Chipping
Trail Running Calendar near Chipping 2026-2027
Explore the top trail runs near Chipping for 2026-2027! We've gathered 102 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A 30 mile out and back trail ultra along the River Stort with checkpoints every 5 miles, enforced halfway and overall cut offs, electronic timing and finishers medals.
A 10 km night-time self-navigation trail around Thaxted from The Maypole, open to walkers and runners; entry fees include a drinks voucher and support John Webb’s Windmill restoration.
A single loop 50K trail across the Chilterns from Berkhamsted with 800 m ascent, three staffed checkpoints and a 9 hour cutoff on 31 October 2026.
A Halloween themed 6.66 km trail run in Chelmsford on 31 October 2026 with GPX/Strava route support, fancy dress prizes and a brewery finish offering a medal, drink and crisps.
An evening timed run at Riverside Park in St Neots on Halloween offering laps of a 5.3 km out and back course. Head torches are compulsory and all participants receive a finishers medal, with distances from one lap to ultra.
November 2026
Two days of marathon and half marathon races around Caldecotte Lake in Milton Keynes on 6 and 7 November 2026, with multi-lap clockwise courses, on-course water and toilets, enforced time limits, and bespoke finisher medals.
A November muddy obstacle event in Brentwood Essex with 6 km, 12 km and 24 km plus options across farmland, woods and lakes featuring 40 to 200 plus obstacles.
Experience a scenic trail run through the Bedfordshire countryside with a choice of a half marathon or metric half marathon along the Grand Union Canal and woodland paths.
Experience the longest established trail race in Essex with a self navigated course of 6 or 16 miles starting from a traditional pub in Chelmsford.
An evening 5 km charity trail run in Writtle on 11 November 2026 that donates £2 per entry to Whizz Kidz, with a self guided route and a pub finish.
A three day 84 mile ultra along the Ridgeway from Buckinghamshire to Wiltshire with overnight stays in Watlington and Didcot and full or single day entry options.
Countryside walking and running event from Barton le Clay with 12, 18 and 26 mile routes, checkpoints, mapped routes and refreshments included.
A lap-based timed run at Grafham Water as part of Phoenix Running's Elements Series. Laps are 5.3 km on mainly tarmac paths with distance options from 5 km to ultra and finisher medals for participants.
A half-day 10 km trail run in the Chiltern Hills followed by a private Tring Brewery tour with a tasting and a beer option.
A mostly off road 15k at Trifarm, Boreham, run on public footpaths and bridleways with on-site parking, water refill points and manual timing.
A timed, lapped Cakeathon at Mowsbury Park on 22 November 2026 offering flexible starts, a flat 5.3 km lap, distances from 5 km to ultra, and a seven hour limit.