Trail Running calendar near Chiltern Hills 2026-2027
We have found 486 Trailruns within 80 miles of Chiltern Hills. See below where and when you can find the races.
Distance (km)
Articles
Belgian Ultrarunner Karel Sabbe's Record-Breaking Pacific Crest Trail Run Showcased in New YouTube Documentary
Explore Karel Sabbe's record-breaking Pacific Crest Trail run in a riveting documentary. Jour..
Trail Running: How it Can Help Reduce Stress and Anxiety
Trail running is an effective way to reduce stress, anxiety, and improve physical and mental he..
Trail Running vs. Road Running: Which One Is Right For You?
When it comes to running, there are two primary options to choose from: trail running and road..
Halloween 7in7 at Pengethley Manor, Ross on Wye offers seven consecutive days of off road laps through vineyards and a hill, with distances from 5k to ultra. Walk or run any day or go virtual and collect seven themed medals.
Join the Witches Whisk at Pengethley Manor for a spooky Halloween trail across 2.5 km laps through vineyards and rolling offroad terrain. Pick 5k to ultra distances, ideal for runners or walkers after a fun seasonal challenge.
Celebrate Halloween at Pengethley Manor with the Scary Scamper, an offroad multi lap course winding through vineyards and hill sections on the manor grounds. Distances from 5k to ultra welcome runners and walkers with a 7 hour time limit.
The Creepy Crawl is an offroad run through Pengethley Manor's vineyards with a hill each lap, offering distances from 5k to ultra and open to all. Pick your distance, finish within 7 hours and earn an onsite or virtual medal.
Join the Ghostly Gallop at Pengethley Manor on 22 October 2026 for a spooky offroad challenge through vineyards and rolling hills. Choose distances from 5k to ultra with in person or virtual entries and Halloween themed medals.
Join the Petrified Pootle, a Halloween off road run at Pengethley Manor offering distances from 5k to ultra for walkers and runners. Tackle hilly vineyard trails, soak up the spooky vibe and earn a finisher medal or run virtually.
A point-to-point ultra along the Thames Path and Ridgeway covering around 47 miles from Iffley to Henley-on-Thames, with mixed riverside trails, five aid stations, GPS tracking and mandatory kit requirements.
UTMB Index
Join the Spooky Sprint at Pengethley Manor, Ross on Wye on 24 October 2026 for a tough offroad Halloween race through two vineyards. Choose on course or virtual options from 5k up to ultra and enjoy a scenic, challenging looped course.
A 30-mile out-and-back ultra along the River Stort and Lee navigations, mostly flat grassy trail with checkpoints about every 5 miles and four- and eight-hour cut-offs. Based at Hockerill Sports and Social Club with medals and trophies for..
Join the Halloween Zombie Shuffle at Pengethley Manor on 25 October 2026 for off road fun through vineyards and hills. Choose a 5k to ultra, walk or run on a looped course with a 7 hour time limit and a virtual entry option.
Timed multi terrain loop at Ferry Meadows on 25 October 2026 with four hour and six hour options. Runners complete as many 5.3 km laps as they wish, with an aid station each lap and event or lucky dip medals available.
A 5 mile timed, self-navigated night trail on 30 October 2026, run mostly through forest and downland. Fancy dress is encouraged with trophies and a post-run dessert for winners, and a tail runner will sweep the course.
A single-loop 50K trail ultramarathon in the Chilterns on 31 October 2026, starting and finishing in Berkhamsted with marked navigation, three aid stations and a 9 hour time limit.
UTMB Index
Join a devilish 6.66 km Halloween trail at Brewery Fields, Great Baddow on 31 October, a fun fancy dress event rather than a race. Limited to 50 places, finishers get a medal, drink and costume prizes and a GPX route is provided.
November 2026
Trail races in Wendover Woods, Buckinghamshire offer marathon, half marathon, 10k and a junior 1k on hilly forest trails with mixed terrain, onsite facilities and event medals and photos; there is a six hour cutoff.
Tackle the Apocalypse Run, a rugged 10 mile trail through Stonehouse with a stiff opening climb and muddy, undulating terrain. Canicross runners welcome and all finishers get a medal for braving the off road challenge.
An out and back five mile running event in Market Harborough featuring a lit passage through the 422 m Oxendon Tunnel, with separate Night and Dawn runs, on-course first aid, finishers' medals and post-race refreshments.
Join Enigma Fireworks on 6 and 7 November 2026 for marathon and half marathon loops around scenic Caldecotte Lake. Enjoy waterside views, lap support and a bespoke finisher medal to light up your race season.