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10 events in Key West, Florida

From big races to Saturday morning group runs—find 5k events and connect with the local endurance sports community.

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  • Cupid's Chase 5K Key West [runsignup.com]

    Sat, Feb 14, 2026 at 9:00 AM

    Description

    • Check-in begins at 7:30 AM and the race starts at 9:00 AM.

    • The event is fully accessible and pet-friendly, but all pets must remain leashed at all times.

    • This is a certified 5K with...

    • Check-in begins at 7:30 AM and the race starts at 9:00 AM.

    • The event is fully accessible and pet-friendly, but all pets must remain leashed at all times.

    • This is a certified 5K with professional timing. All results will be posted immediately after the race.

    • To guarantee your Cupid's Chase shirt, please register by January 1, 2026; after that date, shirts will be available while supplies last.

    • Giveaways include a Cupid's Chase finisher medal and drawstring bag, available while supplies last.

    • Trophies will be awarded to the top 3 overall male and female finishers.

    • Age group medals will be awarded to the overall male and female finishers in each of the following 14 age groups: 12 & under, 13–15, 16–19, 20–24, 25–29, 30–34, 35–39, 40–44, 45–49, 50–54, 55–59, 60–64, 65–69 and 70 & over.

    • This is a rain or shine event. All registration fees are non-refundable.

    3.1 Miles 5k Run

    Key West, Florida, 33040, United States
    OpenStreetMap Google Maps
  • Irish Kevin's Shamrock Shuffle 5K/10K 2026 [runsignup.com]

    Sat, Mar 14, 2026 at 8:00 AM

    Description

    Run or walk your way St. Paddy's style through Key West for our 13th Annual IK Shamrock Shuffle. Starting & finish at Irish Kevins on Duval Street, followed by THE BEST Post-Race Party in Key West....

    Run or walk your way St. Paddy's style through Key West for our 13th Annual IK Shamrock Shuffle. Starting & finish at Irish Kevins on Duval Street, followed by THE BEST Post-Race Party in Key West. Featuring live entertainment, One Free Alcoholic Beverage (21+) or non-alcoholic drink, a complimentary breakfast buffet, T-Shirt, SWAG BAG for all participants, and awards ceremony. 100% of the money goes directly to the featured charities.

    WE WILL BE COLLECTING NON-PERISHABLE FOOD DONATIONS FOR THE BAHAMA VILLAGE LITTLE PANTRY DURING PACKET PICK UP THE DAY BEFORE THE RACE, AND THE DAY OF THE RACE.

    Join us as we 'Celebrate St. Paddy's, Key West Style'!

    5k 10k Run Walk

    1400 Duval Street, Key West, Florida, 33040, United States
    OpenStreetMap Google Maps
  • Southernmost Seminoles 5K Renegade Run/Walk [southernmostrunners.com] [Register at runsignup.com]

    Sat, Mar 28, 2026 at 8:00 AM

    Description

    Benefiting: Local Scholarships

    Course: The 5K will start at Truman Waterfront with three loops.

    Pre-registration and Packet Pickup Mar 27th, 5:00 - 7:00 pm @ Island Dogs Bar 505 Front Street

    Race Day...

    Benefiting: Local Scholarships

    Course: The 5K will start at Truman Waterfront with three loops.

    Pre-registration and Packet Pickup Mar 27th, 5:00 - 7:00 pm @ Island Dogs Bar 505 Front Street

    Race Day registration and Packet Pickup @ Truman Waterfront 7:00 -7:45 am

    Medals Awarded to:

    Overall M & F Winners,

    Masters M & F Winners, Top 2 M & F in each 10 year age

    group for 5K runners including youth along with Top 2

    M & F walkers

    SPECIAL AWARD TO THE MOST SPIRITED SEMINOLE

    T-shirts will be given to the first 100 registrants.

    Celebrate after the race with beverages, free snacks

    and lots of door prizes and drawings

    3.1 Miles 5k Run Walk

    Key West, Florida, 33040, United States
    OpenStreetMap Google Maps

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