Trail Running calendar near Chiltern Hills 2026-2027

A tenth anniversary five mile chip timed trail and Canicross across the Upper Wreake valley, with Hoby & District village hall as HQ and commemorative wooden medals for all finishers.

Wild Run Cotswolds showcases rugged off road trails on a private estate with fully marked routes, chip timing and a family friendly supporter zone. Entries are limited to 600; choose 10K, half, marathon or the six hour 360 challenge.

Riverside out and back races along the Thames Path from Petersham & Ham Sea Scouts, offering 10 km, half marathon and marathon distances on a flat, well marked trail shared with the public.

Wild Run Oxford is planned for 4 October 2026 (TBC) on Oxford's nearby trails, with a 10K and a Half Marathon on mixed smooth and rugged terrain; the event is licensed by the Trail Running Association and UK Athletics.

A challenge event in and around Marlow on 4 October 2026 offering 25 km, 40 km and 50 km routes through the Chilterns, organised by LDWA Thames Valley with checkpoint refreshments, a finish meal and limited entry.

A guided 30 mile trail run from St Martha's, Guildford along the North Downs Way via Box Hill and Denbies Wine Estate. Group-paced with coaching support; participants should have completed long training runs and carry suitable kit.

Looped 50 km, 25 km and 10 km routes from a Maidstone basecamp travel the North Downs Way, the River Medway and past Leeds Castle with covered rest stops, GPS tracking, camping and finisher medal and t shirt.

Tackle chalk climbs, ridgelines and singletrack at Beat Box Hill, with distances from 21k to 50k and charity places. Marked routes, marshals, chip timing and a finish village with food and a themed medal await.

Tackle 55 km through the Forest of Dean, from ridges and dense woodland to the River Wye and Symonds Yat viewpoint. Technical single track and riverside sections offer scenic challenge and there is a canicross category.

Choose a scenic 10k or shorter 5k through the Chiltern Hills around Frieth, combining woodland paths and country roads. Expect rolling climbs and panoramic views for a rewarding, hilly challenge for road and trail runners.

A circular 13.1 mile trail race in Thetford Forest around High Lodge held in October. The traffic free, multi terrain course is manually timed with cupless water provision, on the day number collection, medals and trophies for top finishers..

Enjoy a scenic 10k through the woodlands of Limpsfield Common and High Chart in Oxted Surrey, with rolling climbs and a downhill finish. Single lap route suits trail runners seeking a challenging rewarding outing.

Join the Grafham Water Trail Races on 11 October 2026 with 10k and half marathon routes from Marlow Park around the reservoir on fully marked trails. Enjoy scenic water views, marshalled support and a finishers medal for all.

Run and support local schools at the FOOBS Trail and Fun Runs in Old Basing on 11 October 2026. Scenic community trails offer a 2K family fun run or chip timed 6K and 10K routes, with post run treats and plenty of local support.

A 100 mile trail race from Goring and Streatley using Thames Path and the Ridgeway, featuring four 25 mile out and back legs, 16 aid stations and a 28 hour cutoff; entrants must meet a 50 mile qualifier and be 20 or older.

An annual 25 km or 50 km countryside challenge around Kent, Surrey and Sussex with written route instructions, checkpoints and food included; participants aim to complete their chosen distance within ten hours.

Blaze the Biblins on 18 October 2026 is a scenic 10k trail race through ancient woods and riverbanks near Ross on Wye. Expect technical single track, climbs including the notorious Demon hill, and a lively village finish.

Roughly 12K trail run on bridle paths and the Imber Range near the Westbury White Horse on 18 October 2026. Limited to 200 places so book early for a bespoke finisher medal and category prizes.

Keynsham Dandy is an off-road race on Sunday 18 October 2026 around Keynsham. The roughly 12.5 mile course starts at The New Inn and includes the revived Compton Dando route with a stream feature.

Woodland half marathon and 10k at Bedgebury National Pinetum & Forest on 18 October 2026, with downloadable route maps, a bespoke medal, free photos and limited free parking.