Running Races in Key West, Florida — 2026

There are 18 running races in Key West, Florida in 2026. The next is the Fantasy Fest 5K Run/Walk on October 19. Distances include 5K races, half marathons, 10K races.

Fantasy Fest 5K Run/Walk

Mon, Oct 19 · Key West, FL Key West

Virtual Run Like A Rockstar 1 Mile (Untimed)5K Walk5K RUN +1

From $41.99 Open Closing Soon

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Zonta ABC Run/Walk

Sat, Nov 7 · Key West, FL Key West

Road Zonta ABC 5kZonta ABC 10k

From $40 Open

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Key West Half

Sun, Nov 22 · Key West, FL Key West

Road Key West Half - 5KKey West Half - RelayKey West Half - Half Marathon

From $45 Open

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Southernmost Turkey Trot 5K

Thu, Nov 26 · Key West, FL Key West

Virtual Southernmost Turkey Trot 4 & Under (FREE)1 Mile Romp (Untimed)1 Mile Kids' Romp (Untimed) +3

From $0 Open Closing Soon

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Hog Trot 5K

Sat, Nov 28 · Key West, FL Key West

Road 5K Run/Walk5K Run/Walk 12 & Under

From $24.99 Open

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Montessori Key West 5K Run/Walk & Kids Fun Run

Sun, Dec 6 · Key West, FL Key West

Road Montessori Key West Kids Fun Run 0.25 mileMontessori Key West Kids Fun Run 1 mileMontessori Key West 5K Run/Walk

From $20 Open

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Rudolph Red Nose Run

Sat, Dec 12 · Key West, FL Key West

Road A Positive Step 5K Run/Walk

From $50 Open

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Running of the Elves 5K Run/Walk & Jingle Bell Mile

Sat, Dec 19 · Key West, FL Key West

Road JINGLE BELL MILE (Untimed)KIDS JINGLE BELL MILE (Ages 5-12)(Untimed)KIDS 5K (Ages 5-12) +2

From $34.99 Open

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Pole Vault in Paradise 2027

Thu, Jan 7 · Key West, FL Key West

Pole Vault in Paradise 2027

From $75 Open

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2027 Pole Vault in Paradise 5k

Sat, Jan 9 · Key West, FL Key West

Road 5K Run/Walk

From $30 Open

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2nd Annual Save Our First Responders 5K

Sat, Jan 9 · Key West, FL Key West

2nd Annual Save Our First Responders 5K

From $25 Open Closing Soon

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Key West Half Marathon & 5K, 8K, 10K, Rum Stroll & Beer Mile

Sat, Jan 16 · Key West, FL Key West

Virtual Key West Beach N' Beer MileRun Anywhere 5KKey West 5K +11

From $39.95 Open Closing Soon

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Running for Children's Rights to Both Parents - 13 of 50 Half Marathons in 50 States - Florida

Sun, Jan 17 · Key West, FL Key West

Virtual 5K (Virtual)10K (Virtual)1/2 Marathon (In-Person) +1

From $40 Open

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Cupid's Chase 5K Key West

Sat, Feb 13 · Key West, FL Key West

Road 5KPlatinum SponsorGold Sponsor +3

From $40 Open

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Irish Kevin's Shamrock Shuffle 1K/5K/10K 2027

Sat, Mar 13 · Key West, FL Key West

Road 5K Run5K Walk5K - 15 & Under +7

From $20 Open

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KEYS100 Ultramarathon

Sat, May 15 · Key West, FL Key West

Road 50 Mile Individual Ultra50 Kilometer Individual Ultra50 Kilometer Individual Ultra +7

From $230 Open

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Salute to Service presented by The Marker Resort

Sun, May 30 · Key West, FL Key West

Road 5K5k Walk5k Run

From $30 Open

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Hemingway 5K Sunset Run

Sat, Jul 24 · Key West, FL Key West

Virtual 5K Walk (In person event!)5K Run (In person event!)5K Walk (In person event!) +5

From $37 Open Closing Soon

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