Chepstow close

Trail Running Calendar near Chepstow 2026-2027

Header image
Monthly updates for Chepstow

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

Explore the top trail runs near Chepstow for 2026-2027! We've gathered 84 exciting races in the area. Check out our detailed list below to find your next local race.

January 2026
Jan
12
Mo

The Slothful Run

Trail Run 5 km 10 km Half Marathon Marathon
Jan
12-18
Mo - Su

The 7 Deadly Sins 7in7

Trail Run 5 km 10 km Half Marathon Marathon
Jan
13
Tu

The Proud Run

Trail Run 5 km 10 km Half Marathon Marathon
Jan
14
We

The Lusty Run

Trail Run 5 km 10 km Half Marathon Marathon
Jan
15
Th

The Angry Run

Trail Run 5 km 10 km Half Marathon Marathon
Jan
16
Fr

The Gluttonous Run

Trail Run 5 km 10 km Half Marathon Marathon
Jan
17
Sa

The Greedy Run

Trail Run 5 km 10 km Half Marathon Marathon
Jan
17
Sa

Dark Skies Series

Trail Run 5 km 10 km
Jan
18
Su

Riverbank Rollick

Trail Run 10 mi
Jan
18
Su

The Envious Run

Trail Run 5 km 10 km Half Marathon Marathon
Jan
18
Su

CF64 Winter Race

Trail Run 10 km
Jan-Feb
31-1
Sa - Su

May Hill Massacre

Trail Run 7 mi 14 mi
February 2026
Feb
7
Sa

Westonbirt Arboretum Winter Night Race

Trail Run 5 km 10 km
Feb
8
Su

Westonbirt Arboretum Winter Day Race

Trail Run 5 km 10 km
Feb
8
Su

Muddy Woody

Trail Run 6 mi
Feb
8
Su

Wiltshire 10

Trail Run 10 mi
Feb
20
Fr

Phoenix Running - Brimscombe

Trail Run 5 km 10 km Half Marathon Marathon
Feb
22
Su

Two Tunnels Races

Trail Run 5 km 10 km ... Marathon 50 km
Feb
22
Su

Ironwood Challenge

Trail Run
Feb
22
Su

Sorbrook Slog

Trail Run 7 mi