The Key West Mystique

Key West Island News


Key West Island News connects Key West residents and friends of the island, fosters our One Human Family culture and advances understanding of shared goals for our island community

North Roosevelt Boulevard

North Roosevelt Boulevard | Key West’s last icon of the old days

By Linda Grist Cunningham, editor and proprietor

Linda Grist Cunningham is editor and proprietor of Key West Island News and KeyWestWatch Media LLC. She and her husband, a park ranger at Fort Zach, live in Key West with their Cat 5s.


Next time you’re out on North Roosevelt Boulevard let me know if you see what I see. Nope. Don’t turn your peepers toward the idyllic water views with their mangroves, purdy sailboats and quaint, saggy-baggy houseboats. Instead, eyes opposite to the historic land side.

Yep. Historic. Because if there’s one place on the island that retains its clutch on the old Key West of the 1970s and early ’80s, (heck, even the 1950s in some spots), it’s North Roosevelt Boulevard.

Completed in August 2014, not even the $41.5 million, 2.5-year-long rebuilding of the boulevard‘s three-mile stretch from Eisenhower to the triangle could put a dent in the sheer glory of North Roosevelt’s colorful, unadulterated celebration of the mid-century, concrete retail strip mall of dubious architectural intent.

By the end of the 1930s and into the 1940s, the Overseas Highway connected the mainland to Key West, following the old railroad lines and bypassing the quirky, doglegging, wooden-bridge-connected road that was known as State Road 4A. State 4A snaked through Stock Island following Maloney and MacDonald avenues and reconnecting shortly past them to the old railway lines that became North Roosevelt Boulevard.

We can, in great measure, thank the U.S. Navy and most definitely the state and federal governments for North Roosevelt Boulevard. Those few miles from Stock Island, across the Cow Key Channel and down to where the where Eisenhower used to be the beach are a stupendous testament to just how much dredged fill can be dumped into open water to create a new road and plenty of dry (sorta) land on which to build. And it guaranteed that the Navy could quickly get from its Key West locations to the Boca Chica airbase quickly.

(Side note: It can easily take 30-45 minutes to make the 7.5 miles to Boca Chica from the downtown. Back on April 19, 2018, when then-President Donald Trump briefly visited Key West, it took about 10 minutes, give or take a few. Then, again, the roads were closed except for the motorcade.)

North Roosevelt Boulevard: What to do?

Back to my point: Built on fill with horrifyingly expansive asphalt and concrete parking lots sprawling land side and enough curb cuts to satisfy even the most demanding turning vehicles, while simultaneously unseating users of various pedal and e-powered ancillary devices, North Roosevelt Boulevard is a stunning example of what happens when absolutely everything goes catawampus for almost a century and there’s no architect, planner or, heck, even a drunken, lost tourist with marginal sensibilities to yell STOP.

It’s awful enough to need both crikey AND Mary, Joseph and the Wee Donkey with a side of “what were we thinking.”

Let’s be honest here. No town can do without a retail strip. I don’t care how much you might long for quainter days when there was a neighborhood grocery on the corner and a department store on Duval. All you have to do is look at pictures of Old Town in the middle 20th century to understand that it’s OK to have a retail strip. I am 100 percent delighted that downtown, neighborhood gas stations relocated to North Roosevelt. Plus there’s Home Depot. Like I’d want that in Old Town instead of, say, the Studios of Key West. Or out at Truman Waterfront perhaps?

The city’s got another re-imagining project underway for North Roosevelt Boulevard. The timing is good, assuming Publix is at the table, along with other business owners. Whatever Publix decides to do with the old Searstown property and its second store in the Keys Shopping Center where K mart used to be likely will set the tone for much of the boulevard.

Sure, I’m with most folks. Let’s add housing above the existing single story buildings (though that went no where when Sonic’s owners said “uh, nah; can’t do” and they didn’t.) Heck, who knows if we even could do it. Those are old, concrete buildings, unlikely built to current codes and very likely to be sporting a handsome amount of spalling, not exactly good news for supporting another story or two.

I’m all for landscaping to tone down and blend in the sheer ugly of those massive parking lots. Let’s make sure the responsibility for landscaping maintenance is clarified and unfailingly carried through.

Let’s not, however, turn North Roosevelt Boulevard into a tropical version of suburban Atlanta, a place of no place, with its homogeneous retail strips hidden behind brick walls and trees. North Roosevelt Boulevard is the remaining historic icon of Key West’s actual old days. Let’s find a way to keep that ubiquitous sense of place.


  1. Tommie

    Duval has turned into a retail strip…close your eyes and you could be anywhere USA.
    There is still a mixture of the old and new but there is no reason to have some of those stores…ruins the atmosphere

    • Lloyd

      I like the palm trees that were added.

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