Key West’s Best Fun Runs, Marathons, and 5Ks

Key West might be known for its sunsets and laid-back vibe, but it’s also home to some of the most exciting—and sometimes quirky—races around. Whether you’re a seasoned marathoner or just in it for the fun, these runs offer a unique way to explore the island while giving back. Ever thought about trading your flip-flops for running shoes in paradise? This is your chance to lace up and experience the island like never before with the best runs for 2024-2025.

November 2024

• Zonta ABC Run/Walk (Nov 2, 2024)
  This 5K/10K kicks off in November with fitness and philanthropy to support women’s health programs. The money raised from this event goes to providing important preventive services for women who otherwise cannot afford them. This annual event has changed the lives of many women in the lower keys. Zonta has been able to provide over 3,500 mammograms to local women over the past 31 years and has never turned any woman in need away. Learn more about the Zonta Abc Run/Walk.

• Southernmost Turkey Trot 5K & 1 Mile Rooster Romp (Nov 28, 2024)
  Before you indulge in that holiday feast, burn some calories at this fun Thanksgiving 5K! The Southernmost Turkey Trot benefits Reef Relief, a local non-profit focused on preserving the coral reef ecosystem. Gobble your way through this family-friendly event and start the holiday off right. Learn more about the Southernmost Turkey Trot 5k here.

• Hog Trot 5K Run/Walk (Nov 30, 2024)
  Are you planning to celebrate Thanksgiving in Key West? If so, get ready to run off that Thanksgiving feast at the Hog’s Breath Saloon Hog Trot 5K Run/Walk! Join us for a fun 5K through Old Town Key West, all in support of one of our favorite local nonprofits: Reef Relief. Learn more about this fun run here.

December 2024

• A Positive Step of Monroe County Rudolph Red Nose 5K Run/Walk (Dec 14, 2024)
  Don your reindeer antlers and hit the pavement! This holiday-themed race supports at-risk youth programs, giving back to the community while spreading festive cheer. Whether you walk, run, or prance, it’s a jolly way to enjoy Key West’s December sunshine. Register here.

• Running of the Elves 5K (Dec 21, 2024)
  Are you ready to get your Elf on this holiday season? Grab your festive holiday costumes and Run, Jog, Stroll, or Jingle all the Way to the finish line! The 1st Annual Running of the Elves 5K and Jingle Bell Mile is set to spread holiday cheer while benefitting Reef Relief. Learn more about this event here.

January 2025

• Key West Half Marathon & 5K (Jan 18-19, 2025)
  Want a race with serious bragging rights? The Key West Half Marathon attracts runners from all over the globe. Whether tackling the 5K or the half marathon, you’ll be racing through waterfront views, with proceeds supporting local youth sports. It’s the perfect way to kick off your New Year’s fitness goals! Sign up here. Photos courtesy of Key West Half Marathon.
  

February 2025

• Cupid’s Chase 5K (Feb 8, 2025)
  Fall in love with running this Valentine’s Day at the Cupid’s Chase 5K, which benefits people with disabilities through Community Options, Inc. Whether you’re running solo, as a couple, or with friends, this race is all about heart—literally. Sign up here. 

April 2025

• 44th Annual Seven Mile Bridge Run (April 5, 2025)
  You’ve never experienced a run quite like this. The Seven Mile Bridge Run takes place entirely over water on the famous Seven Mile Bridge, with sweeping ocean views. This is one of the most exclusive races in the Keys, so snag your spot early and prepare to be wowed. Proceeds benefit local youth programs in the Middle Keys. Registration details will be available soon—stay tuned for updates by visiting the official race site.

May 2025

• KEYS100 (May 17, 2025)
  Ready to push your limits? The KEYS100 is not for the faint of heart. This 100-mile ultra-marathon (with relay options) takes runners from Key Largo all the way to Key West. It’s a grueling yet rewarding journey, and proceeds support the Cancer Foundation of the Florida Keys, making every mile meaningful. Sign up here. 

June 2025

Big Gay 5K (June 28, 2025)
Celebrate Pride with a burst of energy at the Big Gay 5K! This colorful race promotes LGBTQ+ equality and inclusion, with plenty of fun along the route. It’s an uplifting event that embodies the free spirit of Key West while supporting LGBTQ+ organizations. Learn more about this event here.

July 2025

• Hemingway Sunset Run (July 26, 2025)
  What better way to honor Key West’s most famous resident, Ernest Hemingway, than with a 5K at sunset? This race is a traditional part of Key West’s annual Hemingway Days celebration and salutes the life and work of the author who lived and wrote on the island in the 1930s. Did you know Southernmost Beach Resort and Southernmost Beach Café are proud sponsors of the Hemingway 5K Sunset Run, and the registration and awards beach party are happening right here at our resort?  Event details can be found here. Photo courtesy of Hemingway 5k & Paddleboard Race.

While some 2025 events are not listed yet, other runs will pop up on the calendar as the year progresses. To stay updated, make sure to check race listings on sites like Running in the USA or look into the Southernmost Runners Club. This club supports running programs in Key West and is something you might want to consider joining if you visit often and love to run. 

After crossing those finish lines, there’s no better place to unwind than at our Key West Beach Resort. Whether you’re cooling off by the ocean, taking a dip in the pool, or toasting to your accomplishments, we’ll be your perfect home base as you run, relax, and soak up all that Key West has to offer. #somolife