Trail Running calendar near Upper Woolhampton 2026-2027

An annual 25 km or 50 km challenge across Kent, Surrey and Sussex footpaths, navigated from written route directions with checkpoints, food included and a ten hour completion objective.

A guided 10 mile trail run in the Chilterns along canals, reservoirs and past Britain’s oldest post windmill, with a trail leader, technique instruction and a finisher’s medal included.

A roughly 12K off-road race on 18 October 2026 that follows bridle paths along the Imber Range and passes close to the Westbury White Horse, with limited places, age and equipment restrictions, and finishing medals for all.

Keynsham Dandy is an off-road race on 18 October 2026 organised by Town and Country Harriers; the roughly 12.5 mile course starts in Keynsham and includes the revived Compton Dando route with a stream, with Race HQ at The New Inn.

Woodland half marathon and 10k at Bedgebury National Pinetum in Kent on 18 October 2026, with traffic-free forest trails, downloadable GPX maps, medals, free photos and limited free parking.

An off‑road cross‑country race in Hardwick, Buckinghamshire, covering about 6 miles across varied terrain and water crossings. Entry is limited to 300 runners, with medals and category prizes including team awards.

The Blackdown Hill Challenge on 18 October 2026 is a trail running event from Fernhurst Recreation Ground to the Temple of the Winds, featuring a 866 ft climb and wide views. A shorter adult trail of about 4.5 km is also offered.

Trail runs of 10 km and 5 km around Blackpit Brewery on October 18 2026, using private multi terrain trails through woodlands and estate tracks. Entrants receive a medal, a pint cup and a free drink at the finish.

Seven consecutive offroad race days at Pengethley Manor from 19 to 25 October 2026 with a seven hour time limit each day and distances from 5k to ultra. Each day awards a unique Halloween themed medal and a virtual option is available.

An offroad Halloween race at Pengethley Manor offering 5k, 10k, half marathon, marathon and ultra distances with a seven hour time limit. In-person and virtual entries are available and paid verified finishes receive themed medals.

Part of a Halloween race series at Pengethley Manor, The Scary Scamper offers 5k, 10k, half, marathon and ultra options on a tough off road loop with a seven hour time limit and a virtual option worldwide.

Part of a Halloween series at Pengethley Manor, The Creepy Crawl offers 5k to ultra distances on an offroad, lap-based course with a seven hour time limit. Virtual entries and themed medals are available for paid participants.

A 5k night trail at Dunkertons Park in Cheltenham where runners use head torches to light the course. Open to ages 16 and over, with prizes for top three men and women and on-site refreshments and safety rules.

An offroad event at Pengethley Manor offering 5k, 10k, half, marathon and ultra distances with a seven hour time limit, on-course laps of 2.5k and themed medals; virtual participation and a charity entry option are available.

A Halloween series race at Pengethley Manor with 5k, 10k, half marathon, marathon and ultra options and a seven hour time limit. The offroad course runs inside the manor grounds and includes a hill and vineyard sections.

Beachy Head Marathon Weekend runs multiple trail distances from a 10k to an ultra near Bede's Prep School in BN20 7XL on 24/10/2026. Runners comment on clear signage, friendly marshals, stocked aid stations and hilly coastal terrain.

A point to point 47 miles ultra along the Thames Path and Ridgeway from Iffley to Henley-on-Thames, mostly on trails, with five aid stations, mandatory kit checks, baggage transfer and live GPS tracking.

A Halloween series event at Pengethley Manor offering 5k, 10k, half, marathon and ultra distances on a tough offroad course with vineyard laps. Entrants have seven hours to finish and virtual participation is available.

A 30 mile out and back ultra along the River Stort and Lee navigations on the Hertfordshire Essex border, mostly flat grassy and gravel trail with checkpoints every 5 miles, electronic timing, medals for finishers and trophies for top three..

A hip-hop themed coastal run at Milford on Sea with mixed terrain and coastal views. Runners choose distances from 5 km to ultra-marathon, completing 5.3 km out and back laps with an aid station and themed medal.