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.
November 2026
Off-road 5 km and 10 km races plus a 500 m kids run and a daytime canicross around the Bath Skyline with marked muddy trails and finisher medals.
Night orienteering at Clevedon Court Estate on 14 November 2026 with a 60 minute score course, 30 controls and a lateness penalty of 1 point per 6 seconds.
A Movember charity run at Ashton Court Park offering 1.5k, 5k, 10k and half marathon options with chip timing, medals and headbands, mixed path and trail terrain, some hilly sections, and on course refreshments.
Trail trail race from Bath Racecourse offering a two-lap hilly half marathon and a single-lap Ultra 10km with significant elevation and on course aid stations.
Night orienteering at Symonds Yat combining a 60 minute Western Night League score event with the Army Night Championships on mapped forest terrain.
A 5.7 km fell race in Llanfoist with 485 m ascent, limited to 120 runners; entry fees £6/£4 and no entries on the day.
Two trail distances on 28 November 2026 around Machen, featuring wooded single track, ridgeway exposure and steep climbs. The half course is fully marked while the marathon requires self navigation with marshals at key points.
Lap-based timed event at Parc Taf Bargoed on 28 November 2026 offering flexible distances from a 5.3 km lap up to ultra, with medal and no medal entry options.
A new out and back 10 km along the River Wye in Hereford on 28 November 2026, mainly off road with a bespoke finisher medal and post-race refreshments.
Forest orienteering at Weston Woods with eight courses from 1.0 km to 5.4 km, organised by Bristol Orienteering Klub and entered online via Pre entries.
A family-friendly muddy fun run in Almondsbury with 5K, 2K and a mini mile, a dog-friendly wave, charity support and on-site activities.
December 2026
Part of a 12 Days of Christmas series at Pengethley Manor in Ross on Wye offering 5k, 10k, half marathon, marathon and ultra distances on a tough off road loop. Runners and walkers have seven hours to complete their chosen distance with virtual optio..
A festive 5 km off road Santa Dash at Tinkley Gate raising funds for Allsorts, with fancy dress, a 2.5 km child lap, café and on site parking.
A 12-day consecutive running challenge at Pengethley Manor, Ross-on-Wye, with daily choices from 5k to ultra on a 2.5 km lap offroad course. Each day has a unique medal and there are in-person and virtual entry options.
Part of a themed Christmas series at Pengethley Manor, this offroad event offers distances from 5k to ultra with a seven hour completion limit and both on site and virtual entry options.
Part of a 12-day Christmas race series at Pengethley Manor, offering 5k, 10k, half, marathon and ultra options on a 2.5 km lap off-road course. Walkers and runners have a seven hour time limit and paid entries receive a medal.
Part of a 12 Days of Christmas race series at Pengethley Manor, this offroad event offers distances from 5k to ultra with a seven hour time limit. A virtual option is available and virtual runners can receive the same medal after verification.
A festive 12 km trail run around the woods of Dursley with a 6 km refreshments stop, optional fancy dress, chip timing and a finish at Dursley Rugby Club.
A pre Christmas anniversary timed run in Stroud on 13 December 2026 with flexible lap-based entry on a 3.28 mile canal route; distances range from 5 km to ultra and all finishers receive a bespoke medal and a memento.
Trail event in Nailsworth with a 10.46 km Rampage and a 3.18 km Dash, chip timed with finisher medals and a home cooked mince muffin.