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Early Settlers in Flamingo

One of the first to come to Flamingo, and who was here when the settlement was named, was Duncan C. Brady, of a New England whaling family. He had drifted to Florida, and to Madeira Hammock, east of Flamingo, where he built a palmetto shack. In his sloop Linda C. he hauled charcoal to Key West for other settlers, for there already was a little settlement at Madeira Bay.


After moving to Northwest Cape and then to Middle Cape, where he found Jim Demery with his wife and six children already living, Brady bought a claim at Flamingo. This area was surveyed in 1903. Only nine settlers were recorded then. Besides Uncle Steve L. Roberts and his eldest son, Eugene, there were C. Dalrymple, N. Nelson, D. J. Bronson, M. Mason, H. R. Fiers, R. D. Vaning and R. M. Weaver. Soon after this, Edwin R. and Lydia Bradley, with their sons Louis and Guy, bought a quarter mile claim on the waterfront. Edwin Bradley had been one of the "barefoot mailmen" who walked the. beach between Palm Beach and Miami. Later he was superintendent of schools for Dade County, then as land agent for the F.E.C. Railway and the Model Land Company, he moved to Flamingo, where he became postmaster.




When Dr. Henry Perrine was given a grant of land in South Florida in 1838 his selection was “along the south coast of the peninsula eastward of Cape sable and northward of the sandy isles”, which he described as “the she1tered seashore of an ever verdant prairie, in a region of ever-blooming flowers, in an ever-frostless tropical Florida. He envisions a colony or free white settlers in the area and part of his dream included a canal from the interior to bring water power for their needs. His untimely death at the hands or Onekika and his Spanish Indians in 1840 put an end to his dreams and his plan died with him.


Cape Sable was also brought to the attention of the U.S.  government when Surgeon General Thomas Lawson led an expedition in February 1838 in search of Spanish  Indians and decided to build Fort Poinsett on the most southern point of the Cape. He proposed that the whole Lower Peninsula be occupied by settlers to hold the Indians in check. During the third Seminole War in 1856 Fort Poinsett was reactivated and. Fort Cross was established at Middle Cape. There is no record of any remains of this fort but outlines of Fort Poinsett remained until the 1935 hurricane. No doubt the scarcity of food in Key West during the Civil War prompted the farming of Cape Sable prairie at that time and from then on there was limited occupation and farming in the area.


The first to get the inhabitants together in any degree of permanency was Duncan C. Brady from Nova Scotia who arrived with his family on his schooner the Linda C. in 1893. He spearheaded the drive for a post office.

The settlers met and chose the name or Flamingo for their area as it was the most distinctive of the many birds wh1ch abounded at that time. Mr. Brady was the first postmaster followed by Judge Howard Cobb Lowe,  Edwin R. Bradley, Robert Douthit and Eugene Roberts. The post office survived unti1 1914.


Duncan Brady lived at various places on the Cape but was unhappy with all of them as he felt the open beach offered no protection from hurricanes.  He moved his family of five girr1s and two boys to Chokoloskeeso they could attend school. His oldest  daughter Maude married James Robert Simmons and returned to South Dade in 1910. Their son Glenn took to the woods when he was fourteen years old as the family was very poor and supported himself by hunting alligators and otters. Later he became a guide for such eminent writers as Dr. Charlton W. Tebeau and Dr. Frank C. Craighead.


The land at Flamingo and Cape Sable had not been surveyed for homesteading but under a preemption law of 1841 settlers could file a claim on land and pay $l.25 per acre after a government survey was made. James A. Waddell of Key West acquired 120 acres comprising much of the beach front of the Cape and planted it with coconut palms. A number of claims were filed in 1884 and then sold to Waddell. At Flamingo the land was claimed in 80 acre strips with about one quarter mile of beach front each.


In 1903 when there was talk of running the Florida East Coast Railroad through there the land was surveyed and the claims taken up by the occupants, Uncle Steve Roberts and his wife Dora Jane with their sons Eugene, Ward, Jim, Melch and Loren arrived at Flam1ngo in 1901 and occupied the land farthest east on the prairie where the park headquarters now stands.

In 1908 he sold the north-west ten acres to Louis Loudon. Eugene Roberts, oldest son of Steve held the next claim to the west. He marr1ed Addie Tanner of Orlando.


The Irwin family arrived in 1898 with their sons Coleman, Kay, Frank and Virgil and daughter Carrie. A son by Mrs. Irwin's first marriage, Ray Gooding, was also with them. Mr. Irwin was a brick maker and layer and was looking for clay soil. He died in 1901 and Mrs. Irwin managed to keep things going with the help of the boys, She filed for a homestead on Joe Kemp Key in 1916. Carrie married. John Douthit in 1905 and Coleman later bought some beach front from the Douthit claim and built a dock and house over the water. Frank Irwin married Pauline Watson and homesteaded Frank Key in 1918.


John Douthit’s land was to the west of J. A. Worley who owned a narrow strip next to Eugene Roberts. West of Johnny Douthit was a claim owned by a man named Merriman. Nothing is known about him. The Douthit children were Sennie, Mary (Madie), John and Joe. The Douthits left Flamingo in 1920 and bought the Alex Conrad home in Peters.


Steve Roberts' younger son Loren held the next 80, acres. He married Effie Tanner; sister of Addie, Loren was eventually the most successful of the Roberts brothers and owned a large fi3h house, boats and trucks at Flamingo and a house in Florida City where he moved his family when his children were of school age.


West of Loren was the claim of Robert Douthit, brother of John, who arrived in 1900 from Lemon City and grew sugar cane and sweet potatoes He purchased the cla1m of Jack Matthews 80 had 160 acres. Bob had married Edith Sayers in 1898. Their children were Robert Jr, Tip, Cecil, (Buck), Thelma, Gladys and Frank (Pete). Douthit owned the largest boat in the area, the Eva Pearl, which carried produce to Key West for the community and brought back supplies. Bob Douth first moved his family to Peters 1n 1910 after a hurricane salted the prairie land He worked as a manager tor his brother-1n-law Tom Peters. He kept his land at Flam1ngo and often hunted and fished there. Mr. A. P. Curry and his niece Mrs. Barcus had a small store at Flamingo near the Roberts. He d1d not sell groceries but carried tobacco and sundries. Mrs. Barcus later went to Princeton where she taught school and homesteaded.


Edwin R. and Lydia Bradley came to Flamingo as land agent for the Model Land Company 1n 1902. He had formerly been a barefoot mailman. His sons Louis and Guy and he each acquired a quarter mile of water front. Guy Bradley was appointed game warden for the National Audubon society and was killed protecting a rookery from plume hunters. He was buried at East cape and a memorial erected which is now about 100 feet out in the bay.


“Judge” Howell Cobb Lowe, the local Justice of the Peace, lived out near East Cape.  George Davis 1ived at north-west cape at the coconut grove and raised white leghorn chickens and fed them on coconuts.  In 1903 the Raulerson brothers established a large cattle ranch on the East Cape prairie. It did not survive largely, it is believed, because the prairie grass did not contain the proper nourishment for the cattle rather than the swarms of mosquitos and deer flies which were often blamed.


During the heyday of the colony in the late l890's and early 1900’s, thousands of dollars’ worth of plumes were collected and sold by the hunters, many to Rodney Burdine. The main occupat1ons of the settlers was fishing, hunting, guiding hunters, making "coal", growing sugar cane and making syrup. At first only a horse powered mill was used to grind the cane and make syrup but 1n 1910 Louis Loudon and Loren Roberts bought a steam powered mill and set it up in Flamingo. During the years the work on the Key West Extension was in progress they found a ready market for their product in feeding the workers.  


Making moonshine whiskey used up most of the available supply and furnished a large part of the Cape economy. Fishing was the most common business. In 1908 the Crossland Fish Company of Miami sent a lay boat to Flamingo which brought ice and supplies to the settlers and bought their fish daily. Black mullet caught by nets from boats was the big summer commercial catch. There was also considerable farming and hunting around Coot Bay.


Allen Chandler planted a lime grove there in the teens and sent his son Luther to look after it when he lost interest in school. Luther had a boat named the "Bellyache” which he later traded for a larger one named the “Estelle” which was the biggest coat on the Cape He carried most of the settler's produce and coal to Key West. Luther lived with Loren Roberts.


Except for the Waddell grove and the homesteads at Flamingo, all the land at the tip of Florida went to the Florida East Coast Railway in 1912 when they completed the Key West Extension. A road of sorts was built from Florida City to Royal Palm Hammock in 1915. Digging the Homestead Canal provided the fill, but work stopped at the Monroe County line until 1922 when the real estate boom gave rise to plans for a new city with hotels and tourist attractions.


The Cape Sable Development Company was capitalized at a million dollars but the boom collapsed before theplans got underway. Of the 260,000 acres given to Flagler for the building of the railroad 210.000 were in the Cape Sable area. The Model Land Company spent $300,000 building the Ingraham Highway and digging the Canal. They sold their holdings to the government for the park for $295,000.


Excerpts from “Man in the Everglades” by Charlton Tebeau and from “Gladesmen” by Glen Simmons

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