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Trail Running Calendar near Rochester 2026-2027

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Explore the top trail runs near Rochester for 2026-2027! We've gathered 83 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

September 2026
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.
Timed off road 5 km and 10 km footpath races in Fyfield, Essex supporting the local Scout group with options for a souvenir tee or tree sponsorship.
A 10K run through the private parkland and tree lined avenues of Chevening Estate in Sevenoaks, combining estate heritage, timed results and official 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.
Triple Trail Races 2026 in Kent offers 25km, 50km and 100km trail routes that connect the North Downs Way, Greensand Way and Weald Way, finishing at Loddington Farm with a race village, on-site camping and on-course support.
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.
Ten mile off road trail at Eridge Park with steep climbs, muddy single track, GPX route maps, a finisher memento and cake and a pint at the finish.
Country routes from Wye, Kent offering 27, 20 and 15 mile courses with checkpoints, map based navigation and limited parking near the station.
Point to point runs from Central Park, Dartford along the River Darent with 5K, 10K and 18K options plus a finisher medal and post race refreshments.
October 2026
A 50 km Epping Forest event in London on 03 October 2026, listed as part of Camino Ultra’s 2026 events.
London EcoTrail 25 km is a trail running event in Bell Common, Epping on 03 Oct 2026. It is organised by London based ultramarathon event company Camino Ultra as part of their 2026 events.
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.
A half marathon and 10K through Epping Forest, London on 10 October 2026, run on marked woodland trails with aid stations, chip timing and an eco friendly focus.
A military inspired obstacle mud run at Hever Castle on 10 October 2026 offering 3K, 6K and 12K courses, junior options, and an event village with spectator attractions.
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.
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.
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