The balmy weather and open horizons make the Florida Keys a special spot for marathons, 5K’s, and the like. If you’re a newcomer to running and are set on a 5K, or looking for a high intensity marathon or even a 100-mile race, there’s something for all runners in Key West. Here are some of our favorite marathons, runs, 5Ks, and walks across the Keys.

Key West Half Marathon & 5K

13.1 mi. or 5K

Everyone loves this marathon for the usual reasons - and to make it totally Key West, the finish line is at the Half Shell Bar, one of the island’s most popular seafood restaurants. With 4,000 participants, the Key West Half Marathon and 5K course runs the Florida Keys Overseas Heritage Trail, offering excellent ocean views that make your January run all the more sweeter.

When: January

Seven Mile Bridge Run

6.8 mi.

The most famous run in the Keys, the Seven Mile Bridge Run started in 1982 and takes place each spring in the Lower Keys. Completely surrounded by water from start to finish, the run has a limited 1,500 spots, all of which are filled almost immediately once registration opens!

When: April

Benefits: Local youth of the Middle Keys, both at the local schools as well as other youth groups which promote athletically oriented activities. Since the inception of the run, Middle Keys’ kids have benefited from donations of well over $500,000 distributed by the organizers of the Seven Mile Bridge Run, the Marathon Runners Club.

[3 Scenic Running Routes in Key West]

Cow Key Channel Bridge Run

0 mi.

The world’s first zero-K was created in response to the grueling Seven Mile Bridge Run! Measuring about 300-feet long, the Cow Key Channel Bridge near Key West is one of the shortest in the Florida Keys, so it makes sense to host the event there. Participants dress in cow costumes as they compete for the Golden Calf Awards (for fastest and slowest runner), and take advantage of the free rum shots and Botanical Garden Beer Bash at the finish line. The Cow Key Channel Bridge Run is purely for fun, for athletes and non-athletes alike.

When: April

Benefits: A portion of the proceeds benefit the Monroe County Sheriff’s Animal Farm on Stock Island. To date, the run has raised over $10,000 for the animals in need.

Keys100

100 mi., 50 mi., or 50K

The fun thing about Keys100 is its versatility. The 100-mile can be run individually or in teams of up to six, each taking on their leg of the run. The 100-mile starts in Key Largo; 50-mile (up to three participants) in Marathon; and 50K in Big Pine Key. All races end at Higgs Beach in Key West. Stay for the after party under the tent, for an awards ceremony, food, beer, and a free "Sol Yoga Post-Race Recovery" session. 

When: May

Benefits: The Cancer Foundation of the Florida Keys in support of their educational work and outreach, free screenings, and direct support of cancer patients and their families throughout the Keys.

[Swim, Bike, Run Key West]

Hemingway 5K Sunset Run and Paddleboard Race

5K run, 3 mi. paddleboard race

Ok, these 100-mile marathons are great, but where’s the family-friendly, fits-all-sizes run? The Hemingway 5K Sunset Run and 3-mile Paddleboard Race is for anyone, as it can be walked, skipped, or ran, and goes through Old Town and along the Key West waterfront. The event is part of Hemingway Days, commemorating the late great author, Key West resident, and character. Rent your paddleboard in advance. See the list of paddleboard vendors on the events details page.

When: July

Southernmost Marathon (or SoMa Marathon)

13.1 mi. or 10K

This flat-terrain half marathon or 10K begins and ends at Higgs Beach, but still requires its share of preparation and conditioning. The SoMa Marathon is internationally famous for its iconic landmarks, ocean views, and excellent fall weather.

When: October

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Grab your running shoes and meet us at The Gates Hotel in Key West. We have shuttle service to and from Old Town, on-site dining options, and our pool area is one of the best on the island. See our special offers, which include exclusive rates for Florida residents. Now for a limited time, residents receive up to 20% off our best available rate, free parking, and two welcome cocktails with our Florida Residents Escape package.

That’s not all. When you stay with The Gates Hotel you’ll have access to our Running Maps that provide the best routes for a 5K, 10K, or a leisurely stroll, with some popular selfie stops along the way. Plus, our Bootcamp in a Box, a self-guided instructional workout that gives you a full body workout with minimal equipment.