Trail Running calendar near Chepstow 2026-2027

We have found 479 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

An eight hour timed event near Exmouth with 5.3 km out and back laps on a tarmac route along an old train line. Flexible on day starts, a mix of medals for finishers and a maximum of 75 entrants.

A short but steep fell race near Llanfoist and Abergavenny covering 5.7 km with 485 m of ascent. The course is mostly unmarked, needs basic navigation and can be affected by poor weather.

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.

An 8 hour timed road event on 29 November 2026 near Littleham, Exmouth, with 5.3 km laps on a tarmac out and back course along a disused train line. The TUGG system allows flexible starts and medals are awarded for laps completed.

The final race of the 2026 RTT Series takes place in Afan Forest with separate 5 km and 10 km routes from Bryn Bettws Lodge. The event features chip timing, finisher medals, marked and marshalled routes and water stations.

Trail races at Mapledurham Estate offering 10K, 10 Mile and Half Marathon routes over muddy paths and woodland, with on-course water, finish refreshments and race amenities included.

A late November trail race through 600 acres of dense woodland at Charborough Estate offering a 10 km loop, a 21 km double loop and a relay for two runners. Expect rough rooted trails, one aid station and a marked course.

A time trial from Little Stretton to the Stiperstones with on the day entry and a finish to start bus. Navigational skills are required and entry fees are £8 per person with a reduced junior rate.

Ras Y Mast is a club organised running event held at Blaenwern Holiday Centre in Llanybydder, Ceredigion, featuring a mixed surface course of 6.5 miles and separate junior and senior races.

A lap based road event at Rhydycar, Merthyr Tydfil, on a 5.3 km AUKCM certified tarmac circuit along the Taff Trail. Runners choose how many laps to complete within a seven hour limit and can opt for a no medal entry.

December 2026

Coastal 10 Mile and 10k runs from Hengistbury Head along Bournemouth seafront and Boscombe Pier, with largely flat, traffic-free paths, chip timing, water stations and a finisher's medal.

Trail races of 10K, half, marathon and ultra run from Swanage along the Jurassic Coast Path on 5 December 2026, on trail and grass terrain with significant ascent; online check-in and mandatory safety briefing are required.

A 14.5 km fell race near Church Stretton with about 793 m of ascent, marked and marshalled except for a section on The Lawley. Entry is online with 180 places and full FRA kit is mandatory.

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 vir..

A winter trail running festival at Holmesly Campsite in the New Forest on 6 December 2026, offering 15 km, 30 km, marathon and 50 km one lap off‑road courses with marked routes, bag drop and mandatory kit requirements.

A festive trail event at Chasewater Country Park featuring 10k, 5k and a junior run, raising funds for Shelter, with bespoke medals, photos, prizes and onsite parking.

A festive 5 km off road Santa Dash at Tinkley Gate raising funds for Allsorts. Costumes, dogs on short leads and a 2.5 km one lap option for younger participants make this a family friendly event.

A festive trail running event at Moors Valley Country Park on 6 December 2026, offering a 2 km fun run for children plus 5 km and 10 km trail races; on-site parking is available for £5 and entry fees range from £12 to £26.

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.

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