Trail Running calendar near Chepstow 2026-2027

We have found 335 Trailruns within 80 miles of Chepstow. See below where and when you can find the races.

Run through ancient woodland and heathland in the New Forest near Brockenhurst, where free roaming ponies, horses and deer may appear. Choose the half marathon or a shorter route and enjoy a medal, finisher's gift and drink.

Trail Revolution stages three waymarked trail races at Margam Park on woodland paths, offering 5 km, 10 km and half marathon distances with checkpoints, GPS routes and parking included in the entry.

A 10 km multi terrain trail run around Beckbury, Shropshire, featuring the Badgers Bite Hill, marshalled and signposted with a halfway drinks station and a finisher medal.

A night trail run from Corfe Castle with 15 km, 11 km and 5 km routes across muddy heath and woodland, one outpost on the long route, no dogs and no headphones permitted.

An eight hour timed road event on 28 November 2026 near Littleham, Exmouth, with 5.3 km laps on a measured tarmac out and back route along an old disused train line. Entrants must be 18 or older and the field is limited to 75.

An eight hour timed road event near Exmouth on an accurately measured tarmac out and back course along a disused train line. Flexible arrival on the day, lap length is 5.3 km and medals come from a mixed set.

December 2026

Choose 10 Mile or 10K starting at Hengistbury Head and run Bournemouth seafront via Boscombe Pier on largely flat, traffic free paths with sea views. Chip timed and marshalled, the event offers water, post race treats and a medal for finish..

Experience the dramatic Jurassic Coast around Swanage on 6 December 2025 with wet, challenging trail and coastal climbs from 10K to ultra. Fully marked course with electronic timing and finishers medals, but entries are full.

Take on the Cardington Cracker, a 9 mile fell race near Church Stretton with 793 m of climb and breathtaking Border views. Pre entry only and limited parking mean early sign up is essential for this rugged, rewarding test.

Join The Partridge in a Pear Tree at Pengethley Manor, Ross on Wye for a scenic offroad race through vineyards and rolling hills. Choose 5k, 10k, half marathon, marathon or ultra, walkers welcome and virtual entries available.

New Forest Xmas Trails offers festive trail races from Holmesly Campsite in the New Forest. Distances range from 15 km to a 50 km ultramarathon on fully marked heath and woodland trails; opt to plant a tree instead of a medal.

Join the Chasewater Christmas Pudding Dash at Chasewater Country Park for festive fun with 10k, 5k and a Junior Run on mostly flat reservoir trails. Enjoy medals, photos and prizes including best dressed fancy dress while supporting Shelter..

Don your Santa suit and join 250 Santas and elves for a festive community 5 km at Tinkley Gate National Trust in Woodchester on 6 December 2026. Proceeds support Allsorts charity helping children and young people with additional needs.

Celebrate the season at 2 Turtle Doves at Pengethley Manor on 7 Dec, an offroad 2.5 km loop through vineyards and rolling hills with distances from 5k to ultra. Runners and walkers are welcome for a friendly, festive challenge.

Choose your distance from 5k to ultra and tackle scenic off road laps through Pengethley Manor's vineyards, with a testing hill on every circuit. Walkers and runners welcome at this one day stop in a 12 day Christmas race series.

Run the 4 Calling Birds at Pengethley Manor, part of a 12 day Christmas series, with distances from 5k to ultra and seven hours to complete. The off road loop climbs a hill and winds through two vineyards, welcoming runners and walkers.

Join the 5 Golden Rings Run at Pengethley Manor, Ross on Wye for a festive offroad challenge through vineyard trails with a hill each lap. Choose 5k up to ultra on a walker friendly course with medals and virtual entries.

Tackle the 6 Geese a laying Run at scenic Pengethley Manor, a tough offroad loop through vineyards with a hill each lap. Choose 5k, 10k, half marathon, marathon or ultra, on site or virtual, open to runners and walkers aged 18 and over.

Run the 7 Swans a Swimming on 12 December 2026 at Pengethley Manor, Ross on Wye for a scenic offroad loop through manor grounds and vineyards. Distances range from 5k to ultra and the event welcomes walkers and runners.

Celtic Trail Races bring three winter trail distances in South Wales, from flowing single track to steep climbs, with views over the Brecon Beacons. Courses are waymarked and finish at Dare Valley Country Park with checkpoint support.