Featured by Runner’s World as one of the Best 5Ks to Run this Summer. Details: Back for our 37th year! Runners and walkers enthusiasts can test their skills and celebrate Ernest Hemingway’s sporting lifestyle by joining us in the Conch Republic on July 25-26, 2026 during the in-person Hemingway 5k Sunset Run/Walk! The athletic challenges are part of Hemingway Days, a six-day commemoration of the life and work of the author who lived and wrote in Key West for most of the 1930s. All participants will start and finish at the iconic Southernmost Point buoy! Be sure to plan to spend time at our famous after party on the beach! Don't Forget to Run or Watch the Beer Mile on Sunday! The most fun event of the week-end! 12PM.
| Distance | Price | Opens | Closes |
|---|---|---|---|
| 3.1 Miles | $39.99 | Jul 28 | Aug 30 |
| $43.00 | Aug 31 | Sep 30 | |
| $46.00 | Oct 1 | Oct 31 | |
| $49.00 | Nov 1 | Nov 30 | |
| $52.00 | Dec 1 | Dec 31 | |
| $55.00 | Jan 1 | Jan 31 | |
| $58.00 | Feb 1 | Feb 28 |
| Year | Finishers | Median Time | Fastest Time |
|---|---|---|---|
| 2023 | 368 | 31:56 | 17:49 |
| 2022 | 374 | 33:10 | 15:39 |
| 2021 | 318 | 35:36 | 16:01 |
| 2019 | 494 | 35:12 | 17:19 |
| 2018 | 569 | 35:29 | 18:28 |
| Year | Finishers | Median Time | Fastest Time |
|---|---|---|---|
| 2019 |
Interested in this race?
| $61.00 | Mar 1 | Mar 31 |
| $63.00 | Apr 1 | Apr 30 |
| $65.00 | May 1 | May 31 |
| $67.00 | Jun 1 | Jun 30 |
| $67.00 | Jul 1 | Jul 24 |
| 5K | $39.99 | Jul 28 | Sep 30 |
| $43.00 | Oct 1 | Nov 30 |
| $46.00 | Dec 1 | Dec 31 |
| $49.00 | Jan 1 | Jan 31 |
| $52.00 | Feb 1 | Feb 28 |
| $55.00 | Mar 1 | Mar 31 |
| $58.00 | Apr 1 | May 31 |
| $61.00 | Jun 1 | Jun 30 |
| $63.00 | Jul 1 | Jul 25 |
| Beach n Beer Mile (In-Person Event) | $37.00 | Jul 28 | Aug 30 |
| $39.00 | Aug 31 | Sep 29 |
| $41.00 | Sep 30 | Oct 30 |
| $45.00 | Oct 31 | Feb 27 |
| $47.00 | Feb 28 | Apr 29 |
| $48.00 | Apr 30 | Jun 29 |
| $50.00 | Jun 30 | Jul 26 |
SATURDAY, JULY 25, 2026 – RACE DAY! 3:00 pm – 7 pm: Race Registration Booth Location: Outside Southernmost Beach Cafe, 1405 Duval Street 7:30 pm: Start of 5K Run/Walk Location: Southernmost Point 8:00 pm – 10 pm The Awards/Beach Party featuring Tastings of Papa’s Pilar Rum, Islamorada Beer and Snacks, raffles and entertainment by Island Steel Drum Player Ivan Bertie!! Location: Outside Southernmost Beach Cafe, 1405 Duval Street Inside will be extended happy hour and select menu specials till clo
| 77 |
| 1:05:45 |
| 36:48 |