Trail Running calendar near Cheltenham 2026-2027

A guided 30 km trail run in the Chiltern Hills from Tring, with checkpoints, trail technique instruction, a finisher’s medal and Trees not Tees certificate.

A Pretty Muddy 5k obstacle course at Braunstone Park on 15 May 2027 combining grass and path with climbs, crawls and slides. Waves start every 15 minutes, participants must be 13 or older and there is a minimum fundraising target of £50.

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.

A 50-mile point-to-point ultramarathon on the North Downs Way from Farnham to Knockholt Pound with about 5,600 ft of ascent, six aid stations, medical support and a 13 hour cutoff.

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.

A single-lap *50 km* multi terrain ultra in Maidenhead on May 22 2027, mainly off road along the Thames Path, Jubilee River and the Green Way. Four aid stations, chip timing, live tracking and on-course nutrition support.

Point to point trail in Surrey offering 62K, 41K and 20K routes plus 2 and 3 leg relays with marked courses, chip timing and an event village with food and partner goodies.

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.

Northampton hosts 5 km, 10 km and junior races on Sunday 23 May 2027 at Sixfields Stadium. The start and finish are inside the stadium and the course continues on closed roads around Northampton.

Enjoy an undulating 10km trail run through Marlow's woodlands and Thames towpath, finishing with a commemorative medal and a refreshing drink from Rebellion Brewery.

A guided trail half marathon around the Surrey Hills, about 13 miles from St Martha's Hill in Guildford, following parts of the North Downs Way and notable viewpoints. The run is social in format with a guided pace and evening options.

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 (50, 26, 16 miles) follow the final sections of the Heart of Wales Line, finishing at the Shropshire Hills Discovery Centre, with baggage transfer and varying checkpoint support by distance.