Not much is recorded about the pre-Columbian history of Sugarloaf Key. There is evidence of a huge Native American Indian kitchen midden in the general area of today’s high school indicating pre-Columbian inhabitation. Habitation was probably not as permanent as we think of today, but more as temporary fishing or hunting site.

The area was homesteaded by William Sterling Baker and ownership passed on to Mr. B. C. Hopeman in the 1940s then to the Howe family. Later Bob and Viola Howe found an unidentified shipwreck in the process of dredging a channel. The area was first developed in the 1960s.

The serious Lower Keys history buff should refer to writings of John Viele, Historical Preservation Society member and local Cudjoe Key author of three Pineapple Press books (The Perilous Florida Straits, The Pioneers and The Wreckers) and countless newspaper articles, primarily the Island Navigator.

Sugarloaf Key was short changed in the name department on early maps. The eccentric British cartographer, DeBrahm named it Glen Kay in 1772 which is not bad for DeBrahm. DeBrahm visited many of the Florida Keys; however, when he needed a name he gave most of them English names. Windley Key was Wright Kay, Tea Table Key as Boys Key and Plantation Key was Bull Island. For the better established names he did better i.e., Key West was Hueso and Lower Matecumbe was La Vieja: however, he was thorough. He did name Keys that many of the others of 1700s period passed by without a name.

Sugarloaf Key is located about MM 20 between Cudjoe Key and Saddlebunch Keys. If driving south, you cross onto the island after crossing Bow Channel and if you turn left you will be on old state road 4-A going towards the once popular Pirates Cove Resort. If you are traveling south and turn right where you see the small airplane (June 2001) you will be entering the once community of Chase and Perky. The Perky Bat tower is about MM 17, then NNW (Gulfside) for a half mile off of highway US-1 then slightly off to your right.

To visit this area from the mainland before 1912 sea travel was used, after which in 1912 rail travel was also available. Vehicle travel became available in 1928 via State Road 4A and ferry boats. From Florida City one would drive over the wooden Card Sound Bridge onto Key Largo and on to lower Lower Matecumbe Key. There a ferry boat would transport you to No Name Key for the drive to Key West passing Sugarloaf Key on the road just mentioned. During the trip, one crossed the railroad twice. First on Upper Matecumbe Key at about MM 81 and remained on the right side going south until crossing the railroad again just after entering Sugarloaf Key. Most of the old highway bridges from this point on to Key West have been removed. In 1942, the Pirates Cove route was bypassed when the U.S. Navy shortened the travel distance by following the F.E.C. railroad route, the same route as today. The railroad ceased operation after the 1935 hurricane destroyed about 40 miles on track in the Upper Keys. In passing, the Card Sound route in the Upper Keys was also bypassed by following the railroad route via the so-called 18-mile stretch. About 14 miles were saved from Key West to Florida City in 1942. The Navy used federal funds, hence the name change to US-1.

The first recorded English settler actually living on Sugarloaf Key that the author found in the Key West library was Asa Gilbert in 1829. In the Territorial Court papers in the Key West Library are records that Asa Gilbert of Sugarloaf Key did not appear for a jury summons in 1829. He explained to the court that he did not have a boat and produced a witness to substantiate his testimony. As now, jury summons were serious and also a huge problem at that time. Fort Myers was a northwestern community of then Monroe County and traveling to Key West for jury duty was a lot to be expected.

Asa’s presence is verified by the 1830 census; however, for Monroe and Dade Counties the 1830 and 40 censuses only showed the head of the household, which Asa was head of a family of one, and the age groups. Asa was in the 50 to 60 year age group. He was not found in the 1840 census for Monroe County. I also checked Dade County just to make certain he had not moved. Remember in 1836 all the Keys north of Bahia Honda were in Dade County. These census reports are generally available on microfilm at your library, or can be purchased as the author did.

The 1850 census reveals three males residing on Sugarloaf Key. They were Jonathon Thompson, age 60, occupation planter; James Anderson, age 70, mariner and Robert Johnson, age 23, mariner. Jonathon Thompson was known as “Happy Jack” after whom there is a small Key, Happy Jack Key, nearby named.

According to a Putnam Monthly article, Happy Jack was one of a group of men who wandered throughout the Keys living wherever and however they were able. Others of the group were Paddy Whack, Jolly Whack, Red Jim, Lame Bill, and Old Gilbert. Quite possibility, Old Gilbert was the aforementioned Asa Gilbert.

The Putman author went on “. . . However different their names and varying dispositions, they all united in a common love. The fragrant goddess of whiskey absorbed the affections of their guileless hearts. . . . Jack was always disinclined to the world, and Key West probably did not elevate his opinion of human nature. So he settled himself permanently on the key [Sugarloaf Key] we have just described and bent his energies to trapping deer and raising fruit. He is still alive [1856], and likely to live. His solitude is not so uncompromising as Robinson Crusoe’s, for the crowds of spongers and fishermen that swarm around all the keys give him sufficient company, indeed more than he deserves.”

Happy Jack died less than two years after the article of wounds after tripping a anti-deer gun while he was out walking. Local deer had been a problem to farming on the Lower Keys and trip wire guns had been rigged along the paths of the deer. Happy Jack’s farm was on Bow Channel and north of the SR-4A and the railroad crossings.

The 1860 census revealed only one person, a Daniel Dennis, age 55. occupation sail maker from North Carolina. Sail making was probably his skill; however, farming and/or fishing would be more probably. Of course, Happy Jack was no longer with us.

The 1870 census revealed a population explosion. A total of 37 people divided as follows: 17 children, 8 seamen, 6 keeping house, 2 wood cutters, 2 laborers, 1 farmer and 1 boatman. Probably the demand for food in Key West during the Civil War generated this increased population. Key West was a major Gulf Blockading Port for the Union and whose relatively rapid population increase considering its physical size would continue until 1890. Early permanent island settlers in unincorporated Monroe County were difficult to find. This is demonstrated by the Johnson family who represented one third of the 1870 population, but 10 years earlier were farming on Cudjoe Key.

Another recorded farmer of Sugarloaf Key was Dr. J. Vining Harris (MD), Confederate veteran, permanent resident of Key West, later Superintendent of the Monroe County School Board and namesake of Harris School in Key West. Harris was also the builder of the Southermost House on Duval Street at Key West.

Dr. Harris’s farming efforts were well known in Key West in the late 1890s; however, there is no documentation of him ever shipping a product. In 1897, Dr. Harris added a new element to his farm – sponge cultivation. According to John Viele’s The Florida Keys, A History of the Pioneers, about 1901, he turned over the use of his property, and the house he had built, to Dr. F. H. Moore, head of the U.S. Department of Fisheries to continue the experiment.” As far as we know good reports were the only export.

In 1905, Henry Flagler announced that he would construct an extension of his Florida East Coast (F.E.C.) Railway from Homestead, Florida to Key West. To do this he established work camps throughout the Keys. From an unknown newspaper articles, but hand dated 1906, “At present there are 12 camps. No. 80 is on Big Pine Key. No. 81 on Summerland Key and No. 82 at Key West. About 100 negroes are employed in grubbing and butting out the undergrowth preparatory to constructing the road bed. These men have separate camps and buy their supplies at from the commissary: many have their families with them to do the cooking.”

It appears that that the railroad was the next to user of Sugarloaf Key. The records are not complete; however, it appears that the railroad only leased the Harris house. The author finds little written about the railroad’s use of Sugarloaf in the newspapers. In fact, Dr. Harris is found treating the sick and injured at Knight’s Key and Key West more than any place else.

One of the next permanent Sugarloaf Key residents were Charles and George Chase. Charles Chase with wife, Hettie, visited Key West in the summer of 1899 with a play that he had written, then visited again in 1906. On a later visit to Key West, he met Dr. Moore and became intrigued with sponge cultivation. In 1910, he and brother George, plus a group of English investors, established the Florida Keys Sponge and Fruit (FKSF) Company.