill from 1943.  

The pumps of Pinecrest Service Station survive at the intersection. A sign says that it opened in 1920.

The rusty Pinecrest gas station at Loop Road. When Pinecrest died down, the station ran out of clients - ghost towns are bad for business. The Pinecrest station is on a private property. This photo was taken from the street.   

James Franklin Jaudon, a retired Army captain and tax assessor of the city of Miami in 1915, was the "father" of the Tamiami Trail, Loop Road, and the town of Pinecrest. 

The construction of the Tamimi Trail in the 1920s - Source: Florida Archives.

Jaudon founded Chevelier Corporation in 1917 and ordered surveys of the Ten Thousand Islands to build a community at Chevelier Bay, 12 miles south of Chokoloskee - we've a photo of Smallwood’s Store in Chokoloskee at the end of this post. 

The name of the company probably comes from James Chevelier or Chevalier, a French bird hunter that got feathers in the Ten Thousand Islands to sale in Europe - plume hunting. 

Some sources say that Chevelier was a friend of the American outlaw Edgar Watson, the man killed in 1910 in the shootout at Ted Smallwood’s store - many photos in this page. 

Jaudon also bought land along the planned route of the Tamiami Trail to profit from the new road construction. The prospectus of easy money brought investors and speculators. An article from 1917 explains: 

Captain J. F. Jaudon, working with the Miami Commissioners, and a group of financiers who never for a moment doubted the ultimate result of the deal, bought in the Tamiami Trail Lands as a safe and sure investment.

Jaudon hired the surveyor John King to chart the area of Pinecrest and the route of the future Tamiami Trail. King worked for him before in the survey of Chevelier Bay. In this old map the Pinecrest area is marked as "the property".

Old map marking the area of the Pinecrest land tracts - Source: Florida Archives.

The road built to Pinecrest was known as Chevelier, but the locals called it "Chevrolet" - this was the eastern side of Loop Road. The Florida land boom of the 1920s supported the sale of tracts along the new road. Jaudon dreamed big thinking of building the "next Miami" in Pinecrest. There are advertisements from these times in the Archives of the State of Florida. These are excerpts. 

Pinecrest will have no competition from other towns, for there are no other such high pine lands on the Tamiami Trail for 46 miles east to Miami.

If you want a little real happiness, pick a few business lots near the center of Pinecrest at less than $1,000 each, and in a year or two when other fellow offers you from $5,000 to $10,000 for your bargain,

But Jaudon's business hit a bump: the construction of the Tamiami Trail ran out of money. 

Photo of the construction of the Tamiami Trail in the 1920s - Source: Florida Archives. 

Barron Collier came to the rescue but demanded to reroute the Tamiami Trail through Collier County. This detour created the big curve of the 40-mile Bend by the Indian Reservation and the Tamiami Trail bypassed Pinecrest. The prospectus of making money from the lands around the town ended. 

The Tamiami Trail was completed in 1928. A convoy of 500 cars travelled from Tampa to Miami to celebrate the event. 

Cars in the Tamiami Trail in the 1920s - Source: Florida Archives. 

Took 13 years to complete the Trail at a cost of $8 million - $100 million in today’s dollars. 

There was an arch marking the boundaries of Dade and Collier counties that was demolished to widen the road. 

The arch of the Tamiami Trail was removed in 1958 - Source: Florida Archives. 

The town of Pinecrest was left with an unfinished Chevelier Road that was supposed to be the Tamiami Trail. Later, the Florida government completed this road, and it became our Loop Road. The addition was the dirt part of the road that ends near Ochopee - "Big field" in Seminole. 

Chevelier Corporation went bankrupt. Captain Jaudon sold his lands to the Federal Government and moved to Ochopee working as the first postmaster of the area.

Ochopee post office at the Tamiami Trail in the 1940s - Source: Florida Archives. Note how many businesses there were around. Now all are gone. 

This is the smallest post office in the United States today. It seats alone facing the Tamiami Trail. 

A lonely shack today as you can see in out photo, but still a working post office serving Ochopee and the surrounding area.          

The government bought most of the land around the town of Pinecrest and created Big Cypress National Preserve. Some folks refused to sell and a few still live in the remote area.

There are interesting tales around Loop Road and Pinecrest. One says that Al Capone owned a gambling lodge here. Another, that this is the resting place of Jimmy Hoffa. "Al’s lodge" burned by the end of the 1920s and Jimmy Hoffa’s body was never found. What we know is that this remote wilderness was a moonshine paradise during the prohibition. There are photos of police raids.

Pinecrest became a rough place. One of the old residents - Ben Wolfe - said in an interview that a cousin of Capone owned the lodge that burned in 1927. Mr. Wolfe also had respect for the big alligators in this area.

I wouldn’t dare step out of my place at night if I didn’t have a gun in one hand and a flashlight in the other. And I’d still be scared because there’s some twelve- or fourteen-footers around. 

This map from 1939 shows the city of Pinecrest halfway between Miami and Naples.

Old map of the Florida Department of Transportation showing Pinecrest - Source: Florida Archives. Small Indian villages are also marked on the Tamiami Trail.         

Close to Pinecrest appears an unknown place called Trail City. Another mystery. We stopped by this spot and saw nothing. The swamp took all over.

The Gator Hook was the social center of Pinecrest. A sign ove the door welcomed everybody.

No guns or knives inside.

There was alcohol and bluegrass music up to one in the morning. Locals, Indians, and a few folks from Miami came here for a dose of wild fun. Some accounts talk of shooting contests using dynamite charges as target. The owner of The Gator Hook was Jack Knight, a former police chief of Sweetwater - the old name in the times of the Florida land boom was "Sweetwater Groves".

The fiddle player Ervin T. Rouse was one of the musicians working in The Gator Hook. He lived in Pinecrest and was the author of "Orange Blossom Special".

Well, I’m going down to Florida

And get some sand in my shoes

Or maybe Californy

And get some sand in my shoes

I’ll ride that Orange Blossom Special

And lose these New York blues.

Johnny Cash made the song famous - listen here. I also like this harmonica interpretation by Buddy Greene.

The Gator Hook closed in 1977. 

Pinecrest also had the Sullivan Barbecue. The owner was Don Sullivan, a man from the city of Homestead. The two-storied building of the business it's said was decorated with antiques. 

Today, you can meet Lucky Cole by the former Pinecrest area. He is a skilled photographer that keeps fascinating tales of the good old times. We met Lucky and Maureen in 2007. Great folks that still live in Loop Road. 

Entrance to the campground of Mitchell's Landing on Loop Road near the site of the former town of Pinecrest.         

Paved Loop Road ends by the Environmental Education Center of the preserve.

Small house inside the preserve education center in Loop Road. 

Across the center, there is the trailhead of Tree Snail Hammock. This short trail goes through a hardwood hammock. The name is about species of tree snail native to this area. A warning sign at the trailhead reminds that this is Florida panther habitat. Keep the children close. 

During the dry season the canal along Loop Road is booming with alligators. 

Alligators sun basking on the sides of Loop Road in Big Cypress National Preserve. 

Miles later, our favorite spot of Loop Road: the narrow bridge over the Sweetwater Strand. 

The Sweetwater Strand at Loop Road - view to the south from the narrow bridge. 

Strands and cypress domes are part of the swamp. The difference is that strands are linear, and domes are circular. In both cypresses grow on the shallow water of the banks. The water level changes a lot between the dry and the rainy season.   

The bridge on Loop Road, the Sweetwater Strand during the rainy season and in the dry season.

Bromeliads, orchids, and Spanish moss adorn the trees around the strand. Birds are plenty and make the place sound like a real "Jurassic Park" - gators play the role of dinosaurs.

The Gator Hook trailhead. Here you find the first toilet in Loop Road. 

The Gator Hook trail was a logging tram road. It goes for five miles, but parts get flooded. Lucky if you reach a mile and don't lose the trail - winter offers a better hike. 

Two miles from The Gator Hook trailhead, Loop Road joins again the Tamiami Trail. The Monroe Station used to be right at this intersection, but a photographer burnt the building. We were lucky to get a photo before it was gone - in this page you can read what happened and see a photo of the gas station during its best times. 

The dilapidated Monroe Station at the Tamiami Trail by Loop Road. 

This was one of six gas stations built in the 1920s. There were also stations for the Southwest Florida Mounted Police to keep order and aid motorists in the Trail - these were paid by Barron Collier. 

In our time, Loop Road is changing again. We noticed that its remoteness is becoming something of the past.

The following links take to other posts about South Florida that you may find interesting.

• Everglades National Park: A photo journey
• Chekika: Forgotten spot of Everglades National Park
• Ruins of Aerojet: The abandoned rocket plant of South Florida

Sources for this post:

Lost in the Everglades, Livingston Larned, Forest and Stream, December 1917 (Page 586)
Close Encounters of the Swamp Kind, Kirk Nielsen, Miami New Times, May 1999.
The Gator Hook bar was as wild as the Everglades outside, Tampa Bay Times., 2012.
A Tangential History of the Tamiami Trail, By Ross Hancock.
Researching the History of the Everglades, Exploring Florida History.
Everglades Exploration Network
Florida Memory: State Library and Archives of Florida.
Everglades Biographies: James Franklin Jaudon, Reclaiming the Everglades, Florida International University.