The ultimate ‘linear city’

In a long drive down the Overseas Highway, Charles Critchell explores the peculiar experience of an elongated island city: the Florida Keys

Illustration by Nate Kitch

Under the auspices of a southern sky, the road ahead of us unwound invitingly as Miami’s Downtown buildings and tangle of free-ways steadily receded from view. The palpable sense of escape which comes from shrugging off any big city is often compounded by the adventure of what lies ahead – in our case the one hundred mile length of the Florida Keys, starting in Key Largo and finishing in the fabled Caribbean Island that is Key West, very much the end of the road in all senses.

Along with its celebrated cousins, the heroic Route 66 and scenic Pacific Coast Highway, Florida’s own Overseas Highway provides the backdrop to one of the great American Road trips. Whereas those other routes intermittently range from perfect isolation to expansive urban vistas, The Overseas Highway presents a very different dynamic. Considering its location on such a seemingly remote string of islands, it is in fact well populated for much of its length, a tribute to the road’s importance in facilitating the growth of not only a plethora of neighbourhoods and businesses but the critical ancillary infrastructure needed to support it. It soon becomes apparent that the Overseas Highway is much more than an expansive ribbon of tarmac, but a linear city – a one hundred mile long High Street.

The development of the Overseas Highway came into being in the early twentieth century, though it was not then known as such – or even recognised as a continuous Highway. Like many road networks throughout America the route was a palimpsest of an earlier railway network, The Florida Overseas Railway. The Railway was the creation of businessman Henry Flagler’s fertile mind – the man credited as the ‘Father of Miami’ – and was envisaged to be both a key artery in prizing open Latin American markets south of Key West’s deep water port, as well as a pleasure line for wide-eyed tourists and all the opportunities of the 1920s Florida land boom.

What becomes immediately evident as you leave Miami’s wide ubiquitous boulevards and join the confluence of traffic headed South is that this road is one of business as much as it is pleasure, as wide-bodied tankers and goods trucks happily trundle along behind open top hire cars and weathered family station wagons. The two lane highway is certainly more than the sum of its parts; the thread by which a myriad of ecologies, communities and businesses hang off – dependent on its passing trade for their survival.

Strip mall, Florida Keys style

Lining the route are a proliferation of different building typologies – most comprise simple concrete or clapboard structures alongside gaudy service station architecture. It is however the repetition of three key building types – gas stations, banks and churches – which speak of the trade off the Keys has had to make between commerce and community. Head away from the main road and these communities begin to reveal themselves; from discount outlet warehouses and shiny new condos clustered around small newly developed business parks and marinas in the upper Keys, to the family-run and fiercely independent small traders and long established residential neighbourhoods in the mid and lower Keys.

Much like the typical High Street, the character of the built fabric inevitably varies as you venture further, though the juxtaposition of the mundane alongside the sublime serves as a constant reminder that this very much a functioning strip of city.

One of the major pulls of the journey south is the passage alongside the infamous Seven Mile Bridge, which straddles the middle and lower Keys. Though hailed as the eighth wonder of the world at the time of construction, it claimed the lives of over seven hundred labourers before being largely destroyed as a result of the1935 Labour Day Hurricane. The original superstructure exists today as a disused and decaying concrete deck, idling atop a mass of staunch pilings only meters above the placid Gulf.

You could be forgiven for missing it entirely though, as the roadway motorists now travel along exudes a drama all of its own; climbing steadily you are soon seemingly thrust headlong into the oncoming clouds as the water to either side drops away and the impression of speeding in some otherworldly domain takes hold for just a few seconds.


Aside from this welcome digression, the steady procession of vehicles runs pretty much the full one hundred mile length of the keys, all reined in by the variable 35-55 mile per hour speed limit, which ensures the road can fulfil its function as a souped-up sidewalk.

The speed limit dictates that you window shop as you travel the road, giving businesses the opportunity to vie for your attention whether it be for a burger or a tank of fuel. Not all businesses fare so well however, as rust-ravaged billboards and derelict motels are interspersed throughout, simply left to bake in the incessant Floridian sun.

Indeed the effect of an extended drive seemingly sandwiched between sun and sea gives way to a condition locals call ‘island time’; the idea of embracing a more leisurely pace not to be found on the mainland. To this end I believe that it is in fact a new form of ‘city time’ particularity in the vicinity of the highway itself, as all the cues of urban life remain; the labourers toiling amid mounds of earth at the side of the road, or the gleaming red fire truck and sheriffs patrol car – both ready to be despatched at a moment’s notice.

The figurative downtown of this linear city is without doubt Key West, a seemingly self-governing principality known for its loose morals and hedonistic wants. Here the Overseas Highway tightens into a knuckle of romantically named boulevards and side streets as the familiar American grid re-asserts itself. The clamour of activity and industry soon thrusts itself upon you as the linear cities strip malls and stirring panoramas are replaced with a dense web of telegraph poles, street signage and a canopy of vegetation. The diversity of sights and experiences which the Highway presented us with confirms my belief that it is very much a city in every aspect, and one that despite running in a straight line, is in no way predictable.

Key West
Key West

All photographs by Charles Critchell


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