Rochester
Trail Running Calendar near Rochester 2026-2027
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.
October 2026
Annual 25 km and 50 km routed challenge across Kent, Surrey and Sussex with checkpointed support, food included and GPX route files provided.
Forest trail races at Bedgebury National Pinetum in October offering a half marathon, a 10K and a junior race with route maps, photos and limited free parking.
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.
A timed, self supported anticlockwise loop around Canvey Island starting and finishing at Waterside Farm Leisure Centre. The mostly coastal route includes sea wall, grass and gravel paths, a 10k pub check point and a four hour cut off.
Trail marathon and half marathon near Canterbury through Kentish countryside; marathon requires navigation and both races use CCCU Sports Centre as HQ.
A countryside walking event from Blackmore with a 26 mile figure of eight route and an 18 mile option, forming part of the Essex and Herts Triple Challenge.
A Halloween themed 6.66 km trail run in Chelmsford on 31 October 2026 with GPX/Strava route support, fancy dress prizes and a brewery finish offering a medal, drink and crisps.
November 2026
An after dark multi terrain 10 km and 5 km event in Leigh on Sea with chip timing, mandatory headtorches and sustainably sourced finishers medals.
A November muddy obstacle event in Essex offering 6 km, 12 km and 24 km+ courses with natural and man‑made obstacles including a Deathslide and zip wire.
A mostly off road 15k at Trifarm, Boreham, run on public footpaths and bridleways with on-site parking, water refill points and manual timing.
December 2026
A social 12k at Chelmsford Brewery with a GPX and Strava route, checkpoint drinks and Christmas medals, plus encouraged fancy dress.
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.
Final round of the four-event Trifarm Winter series: a mainly off-road 10 km on public footpaths and bridleways at Trifarm in Boreham on 27 December 2026.
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.
Running at Bewl Water on 10 January 2027 with 10k, 5k and a junior run on multi terrain routes beside the reservoir; maps and GPX files are provided.
February 2027
Trail races of 10 Mile, 5 Mile and a junior run take place in Bedgebury National Pinetum & Forest on 7 February 2027. The undulating multi terrain courses can be muddy after wet weather and include a bespoke medal and free photos.
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 42-mile trail race from Chipping Ongar to the ancient Chapel of St Peter-on-the-Wall, following an old pilgrimage route through rural Essex. Mostly off-road and often muddy, the route is waymarked with GPX support, four outdoor checkpoints and mand..