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

December 2025
Dec
27
Saturday

The Ritz-Carlton Winter GLO 5k

5 km
January 2026
Jan
3-4
Sa - Su

Wekiwa Springs Ultra

Trail Run 12 hr 24 hr
Jan
7-11
We - Su

Walt Disney World Marathon

5 km 10 km 13 mi 26 mi
Jan
18
Sunday

Jurassic Jog

5 km
Jan
24
Saturday

Monroe Cross Trail 50 Mile Ultra

Trail Run 17 km 50 km 50 mi
Jan
25
Sunday

Town of Celebration Marathon

13 mi 26 mi
Jan - Feb
31-1
Sa - Su

Forgotten Florida

Trail Run 8 mi 15 mi 50 mi 100 mi
February 2026
Feb
7
Saturday

Run for the Cherubs 5K

5 km
Feb
7
Saturday

Super Bowl Duathlon

Duathlon
Feb
20-21
Fr - Sa

Florida ANVIL Ultra Triathlon

Triathlon
Feb
21
Saturday

Real Florida 10K

Trail Run 5 km 10 km
Feb
28
Saturday

Inua 5k Run

5 km
March 2026
Mar
7
Saturday

Shamrock Shuffle - Clermont

5 km 10 km
Mar
7
Saturday

Best Damn Race Orlando

5 km 10 km 13 mi
Mar
7
Saturday

OCBA Law Day 5K

5 km
Mar
8
Sunday

Great Clermont Triathlon

Triathlon
Mar
14
Saturday

HOPE's Sham Rock N Run 5k

5 km
Mar
21
Saturday

The Spring Rising

5 km 10 km
Mar
21
Saturday

Amazing Race For Charity

6 mi
Mar
22
Sunday

AdventHealth Lake Minneola Half Marathon

5 km 10 km 13 mi
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