10 walking events in Key West, Florida

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

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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
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

Earth Day 5K Run/Walk [southernmostrunners.com] [Register at runsignup.com]
Sat, Apr 18, 2026 at 8:00 AM

Description

Come join us for the 28th Annual Earth Day 5K Run/Walk!! This event benefits the Conch Republic Marine Army, an incredible organization who works on cleaning and restoring the mangrove habitats of...

Come join us for the 28th Annual Earth Day 5K Run/Walk!! This event benefits the Conch Republic Marine Army, an incredible organization who works on cleaning and restoring the mangrove habitats of the Florida Keys. Check out their incredible efforts and sign up to participate with them by clicking the link here! https://www.conchrepublicmarinearmy.org/

The event will be held on Saturday, April 18, 2026, at 8:00 am. The run begins and ends near the Ingham ship, following 3 loops of the promenade at the beautiful Truman Waterfront Park. There will be awards for age-group winners along with a raffle of incredible local prizes that all participants will automatically be entered in. T-Shirts will be available to the first 150 participants so don't wait to sign up!

Pre-Registration & Packet Pickup will be on Friday, April 17th 4:30pm - 6:30pm at the Truman Waterfront Park by the Ingham.

RACE DAY Registration & Packet Pickup will be on site on Saturday, April 18th 7:00 am - 7:45am.

Additionally, please bring your old running shoes as we've teamed up with Sneakers4Good to give your running shoes new life and keep them out of the landfill. Sneakers4Good takes the running shoes and sneakers collected in their programs and ship them to micro-entrepreneurs in 27 developing countries. They then clean and resell the sneakers to support their small businesses. How cool!!

3.1 Miles 5k Run Walk
Key West, Florida, 33040, United States
OpenStreetMap Google Maps
Mariners March 5K Run/Walk [keywest5k.com] [Register at runsignup.com]
Sat, Apr 25, 2026 at 8:00 AM

Description

What: 15th Annual Mariners March is a 5K Run/Walk and Children's Fun Run to benefit The Basilica School of St. Mary Star of the Sea.

When: Saturday April 25, 2026

Where: Starts and ends at the...

What: 15th Annual Mariners March is a 5K Run/Walk and Children's Fun Run to benefit The Basilica School of St. Mary Star of the Sea.

When: Saturday April 25, 2026

Where: Starts and ends at the Basilica School of St. Mary Star of the Sea 700 Truman Ave. Course map below.

Packet pickup on Friday April 24th from 4:30-6:30pm @ the Basilica School

Race Day Packet pickup and registration @ Basilica 7:00-7:45am

Pre-Race Day Registration $30

Day of Race $35

Under 18 $20

Free kids fun run for 9 and under.

Free shirt for the first 100 registrants and all finishers receive a finishing medal.

3.1 Miles 5k Fun Run Run Walk
700 Truman Ave, Key West, Florida, 33040, United States
OpenStreetMap Google Maps
Run for Rhonda [runforrhonda.com] [Register at runsignup.com]
Sun, May 03, 2026 at 8:00 AM

Description

Join Us for the 3rd Annual Run for Rhonda 5K!

Grab your brightest colors and your best fiesta energy because this year, we’re turning the streets into a celebration of Rhonda’s legacy.

This...

Join Us for the 3rd Annual Run for Rhonda 5K!

Grab your brightest colors and your best fiesta energy because this year, we’re turning the streets into a celebration of Rhonda’s legacy.

This family-friendly event, offering something for everyone, will take place on Sunday, May 3, 2026.

🌮 5K, 1‑Mile Fun Run & a ¼ Mile Run for Fun for the Kiddo’s

🍹Margaritas waiting at the finish line

🎭Costume contest, DJ, food, drinks & nonstop fun

Every step we take honors Rhonda’s commitment to Fitness, Education and Fellowship—and every registration helps fund a scholarship for a local female athlete through the Take Stock In Children - Monroe County program. Her legacy keeps moving forward because our community shows up with heart.

The run begins and ends near the Ingham Ship, following 3 loops of the promenade at the beautiful Truman Waterfront where there is plenty of room to move and lots for kids to enjoy at the playground and splash park.

Every registered runner receives a swag bag filled with goodies from our incredible sponsors. You will also automatically be entered into a draw to win a fabulous prize!

Stick around after the race for an exciting fiesta after-party and music by DJ Jimmy Jamz!

🎽 Register Early! The first 50 registrants over 12 will receive a memorial Run for Rhonda T-shirt!

🏅Awards & Prizes:

· 5K Overall Male & Female Runners receive winner’s medals.

· 5K Top 3 Overall Male & Female Walkers receive winner's medals.

· 5K Top 3 in age group Male & Female Finishers receive winner's medals.

Age Groups are: 0-14, 15-19, 20-29, 30-39, 40-49, 50-59, 60+

· 1 Mile Top 3 Overall Male & Female Finishers receive winner's medals

· 1 Mile 12 & under Top 3 Overall Male & Female Finishers receive winner's medals

🌟 Fiesta Fun & Costume Contest! 🌟

50/50 raffle winner - raffle tickets sold on the day or at packet pick up Saturday.

Best Costume (Ages 0-14) Best Costume (Ages 15 and up)

🏃🏻‍♂️ Race Details:

Check-in: 7:00 AM

Race Start: 8:00 AM

5K: 3 loops of the promenade

1 Mile: 1 loop of the promenade (will start shortly after the 5K)

Walkers and runners will start together. Participants will receive one of three different colored bibs to clearly identify their category: 5K Runner, 1-Mile Runner, or Walker (5K or 1-Mile).

Chipped Timing: Live results posted immediately after the race.

We will have water available from FKAA and a water station available for you to fill your own bottles.

Volunteer: Not big into running, but you would still love to help? Click on the “Volunteer” tab at the top to check out the available volunteer opportunities!

Packet Pick up

Location: Truman Waterfront under the tent on the grassy area near the parking lot closest to the Ingham ship.

Date & Time: Saturday May 2nd, 2pm-4pm

Sunday May 3rd, 7am-7:45am

Additional Run for Rhonda T-shirts, tanks and sweatshirts for purchase

https://www.bonfire.com/run-for-rhonda-5k/

Don't miss out - sign up today and help us award the 3rd annual Rhonda Flores Memorial Scholarship to a local student!

#RunForRhonda #FiestaFun

1 Miles 5k Fun Run Run Walk
Key West, Florida, 33040, United States
OpenStreetMap Google Maps
Menendez Miler 5K Run/Walk [southernmostrunners.com] [Register at runsignup.com]
Sat, May 09, 2026 at 8:00 AM

Description

Benefiting: Sunset Rotary Bobby Menendez Scholarship Fund

5K run/walk starting at Truman Waterfront near the Ingham with 3 loops around the park. See course map below.

First 100 entrants receive a...

Benefiting: Sunset Rotary Bobby Menendez Scholarship Fund

5K run/walk starting at Truman Waterfront near the Ingham with 3 loops around the park. See course map below.

First 100 entrants receive a free T-Shirt!

Pre-race packet pick up will be on Friday, May 8th from 5:30-7:30 PM at Truman Waterfront

Race day packet pick up and check-in 7:00 AM at Truman Waterfront in front of the Coast Guard Cutter Ingham

Medals: Awarded to Overall M & F Winners,

Masters M & F Winners,

Top 2 M & F in each 10 year age group for 5K runners

Top 2 M & F walkers.

5k Run Walk
Southard Street And Butler Boulevard, Key West, Florida, 33040, United States
OpenStreetMap Google Maps
KEYS100 Ultramarathon [keys100.com] [Register at runsignup.com]
Sat, May 16, 2026 at 5:00 AM

Description

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...

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? We've saved a space for

you!

50k 50 Miles 100 Miles Marathon Run Ultra Walk
Key West, Florida, 33340, United States
OpenStreetMap Google Maps
Hemingway 5K Sunset Run [keywesthalfmarathon.com] [Register at runsignup.com]
Sat, Jul 25, 2026 at 7:30 PM

Description

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...

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.

3.1 Miles 5k Run Walk
Southernmost Point, Key West, Florida, 33040, United States
OpenStreetMap Google Maps
2nd Annual Save Our First Responders 5K [saveourfirstresponders.org] [Register at runsignup.com]
Sat, Jan 09, 2027 at 8:00 AM

Description

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...

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 33040

WEBSITE & 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 Investigators; EMTs, Paramedics & Nurses; Firefighters; Law Enforcement Officers; and the USA Armed Forces.

SPECIAL PARTICIPANTS: We are blessed to welcome back MCSO Bureau of Corrections Major Tim Age, Captain Crane, Lieutenant Rice, and FWC Lieutenant Jeremy Munkelt to the starting line!

AWARDS & RECOGNITION

FINISHER MEDALS: All participants who complete the 5K will receive a commemorative finisher medal.

OFFICER ALIOHT VALDES MARRERO PERPETUAL TROPHY: Presented by Key West City Commissioner Donald 'Donie' Lee to the winning "Super Eight" team.

TEAM AWARDS: Monroe County Sheriff Rick Ramsay will award trophies and medals (gold, silver, bronze) to the top 3 first responder teams.

INDIVIDUAL MEDALS: Awarded to top overall and age-group winners (Male/Female).

YOUTH VOLUNTEER RECOGNITION: Major Tim Age will recognize the heart of our mission—our youth volunteers from the Florida Keys Sea Cadets with signed certificates of achievement and hero medals.

SCHEDULE & LOGISTICS

PACKET PICKUP:

Friday, January 8th (5 PM - 7 PM): Fit2Run "The Runner’s Superstore" at 211 Duval Street.

Race Day, January 9th (6:45 AM - 7:45 AM): Truman Waterfront.

RACE DAY SCHEDULE:

Opening Ceremony: Featuring a special invocation by Bishop Jonathan Carey, praying for the protection and wellbeing of all first responders and their families.

Guest Speaker: We are honored to welcome back Command Sergeant Major Tonya Oxendine (Wounded Warrior Project) to share her message of resilience.

After the Race: Refreshments and a raffle. Participants are encouraged to join the Wounded Warrior Project Soldier Ride community ride in Key West following our closing ceremonies.

PERKS & SUPPORT

T-SHIRTS & GEAR: The first 200 entrants will receive a free t-shirt and a customized souvenir drawstring backpack.

CHARITY SUPPORT: Save Our First Responders is a program of The Florida Correctional Officers Association, Inc., a 501(C)(3) public charity. Your support directly funds mental health resources.

Join us in celebrating and supporting these frontline heroes! Thank you and may God bless and protect us all!

Race Contact: saveourfirstresponders@gmail.com

5k Run Walk
Key West, Florida, 33040, United States
OpenStreetMap Google Maps

Local Clubs & Organizations

Bone Island Swim Club Club

[cfk.edu] [usaswimming.org]
USA Swimming Club. 3 members.

Swim

Contact: lori.bosco@cfk.edu
5901 College Rd, Key West, Florida, 33040-4315, United States
OpenStreetMap Google Maps
Phone: +1 305-809-3562
College of the Florida Keys Club

[cfk.edu] [usaswimming.org]
USA Swimming Club. 2 members.

Swim

Contact: lori.bosco@cfk.edu
5901 College Rd, Key West, Florida, 33040-4315, United States
OpenStreetMap Google Maps
Phone: +1 305-360-2124

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