IN 1849 William A. Whitehead donated a map of Key West, Florida, to the New Jersey Historical Society in Newark. A memento of his first sojourn on the island and the result of his surveying it twenty years earlier, the map provided a link between towns far distant in temperament as in latitude, but a link less enduring than Whitehead probably wished, for no record exists of it entering the Society’s collections, and it cannot be accounted for.1
Happily, Whitehead’s gift was not a unique specimen. Employed not just to survey Key West but to subdivide it, he had drawn at least one map for each of its four owners. His father William Whitehead, the first proprietor John W. Simonton, Newport’s Pardon C. Greene and John W. C. Fleeming of New Bedford all had copies made for them. Of these, one bearing Fleeming’s name found a place in the collections of Harvard University.2
It is a modestly sized artifact, a mere 17” high by 24” wide, and still smaller relative to its significance, both as a document of Key West’s development and as a plan for how that growth was to unfold. It also happens to be the first example (there are only a few) of such draftsmanship from its creator’s hand.
Whitehead’s “Map of the Town of Key West together with the Island” is in reality two maps sharing space on one page, though not as equals. Nestled in the lower right is an outline of the whole island, hemmed in by the arabesques of the title and a whimsical scroll containing explanatory notes. Over these elements looms the “Town Plot,” the behemoth offspring of its miniature parent, drawn at eight times the scale.
In some ways the smaller map is the more consequential of the two. By plotting the entire perimeter with chain and compass, Whitehead could produce the first accurate portrait of the island before dredging and filling left it drastically altered. He gave a reliable picture, too, of some of the resources available within its outline, especially a large natural salt pond which had long seemed to its owners the best guarantee of its future prosperity.
This map also includes some marks of human intervention in what was still a largely uncharted landscape. A road leading from the Gulf shore afforded access to the salt pond, as did a canal probably used to regulate the intake of sea water.3 Old graves dotted an area of the south beach. Three pairs of dashed lines labeled “Old Avenues” met in the otherwise trackless interior; these probably represent roads cleared during the unpopular U.S. military occupation, which by Whitehead’s time were fast disappearing into wilderness.4 Lastly, on the cape known as Whitehead’s Point stood the first lighthouse, a structure of utmost convenience for the surveyor: its 65-foot tall beacon could be sighted from many places on the island.
The much grander town map is strikingly devoid of such features, for it’s a vision of a future Key West, not a portrayal of the place Whitehead knew. Homes, warehouses and other buildings are invisible. There is little actual human imprint, other than a small road leading to a well and two piers jutting tentatively into the harbor that Captain Matthew Perry christened “Port Rodgers,” a name perpetuated here. Irregular lots follow the arc of the waterfront but the rest of the plan, superimposed even on a tidal lagoon that regularly submerged much of the area east of Front and Whitehead Streets,5 clings to a rectilinear grid such as defined almost all American cities in the nineteenth century.
In real life, of the score of streets laid out here only Front and Whitehead ran for any length. Duval was hardly more than a footbridge over the lagoon, a far cry from the main thoroughfare it would become, and it took years for many of the others to be cleared.6 By projecting a network of mostly hypothetical streets–their names designed to honor the proprietors, the proprietors’ friends and family and a selection of political figures–Whitehead accomplished the real end for which he was hired: that of converting an island owned in common to an array of private parcels.
A few lots remained in the possession of other claimants; these lay mostly along Whitehead and Duval Streets. A handful continued to be held in common or were reserved for public use. But Whitehead marked off the rest of the town into blocks of standard dimensions, each a bit more or less than an acre, and divided the blocks into quarters which he outlined in color. Tracts outside the town limits, including even sections of the salt pond, were tinted according to the same scheme: those allotted to Fleeming wore “a shade of blue,” his father’s lots were coded red, Simonton’s were yellow and Greene’s, predictably, green. The remaining common lands became purple.
The proprietors looked forward to orderly progress and a satisfying return on their investment: it bothered them little that Key West of 1829 “was more pretentious on the map than in reality.”7 Later that year or the year after they paid to have Whitehead’s handiwork engraved. His two maps with their coastlines and other natural features, the street plan and the abstractions of carefully measured blocks and lots all persist in the lithograph. But the scroll has been excised and the calligraphy tamed. A custom house, court house and jail intrude. The blue, red, yellow and green of the original have ceded their places to the letters F, W, S and G. No longer Whitehead’s many-hued vision in pen and ink, Key West has stepped into the future, its map a still remarkable but now colorless standard of reference.
Copyright © 2018-2023 Gregory J. Guderian
 The printed Proceedings of the New Jersey Historical Society 4:3 (1849) 114 record Whitehead’s donation of an “Original MS. Map of the Island of Key West.” This cannot be the copy of the Desobry lithograph now in the collection as Map 661, which was purchased, according to a note on its reverse, in 1967.
 Whitehead later allowed himself the pleasure of boasting to his grandchildren: “the correctness of my survey or of my maps–one being furnished to each proprietor–I never heard questioned.” “Childhood and Youth of W. A. Whitehead 1810-1830.” A transcription of this memoir is held by the Florida History Department, Monroe County Public Library, Key West, Florida, and by the P. K. Yonge Library of Florida History, George A. Smathers Libraries, University of Florida; page 24 of the transcription contains the reference. Harvard Library has generously shared images of its manuscript map both front and back. The verso side reveals that it was given in 1860 by the celebrated abolitionist Senator Charles Sumner, an 1830 Harvard alumnus.
 Walter C. Maloney, A sketch of the history of Key West, Florida (Newark, N.J. 1876) 22-24, provided a short history of salt manufacture on the island, to which Jefferson B. Browne added a description of the function of the canal in Key West, the old and the new (St. Augustine, Fla. 1912) 112.
 Cf. the fourth of the “interrogatories” posed by the proprietors in 1835-36 to several past and present residents of Key West, and their responses, in Congressional Serial Set, H.R. Doc. No. 524, 30th Congress, 1st Session (Washington 1848) 29-38.
 Maloney 49; cf. Browne 10.
 See Browne 11.
 Browne 11.