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Walking Events Calendar near Winter Garden 2026-2027

Monthly updates for Winter Garden

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Explore the top walking events near Winter Garden for 2026-2027! We've gathered 68 great walks in the area. Check out our detailed list below to find your next local walk.

March 2027
Mar
14
Su

Formosa Spiked Apple 5K

Trail Run Walk 5 km
Walkers follow a 5K course at Formosa Winery through vineyard and fruit orchards on winery grounds. Walkers may choose their start time during registration and share the event with the run while receiving cider and a cider donut.
Mar
20
Sa

The Spring Rising

Road Race Walk 3 mi
Walkers can choose 3.1 Miles, 6.2 Miles or a short 1 Miles route starting at First United Methodist Church Oviedo, 263 King St., Oviedo FL. Routes are out and back along the Cross Seminole Trail past local landmarks, with a post race Gard..
Mar
21
Su

AdventHealth Lake Minneola Half Marathon

Road Race Walk
Walkers can choose Half Marathon (13.1 miles), 10K, or 5K routes starting at Waterfront Park, 100 3rd Street, Clermont FL 34711. All courses are flat out and back on the South Lake Trail along portions of Lake Minneola with on course ente..
April 2027
Apr
3
Sa

Run with Howie 5k Fun Run

Road Race Walk 3 mi
Walkers can complete the 3.1 Miles course at Oviedo Mall, 1700 Oviedo Mall Boulevard, on a professionally organized route with community activities and sponsor booths nearby. The walk runs alongside the 5K races and benefits the PTSA.
Apr
10
Sa

Light the Path Fun Run

Road Race Walk 5 km
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..
Apr
24
Sa

AdventHealth U Run U Pick Blueberry 5K

Road Race Walk 3 mi
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..
May 2027
May
15
Sa

Hero Hustle 5K

Road Race Walk 5 km
Walkers follow a chip timed 5K course of 3.1 miles through scenic DeBary neighborhoods, starting at 398 S. Shell Rd. Packet pick up is available Friday at the DBK Home Office and on race day, and all 5K finishers receive custom diecast medals.
May
29
Sa

Remember & Honor - Memorial Day 5k

Road Race Walk
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