Kissimmee
Walking Events Calendar near Kissimmee 2026-2027
Monthly updates for Kissimmee
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Explore the top walking events near Kissimmee for 2026-2027! We've gathered 66 great walks in the area. Check out our detailed list below to find your next local walk.
March 2027
Walkers can choose 10K or 5K on the flat out and back South Lake Trail along Lake Minneola, starting at Waterfront Park, Clermont; aid stations open four hours.
April 2027
Participants may choose in person or virtual 5K options, with the in person course starting at 2501 General Rees Ave in Orlando. The family friendly event is held alongside the fun run and raises funds for Paving the Way Foundation prevention edu..
Walkers follow an out and back on hard packed clay roads at Southern Hill Farms in Clermont FL, covering 5K (listed as 3.1 miles). The event includes a free pancake breakfast and a pint of u pick blueberries at the venue; virtual entries excl..
Walk the scenic 5K through downtown Orlando finishing at Lake Eola Park, with a Walker start on N. Eola Drive, purple bibs, team and virtual options.
May 2027
Walkers follow a 5K route across the back 9 of Grande Lakes resort golf course in Orlando, with free self parking, valet option, post event snacks and stretching and massage.