Name: KISS-IM-MEE 5k
Start: 2026-02-14
End: 2026-02-14
Location: Kissimmee, Florida

About the Event

Kissimmee Main Street is proud to present the 18th Annual Kissimmee 5K, celebrating Valentine’s Day and promoting heart health. A portion of the proceeds will benefit a heart-healthy nonprofit, making every step you take part of a greater cause.

Enjoy a scenic lakeshore run as the early morning mist drifts over beautiful Lake Tohopekaliga. The route winds past Kissimmee’s charming historic homes and through our vibrant downtown, where unique shops and inviting dining spots line the streets. Along the way, you’ll take in some of the best views our historic city has to offer.

This fun, family-friendly event welcomes runners and walkers of all abilities—strollers and leashed pets are encouraged to join the fun!

In the spirit of Valentine’s Day, participants are invited to dress in festive attire and take part in our three lively contests:

Cutest Cupid
Prettiest Pair
Care Club Award – for the largest participating group (church, organization, or business)

Join us as we mark 18 years of fitness, community spirit, and giving back—one heart-healthy step at a time.

Races Offered

Kiss-Im-Mee 5K

Feb 14, 2026

straighten

Distance — 5K

terrain

Type — Running

timer

07:30

sell

$26.00

Kiss-Im-Mee 5K - Virtual Run

Feb 14, 2026

straighten

Distance — 5K

terrain

Type — Running

timer

07:30

sell

$30.00

Kiss-Im-Mee 5k - Seniors (Ages 65 and Over)

Feb 14, 2026

straighten

Distance — Kiss-Im-Mee 5k - Seniors (Ages 65 and Over)

terrain

Type — Running

timer

07:30

sell

$25.00

Kiss-Im-Mee 5k - Student A (Grades K-12 Ages 18 and Under)

Feb 14, 2026

straighten

Distance — 5K

terrain

Type — Running

timer

07:30

sell

$20.00

Kiss-Im-Mee 5k - Student B (College Ages 18 - 24)

Feb 14, 2026

straighten

Distance — Kiss-Im-Mee 5k - Student B (College Ages 18 - 24)

terrain

Type — Running

timer

07:30

sell

$25.00

Weather Overview

These values represent the 3-year monthly averages for February in Kissimmee.

Temp (°C)

Feels Like (°C)

thermostat 13.8° / 24.9°

wb_sunny 12.9° / 23.9°

Wind (km/h)

Humidity (%)

air 10.5 /

water_drop 74.6%

Temp (°C)

Feels Like (°C)

Wind (km/h)

Humidity (%)

thermostat 13.8° / 24.9°

wb_sunny 12.9° / 23.9°

air 10.5 km/h

water_drop 74.6%

About Kissimmee

Kissimmee is a city in Osceola County. Kissimmee is a popular Central Florida tourist destination because of its sunny weather, spring training baseball for major league clubs, and close proximity to Disney World.