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Running Calendar near Longwood 2025-2026

Explore the top running races near Longwood for 2025-2026! We've gathered 105 exciting races in the area. Check out our detailed list below to find your next local race.

May 2026
May
2
Saturday

The Tick

Trail Run 57 mi
May
2-3
Sa - Su

Sunshine Double

5 km 10 km ... 42 km 50 km
May
10
Sunday

Mother's Day 5K - Winter Garden

5 km
May
23
Saturday

Remember & Honor - Memorial Day 5k

5 km
September 2026
Sep
26
Saturday

Margaritaville Run Orlando 10K

5 km 10 km 21 km
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