Winter Haven
Walking Events Calendar near Winter Haven 2026-2027
Monthly updates for Winter Haven
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Explore the top walking events near Winter Haven for 2026-2027! We've gathered 15 great walks in the area. Check out our detailed list below to find your next local walk.
July 2026
Free informal community walk from HOKA Store Orlando offering 1 mile, 5K, 10K, Half Marathon, or 50K options as part of the free community event.
August 2026
Walkers can choose 5 km or 10 km routes from 2601 E Cherry St in Plant City, FL on a clear local course alongside the running races. Water is only at lap ends and the finish and staff is small with no EMS on site.
September 2026
The event offers a 5K walk at Cypress Cove Nudist Resort as part of a clothing optional experience in a stunning natural setting. Registration includes day fees, check in is available the evening before and the morning of the event, with awards a..
Walkers can choose a 5K course or the 1 mile Memorial Run/Walk; a ruck option involves walking with a weighted rucksack. It starts at Fishhawk Park Square, 6015 Fishhawk Crossing Blvd, Lithia FL 33547 and is open to all ages, fitness levels.
Walkers can join the family friendly 3.1 Miles course starting at Summer House in Golden Oak, Orlando (10350 Dream Tree Blvd). In person participants receive a T shirt, medal, and a post race breakfast alongside the running races.
Walkers can complete a 3.1 Miles route at Celebration Lakeside Park in Celebration, FL. The family friendly event welcomes strollers, children 5 & under are free, and amenities include a t shirt, medal, race bib, race photos and post race breakfa..
October 2026
Walkers can choose the 5K or 10K courses starting at 2601 E Cherry St, Plant City FL. The course is clear and local with limited water stations at the end of each lap and at the race finish and no EMS stationed on site.
November 2026
December 2026
Walkers can do the 5k that starts and finishes at Keel and Curley Winery in Plant City. The scenic two loop farm course mixes grass, dirt, gravel and pavement, passes through blueberry fields, can be muddy, and welcomes walkers alongside the runn..
February 2027
Walkers can choose Half Marathon, 10K, or 5K, starting at Frostproof Middle High School on courses that are over 90% hard packed clay with aid stations for four hours.
March 2027
Walkers can choose the 1.5 Miles Cider Walk at Keel Farms in Plant City, enjoying the scenic farm landscape and cider themed surroundings. Multiple start times are selectable during registration and walkers receive a t shirt, cider donut and a po..