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.
September 2026
A timed lap event in Crystal Palace Park where runners complete 2.65 km laps within a seven hour limit, choosing distances from 5 km to ultra. The off road course mixes tarmac and gravel and all participants receive a bespoke finishers medal.
A five mile trail run on 24 September 2026 at The Viper in Mill Green near Ingatestone. Limited to over 18s with a small field; participants must be self sufficient with phone and headtorch and a tail runner is on course.
Obstacle course weekend at Pippingford Park on 26–27 Sep 2026 with Sprint, Super, Beast, Ultra, Kids races and the British OCR Ultra Championship.
A 10 mile, traffic free trail run at Eridge Park on 27 September 2026 featuring steep climbs, muddy sections, route maps and finish-line cake and a pint.
October 2026
A 50 mile coastal ultramarathon along the Essex saltmarshes, starting at South Woodham Ferrers Rugby Club and finishing at Maldon Promenade Park. Fully supported with aid stations, GPX route files, a shuttle option and a 15 hour cut off.
A community organised 10 km race at Imberhorne School featuring mixed terrain, marshals, chip timing and a sustainably sourced finisher medal supporting local charities.
Looped trail event near Maidstone offering 50 km, 25 km and 10 km options. The route follows the North Downs Way and River Medway and includes covered rest stops, GPS tracking and camping at basecamp.
Military style obstacle mud run at Hever Castle Kent with 3 km, 6 km and 12 km options and many obstacles modelled on Royal Marines training.
A single lap 10k through Oxted Woodlands on off road tracks and footpaths, with varied slopes, a water station and finishers' 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.
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, a 60 person entry limit, prizes for first male and female, and tea and cake after the race.
A timed self supported anti clockwise loop around Canvey Island starting and finishing at Waterside Farm Leisure Centre with a staffed pub check at 10 km.
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.
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.