Chislehurst
Trail Running Calendar near Chislehurst 2026-2027
Explore the top trail runs near Chislehurst for 2026-2027! We've gathered 173 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
November 2026
A charity Friday run in Walton on Thames where the £10 entry fee is donated to Rays of Sunshine. Flexible rock up and run format on a flat 5.3 km riverside lap with a finishers' medal for all participants.
A riverside marathon and half marathon along the River Thames on an accurately measured UKA certified course. Multiple laps on a flat towpath route with medals for all finishers and virtual entries.
Join the Christmas Advent Run on Sunday 29 November in Walton on Thames for a festive riverside run. Tackle timed laps to suit you and enjoy optional medal and chocolate advent calendar plus a prize draw.
December 2026
Trail 5K and 10K at Tewinbury, Hertfordshire, on undulating dirt, grass and woodland trails with marshals, chip timing and an aid station.
Timed Thames towpath run where participants choose lap distances on a 5.3 km out and back course and entry supports Rays of Sunshine Children's Charity.
A guided 12.5 mile trail run around Box Hill that gains about 1000 metres of elevation across woodland, heathland and open fields. Group pace with technical climbs and scrambling and a chance of an alcohol free beer at the finish.
Timed lap event at Tilgate Park, Crawley with 5 km laps and distances from 5 km to ultra, a 7 hour limit, and a finisher medal for all participants.
A 200 mile continuous winter trail adventure forming a giant loop across the south of England with a 96 hour time limit and 22500 feet of elevation.
A Christmas timed run along the Thames in Walton on Thames with lap-based distances from a 5.3 km loop up to ultra and medal or no medal entry options.
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.
Join a festive Christmas run along the flat Jubilee River. Choose your own distance in this 6-hour timed event on a scenic towpath. All finishers receive a bespoke festive medal.
A dawn to dusk trail challenge at Box Hill where runners complete laps of a roughly 10 mile loop with about 2,400 ft ascent per lap; entries include insurance, medical cover and a finisher medal.
A festive 12 km run in Chelmsford with a brewery checkpoint, post-run drinks at the Voodoo Keller Bar, GPX/Strava route and Christmas medals for all finishers.
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 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.
A low key multi-lap half and full marathon along the River Thames in Walton on Thames on 28 December 2026. The UKA certified flat towpath course awards medals to all finishers and has limited places.