Maidstone
Trail Running Calendar near Maidstone 2026-2027
Explore the top trail runs near Maidstone for 2026-2027! We've gathered 60 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A single lap 10 km trail race through Limpsfield Common and the High Chart, mostly off-road with varied slopes, a water station at about 5.5 km, and finisher T-shirt and medal.
A single-lap 10K on 11 October 2026 around Burnham on Crouch, featuring sea wall coastal paths and countryside trails. The event is based at Dengie Hundred Sports Centre with free parking, facilities and post-run food and drink.
An annual 25 km or 50 km countryside challenge in Kent Surrey and Sussex with written route directions, checkpoints, included food and GPX files.
A night time closed road 10K in East London from Silverworks Island through the Royal Docks and London City Airport runway, women focused and currently sold out.
Trail races at Bedgebury National Pinetum & Forest on 18 October 2026, offering half marathon, 10 km and junior distances on traffic free woodland trails.
A 10 km trail run through the private grounds of Hole Park, a historic estate near Cranbrook, Kent, on 18 October 2026. Entry is priced at £25 and the event includes timed results, finisher medals and official race photography.
An 8 km trail loop around Herstmonceux with over 70% trail, prizes for first male and female, village hall facilities and a 60 person entry limit.
Timed, self supported anti clockwise loop around Canvey Island starting and finishing at Waterside Farm Leisure Centre, with a pub check point about 10k in and a four hour cut off.
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 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 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.
An 8.5 km mostly trail loop around Northiam with a marked and marshalled course, prizes for first male and female, and entry limited to 60 runners.
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 4 mile trail run around Pett on 19 December 2026 with a marshalled, fully marked muddy course, Christmas finisher medals, 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.