Brentwood
Trail Running Calendar near Brentwood 2026-2027
Explore the top trail runs near Brentwood for 2026-2027! We've gathered 91 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A 10 km narrative night time trail around Thaxted, self navigated and timed, starting and finishing at The Maypole with proceeds to John Webb's Windmill.
A Halloween brewery trail run in Chelmsford with a devilish 6.66 km route, fancy dress rules, a finishers medal and limited places.
November 2026
An after dark multi terrain 10 km and 5 km run in Leigh on Sea on 1 Nov 2026 with chip timing, themed medals and support for local charities.
Muddy obstacle runs in Brentwood, Essex offering 6 km, 12 km and 24 km plus options across farmland, woods and lakes with dozens of natural and man made obstacles.
A self-navigation trail race on paths, tracks and country lanes with approx 16 and 6 mile routes and a different course each year.
Second Sunday 5 on 8 November 2026 at Richardson Evans Memorial Fields in Wimbledon Common is an informal two lap event organised by Thames Hare & Hounds.
Torchlit 5 km charity trail on 11 Nov 2026, supporting Whizz Kidz with a countryside route and a pub finish; places are limited.
Trifarm 15k trail run on 21 Nov 2026 at Trifarm, Boreham: 95%+ off road on public footpaths and bridleways with on site parking, water stations and manual timing.
A Half Marathon and a 10k on Wimbledon Common in London supporting Beder, with a trail marked course, course marshals and an event village offering food, drink and partner goodies.
December 2026
Essex Vets XC Championships in Epping Forest on 12 December 2026 features a single 8km course with veteran races and an £8 entry fee.
A hilly five mile trail race in Lesnes Abbey Woods on 13 December 2026 in memory of Ray Marshall, with manual timing and a 90 minute cut off.
A festive, informal two-lap Second Sunday 5 on 13 December 2026 at Richardson Evans Memorial Fields, Putney Vale.
An evening self navigation trail of about 6 miles from The Compasses in Littley Green with a secret destination, cryptic clue bonuses, refreshments and entry vouchers.
A social 12k run on 19 December 2026 with a GPX/Strava route, brewery and finish bar drink tokens, festive medals and a post-run rum option.
A 50 km trail ultra along the North Downs Way from Detling to Wye with about 1,000 m of ascent, three checkpoints and mandatory kit requirements. The route passes Boxley Warren, Thurnham Castle, Lenham Cross and the Wye Downs.
20 Dec 2026 at Abberton Reservoir Visitors Centre: repeat just over 5 km laps in a timed up to six hour challenge, with medals and proceeds to Essex Wildlife Trust.
Navigate an 11 mile circular trail between Maldon and Mundon using written instructions on a course that is 95 percent off road.
A winter trail 10k at Trifarm in Boreham on 27 Dec 2026, mostly off road on public footpaths and bridleways and serving as the final race of a four-round series.
A looped trail event in Crystal Palace Park where runners complete 2.65 km laps within a 7 hour time limit. Distances range from 5 km to ultra and all participants receive a finishers' medal.
January 2027
A narrative trail marathon around Danbury with 95% off-road terrain, three checkpoints, finishers' medal and hot food, based at East Hanningfield Village Hall.