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.
November 2026
Experience an after dark Halloween themed multi terrain run through Leigh on Sea featuring 10k and 5k routes with chip timing and finisher medals.
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 approx 8.5 km loop trail around Northiam on 29 November 2026 with over 70% trail, a 60 person entry limit, prizes and post race tea and cake at the village hall.
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 roughly 4 mile trail run around Pett on 19 December 2026 with a marshalled, fully marked course, Christmas finisher medal, prizes and post-race tea and cake.
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.
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.
New Year running event at Bewl Water on 10 January 2027 offering 10k, 5k and a junior run on undulating multi terrain with reservoir views.
A 10‑mile and 5‑mile trail challenge at Pippingford Park with 1568 ft of climbing, hard packed forest trails, wide views and bespoke medals.
February 2027
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 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.
Nuclear Rush is a May obstacle race at the Secret Nuclear Bunker Estate in Essex offering 6 km and 12 km courses with 40+ and 70+ obstacles, plus family and kids races.
Off road 10 km, 5 km and family runs at Milton Creek Country Park on 9 May 2027 supporting The Oliver Fisher Special Care Baby Trust. Varied trail terrain, route maps and event medals are provided.