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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 183 exciting races in the area. Check out our detailed list below to find your next local race.

Half Marathons Marathons Trail Runs Triathlons
March 2027
Mar
14
Su

The Grande Lakes Lucky Stride 5K & Master Yoga Class

5 km
Mar
14
Su

Dream Finders Homes Lucky Charm 5K & 10K

5 km 10 km
Mar
20
Sa

The Spring Rising

3 mi 6 mi
Mar
21
Su

AdventHealth Lake Minneola Half Marathon

3 mi 6 mi 13 mi
Mar
27
Sa

Dream Finders Homes Hippity Hop 5K

5 km
Monthly updates for Windermere

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April 2027
Apr
3
Sa

Amazing Race For Charity

5 mi
Apr
3
Sa

Run with Howie 5k Fun Run

3 mi
Apr
9-11
Fr - Su

runDisney Springtime Surprise Weekend

5 km 10 km 10 mi 19 mi
Apr
10
Sa

Light the Path Fun Run

5 km
Apr
10
Sa

Wounded Warfighter Lone Sailor 5K/10K

5 km 10 km
Apr
10
Sa

Last Man Standing Orlando

Backyard Ultra 4 mi
Apr
10
Sa

Bahia Shrine Camel Walk/Run

5 km 4 mi
Apr
24
Sa

AdventHealth U Run U Pick Blueberry 5K

5 km
Apr
29
Th

AdventHealth Corporate 5K

5 km
May 2027
May
1-2
Sa - Su

Sunshine Double

5 km 10 km ... 26 mi 50 km
May
1
Sa

Ole Ole 5K - Orlando

3 mi
May
8
Sa

Girlz on Fire Women's Triathlon

Triathlon Aquathlon (Swim-Run) 0.25 3.1 mi Aquabike (Swim-Bike) 0.25 8.2 mi Sprint 0.25 8.2 3.1 mi Sprint 1 8.2 3.1 mi
May
8
Sa

Run for the Trees Jeannette Genius McKean Memorial 5K

Road Race Trail Run 5 km
May
9
Su

Mother's Day 5K - Clermont

5 km
May
15
Sa

Hero Hustle 5K

5 km
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