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Walking Events Calendar near Winter Garden 2026-2027

Monthly updates for Winter Garden

Get new walking events (and updates) in your inbox every month.

Explore the top walking events near Winter Garden for 2026-2027! We've gathered 93 great walks in the area. Check out our detailed list below to find your next local walk.

August 2026
Aug
8
Sa

US Road Running - Orlando

Road Race Walk 5 km 10 km
Aug
8
Sa

Triple-H 5K Run and Walk

Road Race Walk 3 mi
Aug
9
Su

Cool Sommer Mornings 5K Series

Road Race Walk Triathlon Sprint 440 m 5 km Sprint 440 m 8.2 mi Sprint 440 m 8.2 mi 5 km Sprint 1 8.2 mi 5 km
Aug
15
Sa

US Road Running - DeBary

Road Race Walk
Aug
15
Sa

Track Shack's Celebration of Running 5K

Road Race Walk 5 km
Aug
22
Sa

Faith & Fitness 5K

Road Race Walk 5 km
September 2026
Sep
5
Sa

US Road Running - DeBary

Road Race Walk
Sep
5
Sa

Cypress Cove Labor Day 5K

Road Race Walk 5 km
Sep
6
Su

The Ritz-Carlton Grande Labor Day Weekend 5K

Road Race Walk
Sep
12
Sa

BrooklynRoseStrong 5K

Road Race Walk 5 km
Sep
12
Sa

Tunnel to Towers 5K - Orlando, FL

Road Race Walk 5 km
Sep
12
Sa

US Road Running - Orlando

Road Race Walk
Sep
13
Su

AdventHealth Cool Sommer Mornings Triathlon Series

Road Race Walk Triathlon Sprint 0.25 3.1 mi Sprint 0.25 8.2 mi Sprint 0.25 8.2 3.1 mi Sprint 1 8.2 3.1 mi
Sep
18
Fr

Howl-O-Sprint 5K Run

Road Race Walk 5 km
Sep
19
Sa

US Road Running - DeBary

Road Race Walk
Sep
19
Sa

Miles To Go 5K

Road Race Walk 3 mi
Sep
19
Sa

Run Nona 5K & Nemours Children's Run

Road Race Walk
Sep
20
Su

Fast and the Furriest 5K

Road Race Walk 3 mi
Sep
20
Su

Superhero Race Against Cancer 5K

Road Race Walk
Sep
26
Sa

Battle of the Bands 5K

Road Race Walk
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