Trail Running calendar near Chepstow 2026-2027

Two day obstacle race weekend in Henley on Thames featuring Sprint, Super, Beast and kids races across historic town and riverside terrain.

A measured 50 km route from Telford Town Park to Shrewsbury that passes historic sites such as Ironbridge, Buildwas Abbey and Wroxeter Roman City. The event features chip timing, five nutrition stations and a bespoke finish medal.

Multi-distance trail event on the Dorset Jurassic Coast on 15-16 May 2027 with full 100 km and shorter options, supported rest stops, GPS tracking, camping, and finish in Bridport.

A muddy 5k obstacle course through Singleton Park with mixed terrain, staggered waves, an age limit of 13+, and on-site facilities including toilets and refreshments.

Several distances are available: 5k, 10k and 20k routes around Deddington. The event is open to all ages and organised to raise funds for Deddington Primary School PTA, Deddington PFSU and the Firefighters Charity via Deddington Fire Statio..

A 10k trail run at Symonds Yat with riverside views and a notable final one kilometre climb. The mostly off road course includes long gravel firetracks and on site coffee and hot food.

A weekend of waymarked trail runs and walks at Mapledurham House near Reading, featuring ultras, a half marathon and supported marathon-length walks.

Trail running from Sudeley Castle through the northern Cotswolds, with five routes from 7 km to 50 km across bridleways, woodland and open ridge lines.

An untimed inflatable obstacle run at North Somerset Showground on 22 May 2027 offering 2.5 km laps with options up to 15 km and family-friendly entries.

Margam Wild Trail Runs at Margam Country Park on 23 May 2027 offers 5 km, 10 km and half marathon trail routes, is canicross friendly, uses live chip timing, and provides medals and post-race refreshments.

A 5 km obstacle event at War Memorial Park on 23 May 2027 where participants climb, crawl and slide across mixed grass and path terrain; entrants must be 13 or older and a minimum fundraising target of £50 applies.

A multi-stage event at Dare Valley Country Park where runners complete five Pure distances within 24 hours, with separate and combined results. Distances include 5k, 10k, 50k, half marathon and marathon.

A fully supported trail running event in May 2027 along the way-marked Heart of Wales Line Trail from Llandrindod Wells to Craven Arms, offered in **50 miles**, **26 miles**, and **16 miles** distances.

Three trail races of 50, 26 and 16 miles along the final sections of the Heart of Wales Line finishing at the Shropshire Hills Discovery Centre.

The Pretty Muddy 5 km obstacle course at Baiter Park, Poole on 29 May 2027 runs across grass and tarmac with staggered wave starts every 15 minutes. Participants must be 13 or older and there is a minimum fundraising target.

A 60 km point-to-point ultramarathon from Ivinghoe Beacon to Ridgeway View Campsite along the Ridgeway National Trail, fully marked with four aid stations.

A 24 hour off road trail event on 5 mile loops with solo, pairs and team categories, onsite campsite, parking, caterers and illuminated night routes.

A family sports festival in Salisbury featuring multi terrain races, five a side football, live music and fundraising for prostate cancer on 30 May 2027.

A 24 hour relay at Wasing Park, Reading where Solos, Pairs and Teams run an undulating 8 km trail lap with camping and an on-site event village.

The VOGUM 2027 is an in-person running event in Porthcawl, United Kingdom, organised by Stable Adventures on 5 June 2027; entries are listed as sold out.