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Walking Events Calendar near Winter Park 2026-2027

Monthly updates for Winter Park

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Explore the top walking events near Winter Park for 2026-2027! We've gathered 99 great walks in the area. Check out our detailed list below to find your next local walk.

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
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.
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