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Trail Running Calendar near Winter Park 2025-2026

Explore the top trail runs near Winter Park for 2025-2026! We've gathered 146 exciting races in the area. Check out our detailed list below to find your next local race.

April 2026
Apr
25
Saturday

AdventHealth U Run U Pick Blueberry 5K

5 km
Apr
26
Sunday

The Chicken Run 5k

5 km
May 2026
May
2-3
Sa - Su

Sunshine Double

5 km 10 km ... Marathon 50 km
May
2
Saturday

Paws2Run 5K

5 km
May
2
Saturday

US Road Running - DeBary

5 km 10 km Half Marathon
May
9
Saturday

AdventHealth Girlz on Fire Women's Triathlon

Triathlon
May
10
Sunday

Mother's Day 5K - Winter Garden

5 km
May
16
Saturday

US Road Running - DeBary

5 km 10 km Half Marathon
May
23
Saturday

Remember & Honor - Memorial Day 5k

5 km
May
23
Saturday

I Am Enough 5k for Women's Health

5 km
May
30
Saturday

US Road Running - DeLand

5 km 10 km Half Marathon
May
30
Saturday

Dr. Myron L. Rolle Pediatric Gun Safety 5K Walk/Run

5 km
May - Jun
30-5
Sa - Fr

Doughnut Day 5K

5 km
June 2026
Jun
6
Saturday

US Road Running - DeBary

5 km 10 km Half Marathon
Jun
13
Saturday

The Florida Run Trail Race

Trail Run 4 mi 8 mi
Jun
13
Saturday

US Road Running - DeLand

5 km 10 km Half Marathon
Jun
14
Sunday

AdventHealth Cool Sommer Mornings Triathlon

Triathlon
Jun
20
Saturday

US Road Running - DeBary

5 km 10 km 13 mi
Jun
27-28
Sa - Su

Independence Double

Urban Trail 5 km 10 km ... Marathon 50 km
July 2026
Jul
11
Saturday

US Road Running - DeLand

5 km 10 km Half Marathon
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