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


Key West’s Mallory Square | What happens when history, nostalgia and cash collide?

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.


Mornings are unkind to Key West’s Mallory Square.

Even after a night’s rain, there’s a lingering oops-I-overserved-myself on the humid breeze. The detritus of last night’s Sunset Celebration is stacked in any ol’ available corner and the city workers are swabbing down those public restrooms.

The shops with their imported tchotchkes, shells and coozies aren’t quite open. The Conch Train’s not ready for its first passengers. The Waterfront Playhouse is buttoned up. Roosters hustle their hens and broods across the brick pavers in search of leftovers in the cracks.

For 20 hours a day, Mallory Square, the (depending on the historical source) namesake of a slave-holding, sailor flogging founding father, and one of Key West’s most valuable chunks of real estate, is a tattered, undisciplined, sprawling warren of miscellaneous stuff and trash cans.

(An aside about the name Mallory Square: Some folks are convinced the square was named after Ellen Mallory or her son, Stephen Mallory, a U.S. Senator, slave holder and Secretary of the Navy for the Confederacy. Historians and the Old Island Restoration Foundation say that the square was named after the Mallory Steamship Company out of New England. Over the years, the actual namesake has been conflated and forgotten.)

Until 2020, when Covid-19 jammed the brakes on docking cruise ships and Key West voters said “no more,” there wasn’t even a decent view off the Mallory Square pier of the island-of-the-rich-and-famous, Sunset Key, aka Tank Island.

Then comes sunset. With all eyes turned west, Mallory Square becomes a bucket-list contender as locals stand shoulder to shoulder with visitors from around the world to watch the sky cycle through the color wheel, amid cries of “I saw it. The green flash. I saw it.” Whether they did or not is irrelevant.

Key West long ago laid claim to sunset. And, though I’m here to tell you there are spectacular sunsets in a corn field along Interstate 39 in Illinois, there’s no place on earth that celebrates as well and as consistently the sheer joy of sunset like Key West. With its musicians, performers, cats, fire sticks, fortune telling, dog collars and street food, Mallory Square’s sunset celebration is esprit de corps on steroids.

So it makes sense that every couple of decades folks get together and wonder how they can fix up the place. If you’re a bit short in the memory department, until the late 1990s, Mallory Square was mostly a gigantic parking lot with some stuff tucked in and around. Re-imagining efforts in the late 1980s and again in the late 1990s gave us renovated buildings, brick pavers, more trees, some seating and a mightily reduced parking lot.

Mallory Square on a September morning

Mallory Square | How the process works

In 2021, the City of Key West hired Sasaki, the award-winning Boston architectural design firm, to research and develop a long-range master plan for redeveloping Mallory Square and the Sunset Celebration. Its report to the city, which included extensive community input, listed four areas in need of significant improvement: lighting, seating, shade and signage.

As I read through the detailed project plan, it was clear that any improvements to the immediate area around the Sunset Celebration would be dependent on a far more extensive and holistic redesign of the entire Mallory Square district, which includes Meson de Pepe, Historic Tours of America, the Waterfront Playhouse, the Cultural Preservation Society and the Key West Art Center in addition to the city-owned spaces.

So this month, the city began another round of community research to build on the Sasaki findings. Over the next nine months, the city and Sasaki will research and develop a master plan for Mallory Square. That plan is expected by May 2023.

Some of this will be typical low-hanging fruit. More shade. More places to sit. Public restrooms that don’t feel (and smell) like dungeons. Less clutter in the corners. Those are, indeed, most needed, but they’re not the hard stuff.

The hard stuff’s going to rear ugly when we decide if the Mallory Square district, including the sunset square, is going to be a major, commercial tourist destination or an open space park. Either approach can be designed beautifully to maintain the funkiness of the nightly Sunset Celebration.

But what happens the rest of the day, those remaining 20 hours, will depend entirely on whether we’re going to make money at Mallory Square by enticing folks down there all day for food, shopping, entertainment, pier fishing and recreation — or whether we’re going to develop a passive, open space park that encourages wandering, walking, sea gazing or perhaps setting up an easel or reading a book in the shade.

You can have your say on which ways we go by completing the online survey. Your responses go directly to the Sasaki group. The survey ends Oct. 5 and is divided between visitors and residents. Put down your coffee and let your voice be heard. (

Here’s how I’m leaning:

  • I don’t want to see significant incursions on today’s open space, but a passive park is boring and won’t get me back to the square very often.
  • I certainly don’t want a bunch more souvenir shops or national chains. I’m good with local artists and locally-owned businesses.
  • Not sure how I feel about a ring of food trucks, though food and snacks other than Pepe’s would be a plus to encourage return visits to just sit and enjoy the open water.
  • I’m OK with getting rid of all the parking and making the entire district accessible and pedestrian friendly.
  • Fishing from the pier sounds heavenly — until I remember someone’s going to set up shop to rent poles and bait. Don’t want vendors for chairs either. Bring your own or not at all.
  • Fixing all the streets around and into the Mallory Square district would be welcome. Getting rid of all motorized and electric vehicles would be perfect.
  • I’m good with permanent shade structures as long as we add more green growing stuff. I don’t think a bunch of shade trees is the answer.
  • I do not want the square to mimic Chicago’s Navy Pier or the harbor area in Baltimore. Please no Ferris wheels and such.
  • Keep the actual Sunset Celebration old-fashioned funky like it’s always been. Local performers, artist and vendors, please.
  • Lest it go unsaid: We need to change the name or install a significant “monument” that explains the rarely-mentioned biography of Stephen Mallory. I’m usually not a name-changing fan and prefer we openly share rather than erase history. Mallory was a slave holder who was Secretary of the Navy for the Confederacy. He got around the restriction that slave holders could not become U.S. Senators by putting his slaves in a trust controlled by his brother-in-law. After the Civil War he was imprisoned for treason. He did not repent.
  • I sure as heck don’t want Mallory Square to look toward the South Beach “park” as a role model.


  1. Kamerran Zilakakis

    Please DO NOT change the name! It’s Mallory Square – if people don’t like the name or believe it represents something they don’t support, then they have the choice not to visit. Leave Mallory Square alone, as-is, but if you must update it, provide some shade and some seating that can’t be monopolized by homeless, but enjoyed by locals and tourists alike. We have enough restaurants, bars and shops all over Key West. Please let this be a place for the nightly celebration and a peaceful place to visit during the day.

  2. Sharon wells

    I will dig out my report on history of Mallory Sq done some years ago

  3. Sharon wells

    This is excellent , z Linda. I couldn’t agree more.
    I fear overdone efforts.

    More shade, way less parking and
    Only select food vendors.
    I have not even visited in a decade.
    Keep it simple!

    • Linda Grist Cunningham

      Thanks, Sharon. I know you understand this way better than I, so your comments mean a lot. Would love to read your report.

  4. B Hockaday

    I do miss Key West of the 70’s . It has been our winter vacation since then . When places are loved for how they are and becomes a fabulous place to visit and tourist brings in huge revenue then the powers that be want to change it . They don’t get it , we love the original .

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