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15 running and walking events in Key West, Florida

From big races to Saturday morning group runs—find running and walking 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
  • Healthy Kids Running Series Spring 2026 - Key West, FL [healthykidsrunningseries.org] [Register at runsignup.com]

    Sun, Mar 22, 2026 at 9:00 AM

    Description

    Who We Are: Healthy Kids Running Series is a five (5) week running program in the spring and fall for kids Pre-K through 8th grade. Each HKRS Series takes place once a week and offers age-appropriate...

    Who We Are: Healthy Kids Running Series is a five (5) week running program in the spring and fall for kids Pre-K through 8th grade. Each HKRS Series takes place once a week and offers age-appropriate running events including the 50 & 75 yard dashes, the 1/4 mile, the 1/2 mile and the 1 mile run. Kids will earn points for each race they complete based on their finish.

    Pricing: The registration fee covers the entire five (5) weeks of the Series which includes race bibs for each week, a runner shirt, a finisher medal and any sponsor giveaways. Registration is non-refundable and non-transferable. Online Early Bird registration increases three weeks prior to the first race event.

    Challenger: This Series offers a Challenger Division which is an adaptive 75 yard race for children with disabilities and/or special needs. This allows for parents, siblings, and friends to be on the course with runners to provide support as well as bringing their own supportive devices such as crutches, braces, wheelchairs, etc. to be used by runners.

    Single Day Racing: Single day race registration opens one hour prior to the start of each race. The registration fee covers one single race to be run on the day of registration. ALL single day registrations should be completed onsite at the race location. Single day racers will have the option to upgrade to the full series (see tab on the left side of the page for instructions). There is a strict no-refund and no-transfer policy.

    Awards: All participants receive a medal on Week 5! Trophies will be awarded to the overall top finishers in each of the divisions listed below (broken out by boys and girls respectively):

    Pre-K 50 Yard Dash

    Pre-K 75 Yard Dash

    Kindergarten & 1st Grade

    2nd & 3rd Grade

    4th & 5th Grade

    6th to 8th Grade

    Challenger

    Share your running photos with our community! Find us on Facebook @HealthyKidsRunning or Instagram @healthykidsrs!

    #GetUpandGo

    Kids Run Wheelchair

    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
  • Walk In My Shoes 2026 - Key West [laurenskidswalk.org] [Register at runsignup.com]

    Tue, Mar 31, 2026 at 7:30 AM

    Description

    Join the Lauren’s Kids foundation and thousands of walkers across the state for the 2026 Walk in My Shoes 1,500-mile trek across Florida. April is National Sexual Assault Awareness Month and National...

    Join the Lauren’s Kids foundation and thousands of walkers across the state for the 2026 Walk in My Shoes 1,500-mile trek across Florida. April is National Sexual Assault Awareness Month and National Child Abuse Prevention Month — every step counts in the fight to prevent child sexual abuse and help survivors heal.

    WALK IN MY SHOES KEY WEST

    Date: Tuesday, March 31st, 2026

    Start location: Duval Street Pocket Park (1400 Duval Street, Key West, FL 33040)

    Registration Begins: 7:30 AM

    Walk Start: 8:30 AM

    Details:

    Join us for a 3-mile walk to Publix Super Market at Key Plaza Shopping Center (1112 Key Plaza, Key West, FL 33040)— with the opportunity to stop or continue walking our full 15-mile route to Baby’s Coffee (3180 US-1 MM 15, Key West, FL 33040).

    An UBER code will be provided to walkers to cover the cost of a ride back from the walk.

    15 Miles Walk

    1400 Duval Street, Key West, Florida, 33040, United States
    OpenStreetMap Google Maps

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