More than 400 runners and walkers crossed the finish line each year at Key West’s Southernmost Marathon and Half Marathon, which takes runners along the shoreline of — just as its name suggests — the southernmost point in the contiguous United States, here along the tip of South Florida, roughly 90 miles across the Gulf of Mexico from Cuba.
Southernmost Half Marathon and 10K
October 12, 2025
Key West
Road
Ready to sign up?
100-500
Fast & Flat
Oceanfront
High: 86°
/ Low: 77°
Runners and walkers — the half marathon is open to both — will start the out-and-back course for the race near the western end of the island, at the Rum Barrel Bar & Restaurant at Front Street and Simonton Street. From there, the half marathoners and the full marathoners will follow the same course for roughly the first 7 1/2 miles, heading around the western and southern edges of the island to U.S. 1.
The first few miles of the race — which is virtually all flat throughout, and never higher than a few feet above sea level — take runners through Key West’s Old Town neighborhood, where most of the tourist attractions and signature Key West-style architecture can be found, everything from restored wooden homes with lush tropical trees and plants growing outside to the Ernest Hemingway House, where the legendary author lived throughout most of the 1930s.
After reaching the end of South Street they’ll be at the actual location of the Southernmost Point of the continental U.S., a giant red, black and yellow bullet-shaped landmark that’s pretty impossible to miss.
Next, the course heads to Higgs Beach and then to South Roosevelt Boulevard, which will take runners for the next few miles to the intersection with U.S. 1. The course keeps going from there, though, turning right and across the Overseas Bridge and running the length of nearby Stock Island before reaching the turnaround point.
Once they make the turnaround, runners recross the bridge, this time turning right again and running the top half of the island before crossing the finish line on Front Street.
Overview
More than 400 runners and walkers crossed the finish line each year at Key West’s Southernmost Marathon and Half Marathon, which takes runners along the shoreline of — just as its name suggests — the southernmost point in the contiguous United States, here along the tip of South Florida, roughly 90 miles across the Gulf of Mexico from Cuba.
Course Description
Runners and walkers — the half marathon is open to both — will start the out-and-back course for the race near the western end of the island, at the Rum Barrel Bar & Restaurant at Front Street and Simonton Street. From there, the half marathoners and the full marathoners will follow the same course for roughly the first 7 1/2 miles, heading around the western and southern edges of the island to U.S. 1.
The first few miles of the race — which is virtually all flat throughout, and never higher than a few feet above sea level — take runners through Key West’s Old Town neighborhood, where most of the tourist attractions and signature Key West-style architecture can be found, everything from restored wooden homes with lush tropical trees and plants growing outside to the Ernest Hemingway House, where the legendary author lived throughout most of the 1930s.
After reaching the end of South Street they’ll be at the actual location of the Southernmost Point of the continental U.S., a giant red, black and yellow bullet-shaped landmark that’s pretty impossible to miss.
Next, the course heads to Higgs Beach and then to South Roosevelt Boulevard, which will take runners for the next few miles to the intersection with U.S. 1. The course keeps going from there, though, turning right and across the Overseas Bridge and running the length of nearby Stock Island before reaching the turnaround point.
Once they make the turnaround, runners recross the bridge, this time turning right again and running the top half of the island before crossing the finish line on Front Street.
