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Trail Running Calendar near Jackson 2025-2026

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Explore the top trail runs near Jackson for 2025-2026! We've gathered 42 exciting races in the area. Check out our detailed list below to find your next local race.

July 2025
Jul
26
Saturday

Shepherd's House Run for Recovery

5 km
Jul
26
Saturday

Run White & Blue 10K

5 km 10 km
August 2025
Aug
8
Friday

Radler Rush Cross Country 10k

5 km 10 km
Aug
8
Friday

Blazing Blue Devil 5K

5 km
Aug
9
Saturday

A Midsummer Night's Run

5 km
Aug
10
Sunday

Kentucky Senior Games 10k

10 km
Aug
15
Friday

Gallop & Glow 5K

5 km
Aug
16
Saturday

Pioneer Days 5K - Harrodsburg

5 km
Aug
23
Saturday

Triple Crown Trot

5 km
Aug
23
Saturday

CASA Superhero Run - Versailles

5 km
Aug
23
Saturday

Half Marathon at Millennium Park

5 km 10 km 13 mi
Aug
29
Friday

Cabernet Canter Cross Country 10K

Trail Run 5 km 10 km
September 2025
Sep
5
Friday

Run To Remember - Frankfort

5 km
Sep
6
Saturday

Lexington Equine Medical Hunter Pace

5 km
Sep
13
Saturday

Run For A Cause 5K

5 km
Sep
14
Sunday

Kentucky Army National Guard 5k/10k

5 km
Sep
14
Sunday

Fly Sam Fly 5K

5 km
Sep
20
Saturday

Wildman Triathlon Experience

Triathlon
Sep
20
Saturday

Run4DC

5 km
Sep
27
Saturday

Harrodsburg Oktoberfest 5K

5 km
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