Maidstone
Trail Running Calendar near Maidstone 2026-2027
Explore the top trail runs near Maidstone for 2026-2027! We've gathered 63 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
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 on 7 November 2026 at Nuclear Essex offers 6 km, 12 km and 24 km plus muddy obstacle courses across farmland, woods and lakes.
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 3 of the Five in Five series at Gravesend Cyclopark with 7 hour timed runs on a measured 5.25 mile out and back course and a different coloured medal each day.
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.
An 8.5 km trail loop around Northiam with over 70% off-road running, marshalled course, prizes for top finishers, and tea and cake at Northiam Village Hall; entry limited to 60.
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 off-road 5 mile trail race in Lesnes Abbey Woods with manual timing, a 90-minute cut-off, and awards for the first three men and women.
A roughly 4 mile festive trail run around Pett with a fully marked course, finisher medals, prizes and tea and cake at Pett Village Hall.
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 running, marshals on course and tea and cake afterwards; entry limited to 60 runners.
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.
A multi-terrain 10k, 5k and junior run around Bewl Water on 10 January 2027 with route maps, GPX files, medals and event photography.
A 15 mile multi terrain trail race at Hadleigh Country Park with muddy hills, seaside sections and Thames Estuary views; cupless water stations require a reusable cup.