Chepstow
Trail Running Calendar near Chepstow 2026-2027
Explore the top trail runs near Chepstow for 2026-2027! We've gathered 139 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
February 2027
A winter adventure race in the Cotswolds combining trail running and mountain biking with map and compass navigation, solo or team entries and bike hire available.
About sixish hilly country miles of off road trails above Long Ashton with chip timing, limited parking, and a charitable donation from each entry.
Trail runs and standard and sprint off road duathlons take place in the forest around Speech House, Gloucestershire.
March 2027
Trail running event in the Black Mountains with marked 10, 20 and 40 mile routes from Crickhowell, marshals, stocked checkpoints and strict mandatory kit requirements; canicross friendly and GPX routes available.
Six hour trail loop challenge at Symonds Yat Rock, repeat a 5.25 km loop with 160 m climb, aid station each lap and medals for six, nine and twelve completed loops.
Annual March challenge walk around Abergavenny with four route options from about 10 to 20 miles, mountain checkpoints and charity fundraising.
A fell race near Goodrich covering 8.6 km with 335 m ascent, listed in the South Wales Winter Hill Series with entry fees for members and non-members.
A way marked Forest of Dean half marathon around Speech House on forest trails, with TRA championship and England Athletics qualifier status and proceeds to charity.
April 2027
A 15 miles off road fell race across the Mendip Hills from Cheddar with over 2000 feet of climbing, TRA licensed and supporting local charities.
A point to point 200 miles trail race across South Wales from Chepstow to Worm's Head, with a 120 hour limit, 30,000 ft climb, eight aid stations and live tracking.
A last-person-standing Backyard Ultra at the Medieval Village, Cosmeston Lakes: runners repeat a fixed 6706 m loop each hour until one athlete completes one more loop than anyone else. Camping and on-site facilities are provided.