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9 events in Monroe County, Florida

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

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  • Islamorada Half Marathon & 10k, Rumrunner Run 5K/10K and Beach N' Beer Mile [islamoradarunning.com]

    Sat, Dec 13, 2025

    1 Mile 5k 10k Half Marathon Run

    81801 Overseas Highway, Monroe County, Florida, 33036, United States
    OpenStreetMap Google Maps
  • Run With Deer 5K Run/Walk [southernmostrunners.com] [Register at runsignup.com]

    Sat, Feb 14, 2026 at 8:00 AM

    Description

    10th Annual Run With Deer 5K Run/Walk - Saturday, February 14, 2026, Big Pine Key 8:00 am

    Run Location: Big Pine Community Park, 31009 Atlantis Dr, Big Pine, FL 33043

    Pre-Registration & Packet Pickup...

    10th Annual Run With Deer 5K Run/Walk - Saturday, February 14, 2026, Big Pine Key 8:00 am

    Run Location: Big Pine Community Park, 31009 Atlantis Dr, Big Pine, FL 33043

    Pre-Registration & Packet Pickup Friday, February 13th 5-7pm - Big Pine Community Park

    RACE DAY Registration & Packet Pickup Saturday, February 14th 7:00 am to 7:45 am - Big Pine Community Park

    Register before January 21, 2026 for early bird registration prices.

    Age Group Awards!

    5K Run: Top Overall Male and Female; Top Masters Male and Female; Top 2 each 10 year age group

    5K Walk: Top 3 Overall Male and Female

    Proceeds benefit The Florida Keys Wildlife Society - The Florida Keys Wildlife Society helps the Florida Keys National Wildlife Refuges carry out their mission to protect the habitat and wildlife of the Florida Keys. Florida Keys Wildlife Society (Formerly FAVOR) - the official Friends Group for the Florida Keys National Wildlife Refuges. supports activities that include nature programs for kids, families and adults, education and outreach events, wildlife festivals, research projects, native tree planting, trash cleanups, photography club activities, volunteer programs and much more. Join Us! www.floridakeyswildlifesociety.org Click the Donate button above to make and additional donation to Florida Keys Wildlife Society

    3.1 Miles 5k Run Walk

    Monroe County, Florida, 33043, United States
    OpenStreetMap Google Maps
  • St Patty’s Island Run 5K/10K [runsignup.com]

    Sun, Mar 15, 2026 at 8:00 AM

    Description

    The Islamorada Running Company is proud to announce our first annual St. Patty's Island Run at the Florida Keys Brewing Company!

    5k 10k Run

    81611 Old Hwy, Monroe County, Florida, 33036, United States
    OpenStreetMap Google Maps
  • SUGARLOAF SCHOOL PTO FINS UP 5K RUN/WALK & 1M KIDS FUN RUN [runsignup.com] [Register at runsignup.com]

    Sat, Mar 28, 2026 at 8:00 AM

    Description

    EVENT INFORMATION:

    Please join us for the 4th Annual FINS UP 5K RUN/WALK & 1 MILE KIDS FUN RUN on Sat, Mar 28, 2026. Both events are proudly brought to you by the Sugarloaf School Parent Teacher...

    EVENT INFORMATION:

    Please join us for the 4th Annual FINS UP 5K RUN/WALK & 1 MILE KIDS FUN RUN on Sat, Mar 28, 2026. Both events are proudly brought to you by the Sugarloaf School Parent Teacher Organization.

    Come be a part of a great race for a great cause! All proceeds raised go directly to support the amazing students and staff at Sugarloaf School through the Sugarloaf School PTO, a 501C3 Organization.

    This family friendly race is open to all ages and abilities! Everyone is welcome and encouraged to participate! The race will begin and end at the Sugarloaf School Shark Park at the corner of Crane Blvd and US1. Plenty of parking is available in the school parking lots and in the grass areas along Crane Blvd (please do not park on the bike path).

    If running or walking is not your thing, please feel free to volunteer (we need lots of help) or just come out and cheer for our participants.

    A HUGE THANK YOU GOES OUT TO OUR GENEROUS SPONSORS FOR THIS EVENT!!!!

    GOLD SPONSORS:

    TERRY KELLY

    REEL MEMORIES BOAT RENTALS

    SUGARLOAF CHURCH

    SEACAMP

    SILVER SPONSORS:

    REGISTRATION:

    5K Run/Walk Registration Fees are as follows:

    January Early Registration - $20 for adults and $15 for youth (17 & under)

    February Early Registration - $27 for adults and $20 for youth (17 & under)

    March Regular Registration - $35 for adults and $25 for youth (17 & under)

    1M Kids Fun Run Registration Fees are as follows:

    January Early Registration - $13 for children 11 & under only

    February Early Registration - $15 for children 11 & under only

    March Regular Registration - $18 for children 11 & under only

    Paper entry forms are available by contacting the race coordinator below.

    BIB/PACKET PICK UP AND LATE REGISTRATION:

    Bib and packet pick-up will be available on Fri, Mar 27 from 2:30 - 5:00 pm at the Sugarloaf School Pick Up Circle. Late in person registration will also be available.

    Bib and packet pick-up will be available on race day morning on Sat, Mar 28 from 6:30 - 7:30 am.

    COURSE:

    The 1M Kids Fun Run starts promptly at 8:00 am. The course will be 2 laps of the Sugarloaf School Shark Park Track.

    The 5K Run/Walk starts at 8:30 am. The course begins at the Sugarloaf School Shark Park Track, proceeds north on Crane Blvd all the way to the National Key Deer Preserve Barrier where it will loop around and return to the Sugarloaf School Track. One aid station with water and electrolytes will be located at the turn around. Cones, signs and volunteers will clearly guide the runners and walkers on the route.

    GIVEAWAYS:

    5K Run/Walk and 1M Kids Fun Run participants will receive T-SHIRTS and Sponsor Giveaways.

    ALL PARTICIPANTS WILL RECEIVE A T-SHIRT!!! Size is not guaranteed for registrations received after March 13

    AWARDS:

    The 1M Kids Fun Run is not a timed event. Overall Awards will be given to Top 3 Boys and Top 3 Girls. All finishers will receive a Finishers Medal.

    The 5K RUN is a timed event. Overall Awards will be given to the Top 3 Males and Top 3 Females, Top Male Master (40+) and Top Female Master (40+), as well as Age Group Awards for Males and Females 3 Deep in the following categories: 0-10, 11-19, 20-29, 30-39, 40-49, 50-59, and 60+.

    The 5K WALK is a timed event. Overall Awards will be given to the Top 3 Males and Top 3 Females.

    RULES & REGULATIONS:

    1. Participants must wear their official race number on the FRONT. It must be visible at all times.

    2. Knowing the course is the responsibility of the runner. The course will be clearly marked with cones, signs and volunteers.

    3. No unregistered runners, walkers, or pacers.

    4. No pets, bicycles, skates, scooters, or skateboards.

    5. Strollers/baby joggers are allowed but should be users should be aware that there are gravel areas and very narrow sections on the course.

    6. No unregistered runners, walkers, or pacers.

    7. Slower runners and walkers should stay right and allow faster racers to pass on the left. Faster runners and walkers should inform participants when they are approaching and passing on the left. Racers that have turned and are approaching the finish line have the right of way. Please always give way to the faster participants.

    8. Absolutely NO LITTERING on the course.

    3.1 Miles 5k Fun Run Gravel Kids Run Walk

    Monroe County, Florida, 33042, United States
    OpenStreetMap Google Maps
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