Trail Running calendar near Chepstow 2025-2026

The Medal Mix Challenge Day 2, organized by Running Events Devon, takes place near Capel Lane, Littleham, Exmouth on Sunday, 30th November 2025. This 7-hour timed event features an accurately measured 5.3 km out-and-back course on a scenic,..

Explore Afan Forest on hand picked trails with 5K and 10K options at the RTT Afan Forest run. Fully marked and marshalled courses, chip timing and a finisher medal make this a rewarding, well organised trail day for all abilities.

Take on the Winter Bumble Bimble 5 mile trail run from the Park Gate Inn in Bromsgrove on Sunday 30 November 2025. Entries are limited to 300 and all finishers get a medal as you tackle woodland, rolling fields and muddy scenic trails.

Join the Marton Mile on Sunday 30 November 2025 for a relaxed one mile walk jog or run along the flat traffic free Lias Line Greenway near Marton. This family and dog friendly community fundraiser supports Shelter and welcomes all paces wit..

Run a scenic, traffic free 6.5 mile (about 10K) lap of Croome Park with a big hill to start and finish. Trail shoes are recommended and all finishers receive medals and goody bags.

Night orienteering in Brockenhurst: a 60 minute score event in the New Forest. Visit as many controls as you can for points using SIAC timing and waterproof maps, and bring high visibility clothing and lights for after dark navigation.

Take on the dramatic Jurassic Coast path in Swanage with options from 10K to a 32 mile ultra on 6 December 2025. Expect challenging trails, full course marking and timing, and a finishers medal to celebrate your effort.

Serious Santa trail races serve up rugged, scenic runs in the Black Mountains from Cwmdu Village Hall with Half Marathon, Ten Mile and 14 km options. Expect technical trails, festive vibes and handmade finisher trophies.

Winter trail runs in the Brecon Beacons from Cwmdu Hall, across rocky ridges, moorland and single track trails in multiple distances. Well stocked checkpoints, full course support, mulled wine and mince pie, plus camping and dog friendly.

Take on 50 miles of winter trails around Telford and Shropshire, taking in Ironbridge and the Wrekin at the Telford T50 Trail Run. Clear waymarking, well stocked aid stations and friendly marshals make for a rewarding endurance day.

Brave the winter trails of Salisbury Plain with undulating terrain, steep climbs and compact tracks across historic military land. Half and marathon options come with marked routes, aid stations and finisher medals, so bring trail shoes.

Enjoy the Otterton Reindeer Run on 6 December with a festive 3 km fun run or a 10 km multi terrain through the Otter Valley. Family friendly, fancy dress prizes and village refreshments with proceeds aiding local projects.

Explore the New Forest with Wessex Orienteering from Bolderwood Car Park, tackling technical woodland courses from a challenging Blue to a 60 minute Score challenge. Entry and parking are limited so book early and car share if you can.

Tackle the hills at the 36th Cardington Cracker on 7 December 2025 near Church Stretton. This 14.5 km FRA AM fell race climbs 793 m across rough winter terrain so advance entry is advised.

Join the New Forest Xmas Trails on 7 December 2025 for a festive run through heath and woodland in the New Forest. Fully marked single lap courses from 15km to 50km start at Holmesly Campsite and you can plant a tree instead of a medal.

Celebrate the season at the Chasewater Christmas Pudding Dash at Chasewater Country Park, a festive 10k, 5k and junior race around the reservoir on mostly flat trails. Enjoy medals, photos and fancy dress prizes while supporting Shelter.

Join the inaugural Allsorts Tinkley Gate Santa Dash for a festive family friendly 5 km trail run at Woodchester, with costumes and a post race cafe. Dress as Santa or an elf to support local charity Allsorts; dogs on short leashes welcome.

Join Partridge in a Pear Tree at Pengethley Manor on 7 December 2025, part of the festive 12 Days of Christmas series with distances from 5k to Ultra and a unique medal. Run or walk a scenic offroad loop through manor grounds, vineyards and..

Navigate the sand dune maze of Braunton Burrows South at a scenic orienteering event on Sunday 7 December, part of the South West Orienteering League. Multiple courses for all abilities promise coastal views across the Taw estuary and Saunt..

Take on the 2 Turtle Doves Run at Pengethley Manor on 8 December 2025, choosing distances from 5k to ultra with a 7 hour limit. Offroad laps wind through vineyards and a testing hill, walkers and runners both welcome.