Chislehurst
Trail Running Calendar near Chislehurst 2026-2027
Explore the top trail runs near Chislehurst for 2026-2027! We've gathered 177 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
December 2026
A continuous 200 mile winter trail loop around the South of England on the North Downs Way, Vanguard Way, South Downs Way, Wayfarers Walk and St Swithuns Way.
Join the Christmas Jumper Friday Run on 11 December in Walton on Thames for a relaxed rock up and run along the riverside towpath. Pick 5k to ultra, run laps within a 7 hour window and earn a bespoke finisher medal.
A 100 mile winter point to point trail across the South Downs and North Downs from Amberley Museum to Juniper Hall with a 35 hour limit, three aid stations, crew and drop bag support, medical cover and a strict mandatory kit list.
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 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.
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.
January 2027
A challenging 10K trail race on Box Hill with steep climbs, rough trails, a water station at 6 km and a separate children s fun run.
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.
A flexible seven hour time challenge on a signed Thames riverside loop with distances from 3km to 50km, medals, pins and goody bags.
Lap the Thames towpath in Walton-on-Thames with distances from a 5.3 km lap up to ultra plus flexible starts and medal or no medal entry options.
A guided 30 mile trail run from St Martha's Hill exploring the Surrey Hills and Box Hill with an experienced ultra runner and coach. Group pace, recommended 22 miles training, cost £55 and an alcohol free beer may be available.
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.
A 10‑mile and 5‑mile trail challenge at Pippingford Park with 1568 ft of climbing, hard packed forest trails, wide views and bespoke medals.
February 2027
A seven hour time challenge along the River Thames with distances from 3km to 50km, medals and pins, mixed path and trail terrain.