Trail Running calendar near Chiltern Hills 2026-2027

We have found 496 Trailruns within 80 miles of Chiltern Hills. See below where and when you can find the races.

A single stage non stop trail run of approximately 102 miles along the Cotswold Way from Chipping Campden to Bath. The route is very hilly with varied surfaces and includes live tracking, aid stations and medical support.

UTMB Index

Explore Kent's countryside on the Triple Trail Races, with 25 km, 50 km and 100 km options that thread the North Downs Way, Greensand Way and Weald Way past woodlands, orchards and Leeds Castle. Finish at Loddington Farm race village with f..

BigSky is the Air event in the Classic Element Trail Series at Hyde Common, New Forest, offering 18 miles, a marathon and a 50 km ultramarathon with marked routes, multiple aid stations and mandatory personal hydration.

Trail races around Clipston offer a half marathon and a 5 mile country run across bridleways, footpaths and minor roads. The course gains 237 m and all finishers receive a medal and homemade cake.

Run looped, technical trails through the New Forest from Avon Tyrrell, with a Grade I listed manor as a backdrop. Pick your distance on the day from 5K to ultra and earn a medal for completing one loop or more.

A marathon and half marathon along the Ouse Valley Way in Huntingdonshire on 20th September 2026, finishing in Earith. Both routes are very low elevation and run on grass, gravel and tarmac with route maps and GPX files available.

A looped trail event in the Chilterns with a 50 km main route plus 25 km and 10 km options. Henley Showground basecamp offers camping, catering, shuttle services, rest stops, medical cover and GPS tracking.

UTMB Index

A 10 mile trail race at Chilton Manor Farm with a one mile yew tree lined finish, mixed off-road terrain and views toward Winchester and the South Downs. Entry includes a sustainable finisher medal, timed results and water stations.

A seasonal running event at Bullbanks Farm near Colchester on 27 September 2026 offering 10K, 5K and a 1K family run. The course uses traffic free farm tracks with chip timing and an event village for families.

Run through ancient woodland in the Forest of Dean at the Autumn Half Marathon starting and finishing at Speech House. This scenic 13 mile trail on well marked tracks supports local charities and awards a medal to every finisher.

Trail runs at Salisbury Racecourse across marathon, half marathon and 10k routes through undulating downland, woodland and Martin Down Nature Reserve, with several archaeological features along the courses.

Volunteer run charity 10k and 3k in Grantchester on 27 September 2026 supporting Maggie's Centre Cambridge and ACT. Courses run on farmland with chip timing, medals for finishers and on site refreshments.

A ten mile traffic free trail race at Eridge Park on 27 September 2026 with steep climbs, muddy sections and varied scenery. Organised by Tunbridge Wells Harriers, finishers receive a memento plus cake and a pint.

Run as many 3.3 mile laps as you can in six hours around leafy Coombe Abbey Park, with mainly flat stone paths and a meadow section that may get muddy. Choose a medal or an eco friendly tree token and refuel at the on site cafe.

October 2026

Tackle 100 mile across the rolling South Downs, starting and finishing at Plumpton Racecourse. With 12,000 ft of ascent, scenic views and a 34 hour cutoff, this autumn single loop ultra is a true test.

UTMB Index

Run to the Sea Bournemouth is a scenic 50 km point to point ultra from Moors Valley to Hengistbury Head on 3 October 2026. Expect flat forest trails and seafront running, four feed stations, tracking and a bespoke medal.

Take on the Epping Forest 50 KM 2026, a scenic 50 km trail challenge through ancient woods on 3 October 2026. Enjoy varied terrain, fresh air and a memorable run just outside London.

Hit the trails at London EcoTrail 25 KM on 3 October 2026 in Epping's Bell Common. Enjoy a scenic 25 km route through woodlands and countryside, perfect for trail runners craving a nature filled challenge.

Run the Dark Downs under the stars on 3 October 2026 at Plumpton Racecourse in Lewes. Choose a 50 km or half marathon loop across rolling South Downs trails with reflective signage and marshals for a magical night race.

UTMB Index

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.