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Running Calendar near Windermere 2026-2027

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Explore the top running races near Windermere for 2026-2027! We've gathered 165 exciting races in the area. Check out our detailed list below to find your next local race.

Half Marathons Marathons Trail Runs Triathlons
August 2026
Aug
15
Sa

US Road Running - DeBary

Road Race 5 km 10 km 13 mi
Aug
15
Sa

Track Shack's Celebration of Running 5K

Road Race 5 km
Aug
16
Su

Formosa Brew Run 5K

5 km
Aug
22
Sa

Pride of the Patriots 5K

3 mi
Aug
22
Sa

Faith & Fitness 5K

Road Race 5 km
Monthly updates for Windermere

Get new running races (and updates) in your inbox every month.
Aug
23
Su

Lake Nona Tri-Nona Triathlon

Triathlon Sprint 440 m 11 mi Sprint 440 m 11 mi 5 km Sprint 1 11 mi 5 km
Aug
25
Tu

AdventHealth University 3K Walk/Run

3 km
September 2026
Sep
5-7
Sa - Mo

Labor Day Triple

3 mi 6 mi ... 26 mi 50 km
Sep
5
Sa

Run the Resort 5K

5 km
Sep
5
Sa

US Road Running - DeBary

Road Race 5 km 10 km 13 mi
Sep
5
Sa

Cypress Cove Labor Day 5K

Road Race 5 km
Sep
6
Su

The Ritz-Carlton Grande Labor Day Weekend 5K

Road Race 5 km
Sep
6
Su

Labor Day 5K - Orlando

5 km
Sep
6
Su

Big Red Chair Sprint Triathlon

Triathlon Super sprint 200 m 4 mi 5 km
Sep
12
Sa

BrooklynRoseStrong 5K

Road Race 5 km
Sep
12
Sa

Tunnel to Towers 5K - Orlando, FL

Road Race 5 km
Sep
12
Sa

US Road Running - Orlando

Road Race 5 km 10 km
Sep
12
Sa

Back-to-School Bash - Eustis

Trail Run 2 mi 3 mi
Sep
12
Sa

Freeway 5K Run for Recovery

5 km
Sep
13
Su

AdventHealth Cool Sommer Mornings Triathlon Series

Road Race 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
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