Running Races in Key West, Florida
17 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 17 upcoming races on the Key West calendar over the next 12 months, with race dates in 8 of the next 12 months. Among complete calendar months, January 2027 has the most listed races, with 5. By race count, Key West ranks 28th among Florida cities.
Of those, 14 offer a 5K, 4 offer a 1 Mile and 3 offer a 10K. The next half marathon is Key West Half Marathon & 5K, 8K, 10K, Rum Stroll & Beer Mile on January 16. Where fees are published, the median entry in Key West is $37, above the Florida median of $30.
Races by month
- Nov 20262 races
- Dec 20263 races
- Jan 20275 races
- Feb 20271 race
- Mar 20271 race
- Apr 20271 race
- May 20273 races
- Jul 20271 race
November 2026
- 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
- Sun 12/6Montessori Key West 5K Run/Walk & Kids Fun RunKey West, FL · 5K · 1 Mile · from $20 · register ↗
- Sat 12/12Rudolph Red Nose RunKey West, FL · 5K · from $50 · register ↗
- Sat 12/19Running of the Elves 5K Run/Walk & Jingle Bell MileKey West, FL · 5K · 1 Mile · from $35 · register ↗
January 2027
- Thu 1/7Pole Vault in Paradise 2027Key West, FL · from $75 · register ↗
- Sat 1/92027 Pole Vault in Paradise 5kKey West, FL · 5K · from $30 · 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 · 5K · 8K · 10K · Half Marathon · 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 ↗
April 2027
- Sun 4/25Key West HalfKey West, FL · Half Marathon · 5K · from $45 · registration closed · register ↗
May 2027
- Sat 5/8Key West Paddle Classic 2027Key West, FL · 12 Miles · 4 Miles · from $75 · 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 ↗
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.
- 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
- Apr 25Key West HalfFind 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