Trail Running calendar near Chesham 2025-2026

The Chiltern Ridge Winter 50K will take place in Berkhamsted on Saturday 31 October 2026.

Run across the sands of West Wittering at the Witterings Beach Run this November, with 5 km, 10 km and 15 km options and canicross entries. Enjoy coastal views, chip timing and a finisher medal on a plastic free, dog friendly course.

Run Wendover Woods on challenging, hilly forest trails with marathon, half marathon, 10k and junior distances across mixed terrain. Enjoy onsite facilities like a cafe and plenty of parking plus bespoke medals and free race photos.

The Enigma Fireworks will take place in Caldecotte from Friday 6 November 2026 to Saturday 7 November 2026. You can run between 21 and 42 kilometers.

Run the rolling South Downs from Goodwood Racecourse this November, with 12km, 19km or 21km trail options. Tackle chalk tracks, forest trails and big views, enjoy on course support, chip timing and a finisher medal, and dogs are welcome.

Run the Remembrance Run 2026 South along the River Thames at Wraysbury in a reflective 7 hour lap challenge where you pick your distance. A two minute silence adjusts official times and finishers of 3 km or more earn medals.

Run under the stars through the rolling Chiltern Hills at Stonor Park in November with three waymarked trail options from 7 to 17 km. Expect a fully marked, timed night race; bring a headtorch and enjoy a finishers medal and event atmospher..

Run the Maverick Oxfordshire Trail at historic Stonor Park in the Chilterns AONB with 7 km, 13 km or 22 km routes through deer filled woods and under soaring red kites. Expect steep climbs, wild views and fully marked, timed trails.

Run from Alexandra Gardens in Windsor along flat, fast off road trails through parkland and woodland. Choose 10K or half marathon with chip timing, free photos and an event village serving food and giveaways.

Join the H&T Running Remembrance Sunday race in Brightlingsea for a moving pre race Last Post and two minutes silence. Tackle an undulating traffic free looped trail with half and full marathon options and friendly aid stations.

Remembrance Run at Wraysbury on the Thames is a timed 7 hour challenge where you choose any distance from 3 km to ultra. Scenic signed laps, aid stations with vegan options, a finisher medal and a two minute silence at 11:00.

Explore ancient woodland and open heath in the New Forest with 10 km, 17 km or 22 km trail options. Enjoy waymarked gravel paths, on course support and a finisher medal, and note water stations are plastic free so bring a reusable cup.

Run the North Chilterns 50K, a scenic trail ultramarathon from Putteridge Bury over Warden, Barton and Pegsdon Hills with sweeping views. Limited to 250 runners, this supported 50 km course is a rewarding late autumn challenge.

Join a guided 10km trail run around the scenic Devil's Punchbowl in Hindhead, with climbs and a summit pause to soak up the view. Enjoy sunset sessions or headtorch night runs led by an experienced trail coach in a friendly group.

Explore 30 miles of the Serpent Trail from Haslemere in a hilly, scenic group run through woodland, heath and views across the South Downs. Led by an experienced guide, this non race suits runners ready for long trail miles.

Join a guided Box Hill Vertical KM group run near Dorking for a tough 12.5 mile route with about 1000 m of climb through woods, heath and open fields. Enjoy expert guidance, technical terrain and a social finish.

Take on the new winter St Edmund Way Ultra on 5 December 2026, an 80 miles route through Essex, Suffolk and Norfolk. Remote trails, checkpoints and live public tracking make this a true day and night test of endurance.

Run the Sussex Downs Trail Run at Plumpton Racecourse for stunning South Downs and sea views across 9, 12 or 22 km routes. Expect rolling trails, friendly marshals, chip timing and a finisher medal for a rewarding winter trail experience.