What race distances can I run in Key West?
Key West has 5K (17), 10K (5), Half Marathon (4). The 5K is usually the easiest entry point if you are new, and the links above jump straight to each distance.
Florida · Race calendar
2026-2027 Running Races in Key West, Florida
Upcoming running races in and near Key West, Florida - 5Ks, 10Ks, half marathons and more, with dates, pricing, finish-time stats, start-line maps, and local run clubs to train with.
19 upcoming races · 9 with finish-time stats
By the numbers
The Biggest and Longest-Running
The Key West races that stand out on the numbers: the biggest field, and the longest unbroken run of editions.
Sun, Sep 20, 2026Healthy Kids Running Series Fall 2026 - Key West, FL Key West, FLFrom $45Details Sun, Oct 11, 2026Southernmost Half Marathon, 10K & 5K Key West, FLFrom $69Details Mon, Oct 19, 2026Fantasy Fest 5K Run/Walk Key West, FLFrom $52Details Sat, Nov 7, 2026Zonta ABC Run/Walk Key West, FLFrom $40Details Sun, Nov 22, 2026Key West Half Key West, FLFrom $45Details Thu, Nov 26, 2026Southernmost Turkey Trot 5K Key West, FLFrom $30Details Sat, Nov 28, 2026Hog Trot 5K Key West, FLFrom $25Details Sun, Dec 6, 2026Montessori Key West 5K Run/Walk & Kids Fun Run Key West, FLFrom $20Details Sat, Dec 12, 2026Rudolph Red Nose Run Key West, FLFrom $50Details Sat, Jan 9, 20272nd Annual Save Our First Responders 5K Key West, FLFrom $30Details Sat, Jan 9, 20272027 Pole Vault in Paradise 5k Key West, FLFrom $30Details Sat, Jan 16, 2027Key West Half Marathon & 5K, 8K, 10K, Rum Stroll & Beer Mile Key West, FLFrom $59Details Sun, Jan 17, 2027Running for Children's Rights to Both Parents Key West, FLFrom $500Register Sat, Feb 13, 2027Cupid's Chase 5K Key West Key West, FLFrom $40Details Sat, Mar 13, 2027Irish Kevin's Shamrock Shuffle 1K/5K/10K 2027 Key West, FLFrom $20Details Sat, May 15, 2027KEYS100 Ultramarathon Key West, FLFrom $240Details Sun, May 30, 2027Salute to Service Key West, FLFrom $40Details Tue, Jun 1, 2027Way Gay 5K Key West, FLFrom $35Details Sat, Jul 24, 2027Hemingway 5K Sunset Run Key West, FLFrom $41Details
How we calculate these stats: RunSesh calculates these figures from the most recent published results of past editions, sourced from RunSignup. We show aggregates only: field size, winning and median times, and the cutoff. We never publish individual finisher tables. Last updated Oct 8, 2026.
Common Questions About Racing in Key West
When is race season in Key West?
November is the busiest month for races in Key West, with 4 of the 19, followed by January with 4. If you are flexible on the date, that is the quickest way to narrow things down.
Are Key West races beginner-friendly?
Yes, for the most part. Across the 9 races in Key West with published results, the typical median finish is around 38:03, which means half of every one of those fields came in slower than that. Recreational runners and walk-runners are the bulk of these fields, not the exception.
Where can I train for a race in Key West?
Browse Key West run clubs on RunSesh to find a training group at your pace.