Maidstone
Trail Running Calendar near Maidstone 2026-2027
Explore the top trail runs near Maidstone for 2026-2027! We've gathered 61 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Off road marathon and half marathon south of Canterbury with live tracking, checkpoints, mandatory kit lists, event HQ facilities, and a charity donation from entries.
Halloween themed night trail at Langdon Nature Discovery Park with a 5k for ages 12 and over and a free 800m Little Monsters children's trail.
An overnight self supported 50 km ultra from East Grinstead to Brighton on 30 to 31 October 2026, in person event with tickets at £14.46 and no refunds.
November 2026
An after dark 10 km and 5 km multi terrain run in Leigh on Sea with chip timing, mandatory headtorches, sustainable finisher medals and local charity support.
Nuclear Fallout at Nuclear Essex hosts winter muddy obstacle races over 6 km, 12 km or a 24 km endurance format with dozens to hundreds of obstacles across farmland and woodland.
A 6.66 mile woodland trail run at Kings Wood near Ashford featuring muddy, hilly and technical sections, limited to 200 runners and organised by Ashford Tri Club.
Day 1 of a five-day Road Runner series at Gravesend Cyclopark on 18 November 2026, using a certified 5.25-mile out-and-back course. Seven-hour timed events, large daily-colour medals, aid station, and both attended and virtual entry options.
A rolling 10-mile loop around Ashdown Forest across heathland, woodland and sandy tracks with varied climbs and a GPX route for a social trail run.
Scenic 8.5 km loop around Northiam with over 70% off road trail, limited to 60 entrants, prizes for first male and female and tea and cake after at the village hall.
Trail event near Chelmsford on 29 Nov 2026 with two unsigned narrative routes of about 8.6 and 5.5 miles; proceeds support Centre Point Charity.
December 2026
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 marked 4 mile trail run around Pett on 19 December 2026 with a finisher medal, prizes and tea and cake afterwards.
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.
A charity off-road three mile run in Saltwood on 26 December 2026 that usually attracts over 1,000 entrants, with medals for all finishers and several entry options.
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.
A 7.5 km trail loop around Westfield with over 80% off-road surfaces, a marked and marshalled course, hall facilities and a 60-runner entry limit.
A 10 mile cross country race in Hainault Forest over three laps on tracks and grassland, with on-the-day entries, a two hour cut-off and prizes for men, women and veterans.
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.
A narrative trail marathon around Danbury with 95% off-road terrain, three checkpoints, finishers' medal and hot food, based at East Hanningfield Village Hall.