1 event in Kissimmee, Florida

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:

1. Cutest Cupid

2. Prettiest Pair

3. 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.