15 running and walking events in Key West, Florida

• 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.

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'!

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

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

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.

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!!

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.

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

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.

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!