Winter Springs close

Trail Running Calendar near Winter Springs 2025-2026

Explore the top trail runs near Winter Springs for 2025-2026! We've gathered 107 exciting races in the area. Check out our detailed list below to find your next local race.

May 2026
May - Jun
30-5
Sa - Fr

Doughnut Day 5K

5 km
June 2026
Jun
13
Saturday

US Road Running - DeLand

5 km 10 km Half Marathon
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
August 2026
Aug
8
Saturday

US Road Running - DeLand

5 km 10 km Half Marathon
September 2026
Sep
26
Saturday

Margaritaville Run Orlando 10K

5 km 10 km Half Marathon
Sep
27
Sunday

Hickory Hammock 5K

5 km
Articles
Top 10 Marathons in the Netherlands — The Ultimate Dutch Marathon Bucket List: 10 Unmissable Races
The Beauty of the Easy Run — Why slowing down might be the smartest thing you do for your running
Mizuno Wave Rider 28: Elevating the Legacy of a Running Icon
Garmin Forerunner Review: Garmin Forerunner Series