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Obstacle Race Calendar near Chestertown 2025-2026

Explore the top obstacle runs near Chestertown for 2025-2026! We've gathered 11 exciting races in the area. Check out our detailed list below to find your next local race.

July 2025
Jul
6
Sunday

ASICS Independence Day 4-Miler

4 mi
Jul
12
Saturday

Moonlight 5K

5 km
Jul
12
Saturday

Diamond in the Rough Triathlon

Triathlon
Jul
13
Sunday

BRRC Sweet Air Trail Race

Trail Run 7 mi
Jul
19
Saturday

Great Wyoming Buffalo Stampede

5 km 10 km
Jul
19
Saturday

Endless Summer 6-Hour Run

Trail Run 6 hr
Jul
26
Saturday

Run the Vineyards Bohemia Manor Farm 8K

Trail Run 5 km 8 km
August 2025
Aug
2
Saturday

Half Marathon at Cedar Lane Regional Park

5 km 10 km 15 km 13 mi
Aug
2
Saturday

Casey Cares Foundation 5K Run/Walk

5 km
Aug
10
Sunday

Charm City Run at Boordy Vineyards

5 km
Aug
17
Sunday

Catch-A-Pig 5K

5 km
Aug
17
Sunday

North East Triathlon

Triathlon
Aug
30
Saturday

Charles Street 12

12 mi
September 2025
Sep
6
Saturday

Savage Race - Maryland Fall

Obstacle Run 3 mi 7 mi
Sep
6
Saturday

Half Marathon at Cedar Lane Regional Park

5 km 10 km 15 km 13 mi
Sep
12-14
Fr - Su

Annapolis Run for The Light House

5 km 13 mi
Sep
13
Saturday

Kingdom 5K

5 km
Sep
20
Saturday

Susquehanna River Running Festival

5 km 10 km 13 mi
Sep
20
Saturday

Cancer Warriors 5k

Trail Run 5 km
Sep
21
Sunday

Run Wild for Autism 5K

5 km
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