Running Races in Key West, Florida
19 upcoming races in Key West, updated nightly. For radius search from your exact zip, use the Race Finder.
Racing in Key West: what the calendar looks like
There are 19 upcoming races on the Key West calendar over the next 12 months, with race dates in 10 of the next 12 months. January is the busiest month, with 4 races. By race count, Key West ranks 18th among Florida cities.
Of those, 14 offer a 5K, 5 offer a 1 Mile and 5 offer a 10K. The next half marathon is Southernmost Half Marathon and 10K on October 11. Where fees are published, the median entry in Key West is $40, above the Florida median of $30.
Races by month
- Sep 20261 race
- Oct 20263 races
- Nov 20263 races
- Dec 20261 race
- Jan 20274 races
- Feb 20271 race
- Mar 20271 race
- May 20273 races
- Jun 20271 race
- Jul 20271 race
September 2026
- Sat 9/5Parrots and Margaritas 5K Run/WalkKey West, FL · 5K · 1 Mile · from $40 · register ↗
October 2026
- Sat 10/3Duval MileKey West, FL · 1 Mile · from $30 · register ↗
- Sun 10/11Southernmost Half Marathon and 10KKey West, FL · Half Marathon · 10K · from $59 · registration closed · register ↗
- Mon 10/19Fantasy Fest 5K Run/WalkKey West, FL · 5K · 1 Mile · from $42 · register ↗
November 2026
- Sat 11/7Zonta ABC Run/WalkKey West, FL · 5K · 10K · from $40 · register ↗
- Thu 11/26Southernmost Turkey Trot 5KKey West, FL · 5K · 1 Mile · from $25 · register ↗
- Sat 11/28Hog Trot 5KKey West, FL · 5K · from $25 · register ↗
December 2026
- Sat 12/12Rudolph Red Nose RunKey West, FL · 5K · from $50 · register ↗
January 2027
- Thu 1/7Pole Vault in Paradise 2027Key West, FL · from $75 · register ↗
- Sat 1/92nd Annual Save Our First Responders 5KKey West, FL · 5K · from $25 · register ↗
- Sat 1/16Key West Half Marathon & 5K, 8K, 10K, Rum Stroll & Beer MileKey West, FL · Half Marathon · 5K · 8K · 10K · 1 Mile · from $40 · register ↗
- Sun 1/17Running for Children's Rights to Both Parents - 13 of 50 Half Marathons in 50 States - FloridaKey West, FL · Half Marathon · 5K · 10K · from $40 · register ↗
February 2027
- Sat 2/13Cupid's Chase 5K Key WestKey West, FL · 5K · from $40 · register ↗
March 2027
- Sat 3/13Irish Kevin's Shamrock Shuffle 1K/5K/10K 2027Key West, FL · 5K · 10K · 1K · from $20 · register ↗
May 2027
- Sat 5/8Key West Paddle Classic 2027Key West, FL · 12 Miles · 4 Miles · from $70 · register ↗
- Sat 5/15KEYS100 UltramarathonKey West, FL · 100 Mile · 50 Mile · 50K · from $240 · register ↗
- Sun 5/30Salute to Service presented by The Marker ResortKey West, FL · 5K · from $30 · register ↗
June 2027
- Tue 6/1Way Gay 5KKey West, FL · 5K · from $35 · register ↗
July 2027
- Sat 7/24Hemingway 5K Sunset RunKey West, FL · 5K · from $37 · register ↗
Where to stay in Key West
Race-weekend hotel search, dates prefilled for check-in the night before.
- Oct 11Southernmost Half Marathon and 10KFind hotels for this race weekend
- Jan 16Key West Half Marathon & 5K, 8K, 10K, Rum Stroll & Beer MileFind hotels for this race weekend
- Jan 17Running for Children's Rights to Both Parents - 13 of 50 Half Marathons in 50 States - FloridaFind hotels for this race weekend
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Planning a race
- Getting inlotteries, qualifiers, and how entry works for the races that sell out
- Lottery watchwhich race lotteries and registration windows are open right now
- Choosing a first marathona practical guide to picking a debut race