Events in Monroe County, Florida | 2026-2027

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
Yeti 12 Days of Vert [ultrasignup.com]
Wed, Dec 31, 2025

Ultra
Monroe County, Florida, United States
OpenStreetMap Google Maps
PKS PTA Family Color Run [runsignup.com]
Sat, Feb 07, 2026 at 8:00 AM

Description

Get ready for the 9th Annual PKS PTA Family Color Run on Saturday, February 7, 2026—a super fun, family-friendly run/walk where everyone starts bright and finishes covered in color! 💥🌈

Participants...

Get ready for the 9th Annual PKS PTA Family Color Run on Saturday, February 7, 2026—a super fun, family-friendly run/walk where everyone starts bright and finishes covered in color! 💥🌈

Participants can run, jog, dance, or stroll the course at their own pace as volunteers sprinkle bursts of colorful powder along the way. This is all about laughs, community spirit, and making messy memories together—perfect for kids, grown-ups, and grandparents too.

Wear white or light colors, bring your biggest smile, and join us for a high-energy day supporting PKS PTA programs and enrichment for our school. All ages welcome!

3.1 Miles Run
Monroe County, Florida, 33070, United States
OpenStreetMap Google Maps
USA Women's Half Marathon Florida Keys [usawomensracefl.com] [Register at runsignup.com]
Sat, Feb 14, 2026 at 7:00 AM

Description

All finishers receive a luxury custom sterling silver signature pendant and necklace, Bamboo Brook race shirt, all professional race photos, a custom tote bag, mimosas, and continental breakfast food at the finish. The 13.1 race course is a sanctioned USATF-certified course.

13.1 Miles Half Marathon Run
77522 Overseas Hwy, 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
Sombrero Beach Run [sombrerobeachrun.org] [Register at runsignup.com]
Sat, Feb 28, 2026 at 8:00 AM

Description

The Key West Southernmost Runners Club welcomes you to the 18th Annual Sombrero Beach Run. This is the #1 Running Event of its' kind in the Florida Keys! If you are looking for a truly special...

The Key West Southernmost Runners Club welcomes you to the 18th Annual Sombrero Beach Run. This is the #1 Running Event of its' kind in the Florida Keys! If you are looking for a truly special run/walk for your vacation in paradise, this race has it all. Kick off Friday night with a registration party at Sombrero Beach, Marathon, FL. Race day, be swept away with entertainment by a DJ , runners breakfast, after race lunch, drinks, ice cold beer, custom t-shirts, raffles, all at the spectacular setting of Sombrero Beach. Stay for the weekend and on Sunday we are adding additional fun events.

3.1 Miles 6.2 Miles 9.3 Miles Run Walk
Monroe County, Florida, 33050, 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

45th Annual 7-Mile Bridge Run [runsignup.com]
Sat, Apr 11, 2026 at 6:45 AM

Description

IMPORTANT: PLEASE READ THE INFORMATION BELOW BEFORE YOU SUBMIT YOUR APPLICATION TO AVOID DISAPPOINTMENT LATER!

You MUST show your Photo ID WITH THE SAME ADDRESS YOU REGISTERED WITH when picking up...

IMPORTANT: PLEASE READ THE INFORMATION BELOW BEFORE YOU SUBMIT YOUR APPLICATION TO AVOID DISAPPOINTMENT LATER!

You MUST show your Photo ID WITH THE SAME ADDRESS YOU REGISTERED WITH when picking up your number.

NO EXCEPTION/NO REFUNDS

The date for the 45th Annual 7 Mile Bridge Run will be on April 11th, 2026. Registration is ONLINE ONLY.

On January 27th, 2026 registration opens for everyone. Anyone can register on this date, but we are only able to accept 1500 entries and the field fills very quickly. You must show a PHOTO ID when picking up your bib number that matches the same address you used to register.

PACKET PICKUP IS ON FRIDAY, APRIL 10, 2026 BETWEEN NOON AND 8:00 PM ONLY. MAKE PLANS NOW TO BE ABLE TO BE THERE. YOU MUST BE PRESENT TO PICKUP YOUR NUMBER! NO EXCEPTIONS!

Each individual participant must pick up their own race packet with a valid Photo ID.

We will not accept digital copies, photocopies, screenshots of IDs, and/or photos of

IDs on your phone. These WILL NOT be accepted, you will NOT receive your packet,

and entry will be denied. Parents/Guardians with their ID’s may pick up packets for

their minor children. No bib number transfers, or family/friend pick-ups allowed. NO

EXCEPTIONS! NO REFUNDS!

We use Runsignup.com for registration, so prior to registration you should create an account which will help to expedite your registration.

7 Mile Bridge Run Race Committee

REMEMBER, YOUR PHOTO ID MUST MATCH THE ADDRESS YOU SIGN UP WITH!

MONROE COUNTY RESIDENTS:

You must be a full time resident with your photo ID (license) matching the address you signup with. No exceptions.

7 Miles Run
1 Knights Key Blvd, Monroe County, Florida, 33050, United States
OpenStreetMap Google Maps
Pascal's Way 5K [runsignup.com]
Sat, May 02, 2026 at 8:30 AM

Description

Description:

The 5th Annual Pascal’s Way 5K Run/ Walk can be participated in locally, in Islamorada, FL or virtually whenever and wherever is convenient up until the end of May. The in-person event...

Description:

The 5th Annual Pascal’s Way 5K Run/ Walk can be participated in locally, in Islamorada, FL or virtually whenever and wherever is convenient up until the end of May. The in-person event will take place at 8:30 AM on Saturday May 12, 2026, at the Treasure Village Montessori campus in Islamorada. FL.

This 5K run/walk honors the life of Pascal Weisberger who passed away 6 years ago, and this year is supporting the Pascal’s Way Scholarship for community service-oriented seniors from the Class of 2026 at Coral Shores High School (CSHS). Any additional funds will go to support the science programs of Treasure Village Montessori (TVM) in Islamorada and Ocean Studies Charter School (OSCS) in Key Largo. Over the course of his 9 years living in the Upper Keys, Pascal attended both of these amazing schools and they each added greatly to his life and him becoming the special young man that he was known to be in his community.

Pascal’s Way is about being a good human, and Pascal’s example in his short 14 years has moved the entire community in the FL Keys to set aside a day of good will and community service, the Annual Pascal Weisberger Day of Service on February 2nd each year. We hope that spirit shines and enriches the experience for everyone who participates in this annual 5K run/walk, an activity that played a significant role in Pascal's life and development.

Anyone interested in participating can walk or run a ~5K distance at the location of their choice on Saturday, May 2nd at 8:30 AM, or at any other time that is convenient during the month. In lieu of a formal registration fee we ask that you make a donation on this registration site in the suggested amount of $30-40, though we encourage your participation even if you can only afford a smaller amount. Amounts above the suggested donation are also welcome and encouraged, as well as from folks who don't plan to run or walk, but would like to support CSHS Class of 2026 graduating seniors, and the science programs of local schools.

The in-person race on May 2nd will follow the Old Highway/State Road 4A in Islamorada, starting and ending by the entrance to Treasure Village Montessori, with the turn-around being at the Old Highway entrance to Forest Tek Lumber.

Thank you for signing up to participate in honor of Pascal Weisberger, he would be humbled by your continued remembrance, and appreciative of those willing to support young people who recognize the importance of service to others, as he always did. #PascalsWay

A Pascal's Way race t-shirt, magnet, and wristband will be provided to each participant and post-race refreshments will be available, as well as a raffle and slideshow about Pascal's life.

Additional Information:

Phone: (305) 879-2118

Email: apoholek@gmail.com

Website: https://www.facebook.com/PascalsWay.org

5k Run Virtual Walk
77522 Overseas Hwy, Monroe County, Florida, 33036, United States
OpenStreetMap Google Maps
Swim for Alligator Lighthouse [swimalligatorlight.com] [Register at runsignup.com]
Sat, Sep 12, 2026 at 7:45 AM

Description

“The 8-mile swim to Alligator Lighthouse is a challenge. It’s not for the faint of heart"

How it started

When World Renowned Artist, Lighthouse Larry decided to swim, in his native town of...

“The 8-mile swim to Alligator Lighthouse is a challenge. It’s not for the faint of heart"

How it started

When World Renowned Artist, Lighthouse Larry decided to swim, in his native town of Islamorada, to Alligator Lighthouse and back, alone and self-supported, his friends thought he was crazy. When he then said out loud “every open water swimmer should experience this,” Larry became the anchor to the Swim for Alligator Lighthouse.

The Fighting Manatee Swim Club, the Masters swim club of Islamorada, accepted the challenge to present a world class open water swim event in the Florida Keys to help raise awareness and funds to Save Alligator Lighthouse. The Fighting Manatees presented the Inaugural Swim for Alligator Lighthouse in 2013. It’s here to stay!

Race Overview

The Swim for Alligator Lighthouse is an 8-mile open water swim. Participants swim 4 miles, circle Alligator Lighthouse, and swim 4 miles back. The event is open to solo swimmers, 2 person, 3 person and 4 person teams. Every solo or relay team requires a support kayak. Solo swimmers will need to enlist a kayaker to accompany them the entire race, while relay groups will alternate kayaking with swimming.

Full Event Details can be found at https://www.swimalligatorlight.com/

8 Miles Open Water Swim
77522 Overseas Hwy, Monroe County, Florida, 33036, United States
OpenStreetMap Google Maps
Old Highway 5k Run/Walk [runsignup.com]
Sat, Oct 03, 2026 at 7:30 AM

Description

Challenge your best time in the Annual Old Highway Run/Walk. Run or walk our legendary highway. It is the legendary Old Highway in Islamorada. It's an awesome flat course with lots of shade.

The race...

Challenge your best time in the Annual Old Highway Run/Walk. Run or walk our legendary highway. It is the legendary Old Highway in Islamorada. It's an awesome flat course with lots of shade.

The race is a timed 5K Run/Walk that starts and finishes at Coral Shores High School, which will be the benefiting partner with 50% of the proceeds going to the school.

Race shirts and participant medals will be available to the first 200 participants to register.

Awards will be presented to the Overall Top Three Finishers Male & Female, Overall Masters Male & Female, as well as, to the Top Three Male & Female for the following age groups:

5k Awards

<9

10-13

14-15

16-19

20-24

25-29

30-34

35-39

40-44

45-49

50-54

55-59

60-64

65-69

70-74

75-79

80+

After your race, you can reunite with family and friends while enjoying snacks, refreshments, and music.

Please note disclaimer:

Race management reserves the right to postpone or cancel the event due to events outside of managements control such as natural disaster and/or other emergencies. No Refunds will be issued under these circumstances. Management may also alter the course and distances for the safety of athletes.

Entry is Non-Refundable, Non-Deferable, and Non-Transferable.

NO Pets, Skateboards, Rollerblades will be permitted on the course.

All times and locations are subject to change.

5k Run Walk
89901 Old Highway, Monroe County, Florida, 33070, United States
OpenStreetMap Google Maps
Old Highway 5K [finishers.com] - Facebook
Sat, Nov 14, 2026

5k Run
Monroe County, Florida, United States
OpenStreetMap Google Maps
Islamorada Half Marathon [finishers.com]
Sat, Dec 12, 2026

5k 10k Half Marathon Run
Monroe County, Florida, United States
OpenStreetMap Google Maps
Islamorada Half Marathon & 10k, Rumrunner Run 5K/10K and Beach N' Beer Mile [islamoradarunning.com] [Register at runsignup.com]
Sat, Dec 12, 2026 at 8:00 AM

Description

Welcome to the 12th annual Islamorada Half Marathon & 10K, Rumrunner Run 5K and Beach N’ Beer Mile! Our full weekend of road races and parties has become a bucket list event for people from all over the world. As the largest event in the upper Keys, we love bringing all our runners down to our little island to enjoy everything Islamorada has to offer.

1 Miles 5k 6.2 Miles 10k 13.1 Miles Half Marathon Run
77522 Overseas Hwy, Monroe County, Florida, 33036, United States
OpenStreetMap Google Maps
USA Women's Half Marathon Islamorada, Florida Keys [usawomensracefl.com] [Register at runsignup.com]
Sat, Feb 06, 2027 at 7:00 AM

Description

All Finishers receive a Luxury Custom Sterling Silver Signature Pendant and Necklace, Custom Race Shirt, all Professional Race Photos, a Custom Tote Bag, Mimosas, and Continental Breakfast Food at the finish.

13.1 Miles Half Marathon Run
77522 Overseas Hwy, Monroe County, Florida, 33036, United States
OpenStreetMap Google Maps
USA Women's Half Marathon Florida Keys [finishers.com]
Sat, Feb 13, 2027

Half Marathon Run
Monroe County, Florida, United States
OpenStreetMap Google Maps

17 events in Monroe County, Florida

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