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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 27 exciting races across the region. Find your next race in Kentucky below and join the running community at these great events!

January 2026
Jan
17
Sa

Shelby Trails - Simpsonville, KY

Trail Run 4 mi 8 mi
February 2026
Feb
7
Sa

Louisville Lovin' The Hills

Trail Run 6 mi 15 mi 50 km
March 2026
Mar
12-14
Th - Sa

Warbird 100

Trail Run 104 mi
Mar
14
Sa

Land Between The Lakes Trail Runs

Trail Run 23 km Marathon 60 km 50 mi
Mar
21
Sa

Lucky O'possum

Trail Run 5 km 10 km Half Marathon
Mar
28
Sa

Bourbon Country 50k

Trail Run 5 km 25 km 50 km
April 2026
Apr
11
Sa

Saunders Springs Shootout

Trail Run 5 km 10 km 20 km 30 km
Apr
11
Sa

Howlin' Wolfe 50k

Trail Run 25 km 50 km
Apr
19
Su

Dirt Days Trail Series - Ault Park Switchback

Trail Run 4 mi
Apr
26
Su

Backside Trail Marathon - Louisville, KY

Trail Run 13 mi 26 mi
May 2026
May
2
Sa

The Wildcat @ General Butler

Trail Run 5 km 10 km ... Half Marathon 6 hr
May
9
Sa

Laurel Lake 10k

Trail Run 45 mi
May
17
Su

Dirt Days Trail Series - Mt. Airy Ridge Run

Trail Run 5 mi 11 mi
June 2026
Jun
13
Sa

Gavin's Gallop 5K

Trail Run 5 km
Jun
21
Su

Dirt Days Trail Series - French Park Creek Crossings

Trail Run 4 mi
Jun
27
Sa

The Ascent Red River Gorge 5K

Trail Run 5 km
August 2026
Aug
28
Fr

Cabernet Canter Cross Country 10K

Trail Run 5 km 10 km
September 2026
Sep
20
Su

Spoonbread Festival 5K

Urban Trail 5 km
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 20 km 30 km