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Obstacle Race Calendar near Longwood 2025-2026

Explore the top obstacle runs near Longwood for 2025-2026! We've gathered 125 exciting races in the area. Check out our detailed list below to find your next local race.

March 2026
Mar
14
Saturday

Sham Rock N Run 5k

5 km
Mar
15
Sunday

Lucky Charm 5K

5 km
Mar
15
Sunday

Lookin for a Cure Orlando

5 km
Mar
21
Saturday

The Spring Rising

5 km 10 km
Mar
21
Saturday

Amazing Race For Charity

3 mi
Mar
22
Sunday

AdventHealth Lake Minneola Half Marathon

3 mi 6 mi 13 mi
April 2026
Apr
4
Saturday

Grand Living Park at Lake Mary 5k Fun Run and Walk

5 km
Apr
4
Saturday

Dream Finders Homes Hippity Hop 5K

5 km
Apr
11
Saturday

Red Bug Lake Park 5K Run/Walk

5 km
Apr
12
Sunday

The Great American Bacon Race - Orlando

5 km
Apr
26
Sunday

The Chicken Run 5k

5 km
May 2026
May
2
Saturday

The Tick

Trail Run 57 mi
May
2-3
Sa - Su

Sunshine Double

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

Paws2Run 5K

5 km
May
10
Sunday

Mother's Day 5K - Winter Garden

5 km
May
23
Saturday

Remember & Honor - Memorial Day 5k

5 km
May
30
Saturday

US Road Running - DeLand

5 km 10 km Half Marathon
May - Jun
30-5
Sa - Fr

Doughnut Day 5K

5 km
May
31
Sunday

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

5 km
June 2026
Jun
27-28
Sa - Su

Independence Double

Urban Trail 5 km 10 km ... Marathon 50 km
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