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Kentucky Trail Running Calendar 2026-2027

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Monthly updates for Kentucky

Get new running races (and updates) in your inbox every month.

Explore the best trail runs in Kentucky for 2026-2027! Our updated list features 48 exciting races across the region. Find your next race in Kentucky below and join the running community at these great events!

August 2026
Aug
30
Su

Blackacre Barnstormer

Trail Run 4 mi 8 mi
September 2026
Sep
5
Sa

GRC Cross Country Daniel Boone 5K

Trail Run 5 km
Sep
19
Sa

Pride Run Lexington

Trail Run 3 mi
Sep
20
Su

Spoonbread Festival 5K

Urban Trail 3 mi
Sep
20
Su

The Lookout

Trail Run 3 mi 8 mi
Sep
26
Sa

Run Baby Run 5K - Lexington

Trail Run 5 km
Sep
26
Sa

Yeti Trail Run 30K

Trail Run 5 km 10 km 13 mi 30 km
Sep
27
Su

The Raven 10k

Trail Run 10 km
October 2026
Oct
3
Sa

The Rugged Red Trail Half Marathon

Trail Run 13 mi
Oct
3
Sa

The Wildcat @ General Butler

Trail Run 5 km 10 km 13 mi
Oct
4
Su

Kentucky Cryptid Series

Trail Run 5 mi 8 mi
Oct
10
Sa

Forkland Festival Fox and Hound 4k

Trail Run 4 km
Oct
10
Sa

Run The Ridge Trail Race

Trail Run 5 km 10 km 25 km
Oct
17
Sa

The Running Pumpkin

Trail Run 5 km
Oct
17
Sa

LBL Bridge to Bridge Trail Run

Trail Run 22 km
Oct
24
Sa

Mammoth Cave 50k/25k

Trail Run 25 km 50 km
Oct
25
Su

Stone Steps 50K and 27K Trail Run

Trail Run 27 km 50 km
Oct
25
Su

Little Batty Trail Run

Trail Run 5 km 10 km 13 mi
Oct
31
Sa

Haunted Trail Run 10k

Trail Run 5 km 10 km
November 2026
Nov
14
Sa

Turkey Trails - Cincinnati

Trail Run 5 km 10 km 13 mi
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