Maidstone
Trail Running Calendar near Maidstone 2026-2027
Explore the top trail runs near Maidstone for 2026-2027! We've gathered 64 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
Measured off road 5 kilometre run at Westley Heights Country Park, part of Pitsea RCs seven race Crown to Crown 2026 series with on course safety cover and varied entry rates.
A bi-annual trail race around Bewl Water in Kent offering 10 km, half marathon, marathon and 50 km ultra on wooded trails and quiet lanes.
A charity ultramarathon along the Thames from Upminster to Southend offering 10, 30 and 50 mile routes on mainly tarmac and hard trails. Organised by c2c to raise funds for Prostate Cancer UK with checkpoints and on-course medical support.
A multi-terrain trail race from Rye Sports Centre in East Sussex offering 30k (slightly over 30 km) and 15k routes through the High Weald AONB. The course links historic churches and passes woodlands, orchards, country lanes and coastal views.
A 10 km run through the private parkland of Chevening Estate in Sevenoaks with timed results, finisher medals and official race photography.
A charity trail run from The Zach Willsher Pub in Benfleet offering two undulating routes of about 5.7 miles and 12 miles, with written route instructions and timed entries. Funds raised go to Macmillan and finishers receive a pub voucher.
Experience the historic trails of Kent with 25km, 50km, or 100km races featuring scenic woodlands, castle views, and a festival style race village.
Community fundraising run at Horsted Keynes Recreation Ground with scenic undulating countryside routes in 2.5 km, 5 km and 8.3 km options.
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.
Two days of obstacle racing at Pippingford Park on September 26 to 27, 2026 featuring Sprint, Super, Beast, Ultra, kids races and the British OCR Ultra Championship.
A 10 mile TRA licensed trail race at Eridge Park on 27 September 2026, with steep climbs, muddy terrain, route maps, a finisher memento and a pint and cake at the finish.
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.
Commando Series at Hever Castle on 10 October 2026 features 3K, 6K and 12K military style obstacle courses with age specific entries and an event village.
The Titsey Trail 10k is a community running event held on Sunday, 11th October 2026. Organized by runners for runners, it raises funds for a variety of local charities.