Maidstone
Trail Running Calendar near Maidstone 2026-2027
Explore the top trail runs near Maidstone for 2026-2027! We've gathered 58 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
Annual 25 km and 50 km challenge walk, jog or run through Kent, Surrey and Sussex countryside with written route instructions, checkpoints and food included.
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.
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.
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.