Sugarloaf Key Is Two Keys Wearing One Name, and Fall Is When You Notice
September 3, 2026
September 3, 2026
Look up the address for South of the Seven, the dinner spot inside Sugarloaf Lodge at mile marker 17, and it reads Upper Sugarloaf Key. Look up the old Perky Bat Tower, sitting off the same mile marker a short drive down Airport Road, and the record calls it Lower Sugarloaf Key. Same stretch of highway, same three-digit mile marker, two different halves of the same island. If you have lived here a while, you have probably stopped noticing this. If you are new, it will drive you mildly insane the first time you try to give someone directions.
It is not a typo. It is geography. Sugarloaf Key is shaped like a backward E, and the Overseas Highway crosses it twice, once at Upper Sugarloaf and once at Lower Sugarloaf, with Upper Sugarloaf Sound and Lower Sugarloaf Sound filling the open water between the two arms. That double crossing is the reason the key feels like it has two personalities instead of one, and it is the reason the fall calendar here has one weekend, and only one, when both halves show up at the same docks.
The old State Road 4A, the version of the Overseas Highway that opened in 1927, actually traced the Sugarloaf shoreline along the spine of that backward E before crossing a wooden bridge into the Saddlebunch Keys. Turn oceanside at Mangrove Mama's today and you can still drive a piece of that original road. It runs past the Sugarloaf KOA, dead-ends, then picks back up again down at Lower Sugarloaf, at the end of Sugarloaf Boulevard.
That history explains the modern confusion. You are not imagining that some landmarks a mile apart get filed under different halves of the same key. It is baked into how the road was built.
Here is the rough map, in the order you would actually encounter it:
Two mile markers, one restaurant scene, and a set of landmarks that don't sort as neatly by direction as you'd expect.
Sugarloaf Lodge has been the anchor of that stretch since the late 1950s, when it was built by the Pennsylvania strip mining company that had already dredged and developed much of the key. Lloyd and Miriam Good bought it in 1973 and moved to Sugarloaf Key to run it with their four children, and the property is still controlled by that family through an entity called Miriam BG. Paul Newman and Hunter S. Thompson both reportedly stayed there in its earlier decades, a detail that gets repeated locally more for the flavor than the proof.
In January 2026, the 10.6-acre property, including the lodge, the marina, a pool, tennis courts and the restaurant lease, went on the market for $45 million, with development rights attached to rebuild 24 hotel rooms lost to Hurricane Wilma back in 2005. Whatever happens to the ownership, the restaurant keeps serving. South of the Seven runs dinner Tuesday through Saturday, bar opening at 4:30 for light bites before the kitchen starts at five, and the draw is less the menu changes and more the fixed points on it: a bone-in Tomahawk ribeye big enough to split, a Thai-style whole fried fish, and a patio that catches the sunset over Sugarloaf Sound without much competition for the view.
Down at the marina, the guide culture is what keeps mile marker 17 relevant outside of dinner hours. Captains like Tim Carlile, who runs the Outcast, work the backcountry flats for bonefish, permit and tarpon out of Sugarloaf's docks, the kind of local knowledge that takes years on the water rather than a chart to build.
Three miles up the highway, Mangrove Mama's does the opposite job. Where Upper Sugarloaf's scene skews toward reservations and sunset views, Mangrove Mama's has spent more than 40 years as the place locals actually eat during the week. New owners Jeff Gagnon, Annie van Eller and Beth Connor took over in the past couple of years and were candid about the goal: keep the daily specials real and rebuild the local crowd, not just the tourist one. Gagnon put the location plainly, describing it as a refreshing stop at mile marker 20 between the ditch and the swamp. The old pontoon boat doubling as a live music stage and the new tiki bar out back are additions, but the reason people keep coming back is the same conch chowder and key lime pie reputation the place built decades ago.
Lower Sugarloaf carries the odder landmarks too. The Perky Bat Tower, built in 1929 by a fish lodge owner trying to solve the Keys' mosquito problem by importing bats that promptly flew away and never came back, sat on the National Register of Historic Places for decades until Hurricane Irma toppled it in September 2017. Nearly nine years later, it is still down, and no decision has been made on whether it gets rebuilt. It remains a five-minute detour off Airport Road for anyone who wants to see a genuinely strange piece of Keys history up close.
A short drive past it, Skydive Key West operates out of Lower Sugarloaf's small airport, running jumps from 10,500 feet that locals describe as one of the more scenic drops in the country. And at the end of residential Sugarloaf Boulevard, oceanside, the old jumping bridge on that original 1927 road alignment is still where people go to swim and picnic on a quiet afternoon, water shoes recommended since it's an active waterway and boats do still pass through.
For most of the year, Upper and Lower Sugarloaf run on separate clocks. Upper Sugarloaf's evenings belong to the lodge crowd and the marina regulars. Lower Sugarloaf's days belong to the diner crowd, the skydivers, and whoever's headed to the bridge. The exception is the second weekend of November.
The Sugarloaf Showdown, now in its 13th year, is a catch-and-release tournament for bonefish, permit and barracuda, run by the Lower Keys Guides Association and scheduled this year for November 12 through 14. Registration opened to LKGA members on August 1, with a public window starting August 15 if any spots remain, and last year's tournament filled every available slot in under 48 hours. The entry fee runs $350 per boat, and proceeds from the tournament's auction go to the Guides Trust Foundation, which helps guides who get sidelined by medical issues. As Tournament Director Jessyca LaBadie put it, the event has "always been about more than the fishing."
What that means for anyone living on either half of the key: this is the one weekend when guide trucks and trailers fill shoulder parking from Sugarloaf Marina up through the docks near Mangrove Mama's, when both South of the Seven and Mangrove Mama's see later waits than usual, and when the two separate crossings of this backward E briefly function like one place. If you're not fishing it, the smart move is treating November 12 through 14 the way locals treat any big tournament weekend here: plan errands around it, expect the highway shoulders to be busier than normal near both marinas, and don't be surprised if your usual dinner reservation needs to move up an hour.
The rest of the year, Sugarloaf Key will keep being two keys that share one name and one highway. That's not a flaw in the map. It's just how a backward E works.
If you're weighing what a specific stretch of this key, Upper or Lower, actually offers day to day, Bobby Coe has spent enough time on both sides of mile marker 17 to walk you through it. Schedule a private consultation whenever you're ready to talk specifics.
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