Gillingham
Trail Running Calendar near Gillingham 2026-2027
Explore the top trail runs near Gillingham for 2026-2027! We've gathered 76 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Timed, self supported loop around Canvey Island starting and finishing at Waterside Farm Leisure Centre with a pub stop at 10 km and a four hour cutoff.
Trail marathon and half marathon near Canterbury through Kentish countryside; marathon requires navigation and both races use CCCU Sports Centre as HQ.
A countryside walking event from Blackmore with a 26 mile figure of eight route and an 18 mile option, forming part of the Essex and Herts Triple Challenge.
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.
November 2026
An after dark multi terrain 10 km and 5 km event in Leigh on Sea with chip timing, mandatory headtorches and sustainably sourced finishers medals.
A November muddy obstacle event in Essex offering 6 km, 12 km and 24 km+ courses with natural and man‑made obstacles including a Deathslide and zip wire.
A mostly off road 15k at Trifarm, Boreham, run on public footpaths and bridleways with on-site parking, water refill points and manual timing.
December 2026
A social 12k at Chelmsford Brewery with a GPX and Strava route, checkpoint drinks and Christmas medals, plus encouraged fancy dress.
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.
Final round of the four-event Trifarm Winter series: a mainly off-road 10 km on public footpaths and bridleways at Trifarm in Boreham on 27 December 2026.
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
An annual New Year five mile cross country in Penshurst village over rolling hills and woodland trails. Open to ages 10 and above with entry fees supporting Hospice in the Weald and awards across junior, local and canicross categories.
Running at Bewl Water on 10 January 2027 with 10k, 5k and a junior run on multi terrain routes beside the reservoir; maps and GPX files are provided.
February 2027
Trail races of 10 Mile, 5 Mile and a junior run take place in Bedgebury National Pinetum & Forest on 7 February 2027. The undulating multi terrain courses can be muddy after wet weather and include a bespoke medal and free photos.
A timed lap event in Crystal Palace Park on 21 February 2027 where runners complete 2.65 km laps to reach distances from 5 km to ultra, with a seven hour limit and a finishers' memento for all participants.
A 42-mile trail race from Chipping Ongar to the ancient Chapel of St Peter-on-the-Wall, following an old pilgrimage route through rural Essex. Mostly off-road and often muddy, the route is waymarked with GPX support, four outdoor checkpoints and mand..
A single lap undulating 10k trail race at Hadleigh Country Park with steep hills, deep mud, technical terrain and mandatory trail shoes.
March 2027
May 2027
A four leg stage trail relay along the Roach Valley Way covering 23 miles in total. Teams of four navigate by maps and way markers while proceeds support Havens Hospices.