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Showing 20 of 20 races found
NOV 7

Zonta ABC Run/Walk

Key West, FL
Join us for the 34th Annual Zonta ABC 5K and 10K Run/Walk ABC stands for “Awareness Breast Cancer” The Zonta Club of Key West encourages you to join in with the other runners and walkers for this year’s event starting at 7:30am for the 10K and 8am for the 5K on Saturday, November 7, 2026.  Packet pickup and registration will be held east of Salute @ Higgs Beach on Friday, November 6th from 5:00pm-7:00pm and on race day Saturday, November 7th from 7:00 am-7:45 am. The money raised from this event goes to providing important preventive services for women who otherwise cannot afford them. This annual event has changed the lives of many women in the lower keys. Zonta has been able to provide over 3,500 mammograms to local women over the past 33 years and have never turned any woman in need away. Packet goodies include free koozies, tshirts, and don't forget that coveted Puzzle Piece Finishing medal! Stay for the after party and awards as this will be a fun filled event while raisin
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NOV 22

Key West Half

Key West, FL
Most finish lines give you a medal. This one gives you a story. It starts in Key West, where the ocean frames the course, the island wakes up around you, and the road ahead feels like an invitation. Choose the Half Marathon, the 5K, or share the miles with a teammate in the Half Marathon Relay. Run for a personal best. Run to prove something to yourself. Or run simply because some experiences are worth saying yes to. On November 22, 2026, you will arrive as a runner. You will leave with a story only Key West could give you. Race the Keys.
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NOV 26

Southernmost Turkey Trot 5K

Key West, FL
Gather your flock and join us for the 3rd Annual Southernmost Turkey Trot 5k & 1 Mile Rooster Romp Benefitting Reef Relief.  Start Times on Thanksgiving Morning: 5K @ 8:00 am 1 Mile Rooster Romp @ 8:10 am Start & Finish at the Southernmost Buoy Not Ready for a 5K, No Problem! Register for the untimed 1 Mile Rooster Romp Walk Want more this Thanksgiving, take the Double Trot Challenge!   All Participants Receive:  Free Super Soft Adult Race T-Shirt Free Cotton Youth Race T-Shirt Free Festive Finisher Medal Free Mimosa at our Mimosa Bar (21+ Only) Picture with our Mascot Dash at the Southernmost Point Buoy Military Families welcome, use for HERO for 10% off. Present ID at Packet Pick Up
5K
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NOV 28

Hog Trot 5K

Key West, FL
50 YEAR ANNIVERSARY OF HOG'S BREATH SALOON.32nd YEAR OF THE HOG TROT 5K!   START WITH A RUN. END WITH A BEER. ARE YOU READY? Celebrate two legendary Key West traditions as the 50th Anniversary of Hog's Breath Saloon meets the 32nd Annual Hog Trot 5K! Run, walk, or jog through beautiful Key West before crossing the finish line for an unforgettable post-race celebration at the world-famous Hog's Breath Saloon. Each participant will receive a FREE T-SHIRT and ONE FREE MICH ULTRA!  Keep the party rolling with the Post-Race Party drink until 11 AM:Grey Goose Bloody Mary's - $8High Noons - $5  Our 2026 Charity Partner for the Hog Trot is Autism Society of the Keys.
5K
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DEC 6

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

Key West, FL
Caring for our bodies is as important as caring for our minds. Join us the morning of Sunday, December 6th as we throw a celebration of fitness and community and raise crucial funding for our dreamy little island school. This race offers something for everyone: Run the 5K race, walk the 5K race, kids can run the 1 mile race or the 0.25 mile race - all in a safe and easy location for the whole family at Truman Waterfront Park. Kids can play on the playground while the grown ups get their fitness, and grown ups can cheer for their kids using their bodies and having fun with their friends in the kids races. The event begins at the promenade at the USCGC Ingham Maritime Museum at Truman Waterfront Park. Award medals given for the top finishers in the 5K and 1mile races! Pre-Registration & Packet Pickup Friday, December 4th from 2:45pm - 4:45pm at the Montessori School, 1221 Varela St. Race day check-in starts at 7:00am with 8:00am start time for the 5k. Kids' Run check-in is from 7:00am - 8:45am. After the race, enjoy refreshments, an award ceremony, and a dance party. Finisher medals given to all participants and t-shirts for the first 100 who register. RACE START TIMES 8:00 am 5k race 9:00 am Kids' Run (1mile and 0.5 mile) Runners and walkers of all ages and abilities are welcome to participate. Proceeds benefit the Montessori Children's School of Key West, a non-profit, parent-based corporation serving children ages 18 months through 10th grade. Donations are tax deductible. All participants, volunteers, and attendees are invited to celebrate with us following the Kids Fun Run at our first ever Finish Line FOAM Party! Smart to bring a towel and change of clothes if you plan to play in the foam. Foam is eco-friendly and safe, hypoallergenic (made of coconut oil & coconut husk.) Volunteer Here!!
5K
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DEC 12

Rudolph Red Nose Run

Key West, FL
Don your festive holiday jammies and join in the 18th annual A Positive Step 5K, taking place Saturday morning, December 12th, 2026.  The race will start and end at the Southernmost Beach Café,1405 Duval Street, Key West.  Race day check-in starts at 7:00am with 8:00am race start time. After the race, enjoy refreshments, prizes, and a fabulous silent auction.  🏃‍♀️🏃‍♂️Register today and don't miss out! Every registered runner will receive:🎒A collectible race bag🥤A commemorative race cup👕An official event T-shirt 🏅Winners in each age category will also take home one of our popular laser-engraved wooden medals—a unique race tradition that participants look forward to every year!  There will also be prizes for most festive and unusual PJ’s.  🤶🎅 💲Register now for just $50!📆Registration increases to $60 in December, so sign up early and save! Pre-race packet pickup is Friday, Dec. 11th from 5:00-7:00pm at th
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DEC 19

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

Key West, FL
Are you ready to get your Elf on this holiday season! Ready to get in the Holiday Spirit? Grab your festive holiday costumes and Run, Jog, Stroll or Jingle all the Way to the finish line and celebrate at our Post-Race Christmas Party at Kaya Island Eats. Make this event your new favorite tradition with charity partner Reef Relief and help bring together the community in a whimsical display of Elf cheer. Not Ready for a 5K. No Problem. Check out the Jingle Bell Mile. The Jingle Bell Mile is an untimed walk/stroll for those who aren't ready for a 5K. Come spread holiday cheer in your favorite holiday costumes, Christmas lights and be part of this holiday event. No South Pole Elves Welcome Here! Santa will be watching! Saturday, December 19th- Kaya Island Eats 5K @ 8:00 AM Jingle Bell Mile @ 8:05 AM 4 and under free Register TODAY! Don't be a Cotton Headed Ninny Muggin! Military Families Welcome. Use Code HERO for 10% off. Present ID at Packet Pick Up.
5K
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JAN 7

Pole Vault in Paradise 2026

Key West, FL
January 1 - 3, 2026!  Pole Vault Clinic - Friday, January 2, 10 AM to Noon Competition Day - January 3, 2026 On January 5, 2019, the First Annual Pole Vault in Paradise brought together pole vaulters from age 9 to 75 to compete alongside some of the best pole vaulting elites from around the country. What better place is there to vault than Key West in January?  We were the first outdoor meet of the season and raised significant funds for the Key West High School Track Team.   Pole Rental is available via The Pole Drop 321-266-8916 www.Skypolevaulter.com Join us as we return for our 8th event on Higgs Beach in beautiful Key West!
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JAN 7

Pole Vault in Paradise 2027

Key West, FL
January 7 - 10 2027 Pole Vault Clinic - Friday, January 8, 10 AM to Noon Competition Day - January 9, 2026 On January 5, 2019, the First Annual Pole Vault in Paradise brought together pole vaulters from age 9 to 75 to compete alongside some of the best pole vaulting elites from around the country. What better place is there to vault than Key West in January? We were the first outdoor meet of the season and raised significant funds for the Key West High School Track Team. Pole Rental is available via The Pole Drop 321-266-8916 www.Skypolevaulter.com Join us as we return for our 9th event on January 9, 2027 at Higgs Beach in beautiful Key West!
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JAN 9

2nd Annual Save Our First Responders 5K

Key West, FL
ON YOUR MARK, GET SET, GO!!! THE 2ND ANNUAL SAVE OUR FIRST RESPONDERS 5K Lace up for our heroes! Join us as we continue our mission during Monroe County’s annual First Responders Week. This event is a prayerful dedication to raising vital awareness and support for the mental health challenges and job-related trauma faced by those who run toward danger to keep us safe. EVENT DETAILS: DATE: Saturday, January 9, 2027 TIME: 8:00 AM – 10:00 AM LOCATION: Truman Waterfront Park (Near the Coast Guard Cutter Ingham), Key West, FL 33040WEBSITE & REGISTRATION: https://saveourfirstresponders.org THE COURSE & COMPETITION SCENIC RUN/WALK: Participants will complete three scenic laps around the park, offering views of the historic Coast Guard Cutter Ingham. THIS EVENT IS OPEN TO THE PUBLIC OF ALL AGES AND ABILITIES. THE "SUPER EIGHT" CHALLENGE:  Eight separate teams compete, honoring the service of: 911 Dispatchers; Correctional Officers; Correctional Probation Officers; Crime Scene I
5K
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JAN 9

2027 Pole Vault in Paradise 5k

Key West, FL
Event OverviewThe Pole Vault in Paradise 5K is a fun run with no chip timing, designed to be scenic, welcoming and celebratory. All proceeds directly support local youth athletics and help grow future track and field athletes in our community. Course DetailsThe run will start at Higgs Beach, head down the path toward Smathers Beach (with iconic ocean views), and finish on the White Street Pier.  Packet PickupFriday 3:00–5:00 PM at Higgs BeachSaturday: 6:45–7:45 AM at Higgs BeachParticipants who registered by December 15 will receive an event shirt at packet pickup.  Parking Information (Important)Please note that parking directly at Higgs Beach will be limited and partially blocked due to event setup and operations near Salute. We recommend: Parking in public parking lotsParking at the park across the street Allowing extra time to walk to the start area After the Run We encourage you to stick around and enjoy the day: Watch local and elite athletes compete in Pole Vault in ParadiseBid
5K
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JAN 16

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

Key West, FL
KEY WEST HALF MARATHON VOTED ONE OF THE 10 BEST HALF-MARATHONS ACROSS THE NATION FOR 2023 IN USA TODAY!!! CLICK HERE TO LEARN MORE!   Welcome to our 29th Year!   The 29th Annual Key West Half Marathon and Runfest is on January 16th & 17th, 2027!  LET'S PARTY!!  All Participants receive a race shirt, finisher medal, race bag, food and drinks, rum tasting, Race party and great entertainment! All races are available as virtual options!
5K10KHalf Marathon
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JAN 17

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

Key West, FL
This is a virtual race open to supporters across the country who want to take action for children and families. Participants can run, walk, or move in their own community while supporting a national mission to protect children’s relationships with both parents. This race is part of a larger effort to run 50 half marathons in 50 states, completing one race each month. Each run is dedicated to raising awareness about parental alienation, family court practices that separate children from a loving parent, and the urgent need for children to have reasonable access to both parents. Parental alienation and unnecessary parent-child separation cause long-term emotional, psychological, and developmental harm. This run exists to bring visibility to that harm and to advocate for fair, child-focused family court outcomes. This event is Run 13 of 50. The founder of Mothers and Fathers Truly Matter, Bob, will be running this race in Florida while supporters participate virtually from anywhere.  All
Half Marathon
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FEB 13

Cupid's Chase 5K Key West

Key West, FL
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, 2027; 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.
5K
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MAR 13

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

Key West, FL
RUN. WALK. SHUFFLE. CELEBARTE!   Get ready to celebrate St. Paddy's at the 14th annual Irish Kevin's Shamrock Shuffle! Run, walk, or shuffle your way through Key West, then head back to Irish Kevin's on Duval Street for the BEST post-race party in town!   -Complimentary breakfast buffet -One FREE alcoholic beverage (21+) or non-alcoholic drink -Official race t-shirt -Swag Bag  -Race medal for every participant -Awards ceremony   Best of all, 100% of ALL of the money raised goes directly to our featured charities (those will be announced shortly) HELP US STOCK THE LITTLE PANTRY We'll also be collecting non-perishable food donations for the Bahama Village Little Pantry during packet pickup and on race day! So grab your green, bring your friends, and get ready!
5K10K
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MAY 8

Key West Paddle Classic 2027

Key West, FL
Welcome to the 30th Annual Key West Paddle Classic!   As a Favorite Destination Race, we offer one of the largest paddle categories on the East Coast! The Key West Paddle Classic is officially ON for May 8th, 2027! We’re excited to announce our new partnership with: Beachside Resort & Residences + Blue Flamingo Hotel The event will be hosted start and finish right here at Beachside and official after parties at Blue Flamingo Hotel! New location, same awesome race. This one’s going to be epic.  Join Florida Keys Watermans Company as we celebrate taking over as hosts of the Key West Paddle Classic!  The event has a long history, originating in 1997 under the direction of Micheal O'Shaunessy, and is celebrating its 29th year in 2026! Lazy Dogs hosted the event from 2013-2024 and graciously passed the torch to us for this year!    If you have been a regular and racing the event for years, we thank you for coming back!  If it is on your race ‘bucket’ list, well my friends, THIS
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MAY 15

KEYS100 Ultramarathon

Key West, FL
Registration is open for the 18th Annual race across the islands of the Florida Keys--May 16-17, 2026.  This chain of unique and inter-connected islands--some inhabited, some not--end in the City of Key West, just 90 miles from Cuba. This is a pavement race, with approximately 75% run on paved bike paths or sidewalks and the balance on the road shoulder facing traffic.  The Florida Keys, known locally as "The Conch Republic", is a spectacular and laid-back sub-tropical paradise, surrounded by the turquoise waters of the Atlantic Ocean and Florida Bay/Gulf of Mexico. The Keys feature great fishing, kayaking, snorkeling and diving, hotels, resorts, B&B's and cuisine and cocktails to fit every budget. There is entertainment to fit every taste, important history and a unique culture, sunsets that will keep you spellbound, special events going on throughout the year including KEYS100, of course, and you don't need a passport to visit here! So, what are you waiting for? W
Marathonultra
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MAY 30

Salute to Service presented by The Marker Resort

Key West, FL
Join us over Memorial Day weekend to honor those who serve. The second annual Salute to Service will take place on Sunday, May 24, 2026 and finish with a Pool Party @ The Marker. A portion of proceeds from the event will be donated to the Key West Firefighter's Hardship Fund.  Saturday May 23 @ 200 William Street Happy Hour Pool Party Packet Pick Up 4-6pm Sunday May 24 @ 200 William Street Pre race packet pick up 7:30-8:30am8:30am Color Presentation/National Anthem/Race startPost Race snacks and awards at The Marker
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JUN 1

Way Gay 5K

Key West, FL
We're coming back for another year! Way Gay 5K! Your time to shine! Are you the most fantastic? Best finish line prancer? Glitteriest and Grittiest? Show us you skills- walk, run, dance, prance, wear fancy pants- just come join the fun! Silly awards, serious celebration of love.  If you can't make it in person- join us virtually throughout the month of June and receive a medal and bib!
5K
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JUL 24

Hemingway 5K Sunset Run

Key West, FL
Featured by Runner’s World as one of the Best 5Ks to Run this Summer.    Details: Back for our 37th year!   Runners and walkers enthusiasts can test their skills and celebrate Ernest Hemingway’s sporting lifestyle by joining us in the Conch Republic on July 25-26, 2026 during the in-person Hemingway 5k Sunset Run/Walk! The athletic challenges are part of Hemingway Days, a six-day commemoration of the life and work of the author who lived and wrote in Key West for most of the 1930s.   All participants will start and finish at the iconic Southernmost Point buoy!  Be sure to plan to spend time at our famous after party on the beach!  Don't Forget to Run or Watch the Beer Mile on Sunday!  The most fun event of the week-end!  12PM.
5K
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