Drive the Overseas Highway through Cudjoe Key at dinnertime and you will pass the restaurant most people mean when they say "let's eat on Cudjoe." You might not notice the other two worth knowing at all. One sits behind the Sheriff's substation on a residential side street. The other faces a stretch of Old State Road that most through-traffic never turns onto. Neither is located on the Overseas Highway.
That is the actual shape of eating on this key, and it is worth understanding if you live here: the four places have different settings, hours, and seasonal offerings.
The One Address Everyone Means
Say "Cudjoe" and "restaurant" in the same sentence to a Lower Keys local and they will assume you mean the building at Mile Marker 22.5 oceanside, 22658 Overseas Highway. Downstairs is Square Grouper Bar & Grill. Upstairs, reached by a separate staircase, is My New Joint 420 Lounge. Same roof, two different nights out.
Square Grouper has been run by owner Lynn Bell for more than sixteen years, long enough that the seafood stew and the Certified Angus ribeye are the kind of order regulars stop reading the menu to make. The key lime pie carries a nod from the Wall Street Journal. The track record was strong enough that Bell's operation expanded off-island, first to a converted boathouse at the Islamorada Marina in 2019, run day to day by her children Joe and Sarah, and later to Key West, where the old PT's Late Night space on Caroline Street became a third Square Grouper.
None of that changes what the Cudjoe location does every year without fail. Its own listing spells out the schedule plainly:
"We close for the month of September and re-open Thursday before Columbus Day weekend."
That month-long closure accounts for the empty lot each September. If you are new to the island, keep the annual break in mind when planning a visit.
Upstairs Runs on a Different Clock
My New Joint 420 Lounge opened in the space above Square Grouper in 2015 and has seasonal offerings. The raw bar serves stone crab claws only during the official season, October 15 through May 15, alongside fresh shucked oysters and peel and eat shrimp year-round. Happy hour runs 4:20 to 6:30 with live music from six to ten.
Two Places Off the Highway
Half a mile off U.S. 1, tucked behind the Sheriff's substation on Drost Drive, sits The Bent Prop Bar and Grille. Co-owners Chuck Miller and Carolyn Butler bought the building, a former community clubhouse that had sat gutted by fire and vacant for years, and rebuilt it themselves down to the plumbing and electrical, since it had never even been connected to the county sewer system. The result is a bar and dining room that overlooks the water and serves lunch and dinner Wednesday through Sunday, but you will not see it from the road. You have to already know Drost Drive exists.
Broil, the steakhouse on Old State Road 4A, is small, family-owned, and built around wood-fired, in-house cut steaks with scratch-made sides and a carrot cake made from what the owners describe as their great-grandmother's recipe. It is open for dinner only, five to nine most nights, and the people who run it are usually the same people walking the floor checking on tables. Together, the two offer a waterfront bar and a wood-fired steakhouse.
What This Actually Looks Like on a Given Week
For anyone still getting their bearings on where things are:
- Square Grouper Bar & Grill, MM 22.5 oceanside, lunch and dinner Tuesday through Saturday, closed all of September
- My New Joint 420 Lounge, same building, upstairs, opens at 4:20 p.m. Tuesday through Saturday, stone crab available October 15 through May 15
- Broil, Old State Road 4A, dinner only, five to nine most nights, wood-fired steaks and homemade desserts
- The Bent Prop Bar and Grille, Drost Drive off U.S. 1, lunch and dinner Wednesday through Sunday, waterfront bar
Use the list as a quick guide to addresses and hours before heading out.
More About These Four Restaurants
The four restaurants differ in location and schedule. Square Grouper has expanded to Islamorada and Key West. Bent Prop and Broil are located away from the Overseas Highway, and My New Joint serves stone crab during the season described above.
Knowing their locations and schedules can help you plan a meal around your time on Cudjoe Key.
If you already know these places, none of this is news. If you are getting oriented to this stretch of the Lower Keys for the first time, whether you are settling in permanently or just learning the rhythm of a place you visit often, it helps to know where the restaurants are located.
For anyone thinking about property on Cudjoe Key or elsewhere in the Middle and Lower Keys, Ally Kelley works this stretch of the island chain daily and can walk you through what life actually looks like on any given key, not just what shows up in a listing photo. Request a private consultation to start the conversation.
