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.
October 2026
An overnight self supported 50 km ultra from East Grinstead to Brighton on 30 to 31 October 2026, in person event with tickets at £14.46 and no refunds.
A relaxed night obstacle run at OPP over two 1.5 km laps, with technical obstacles, surprise elements and a strict headtorch requirement.
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
Experience an after dark Halloween themed multi terrain run through Leigh on Sea featuring 10k and 5k routes with chip timing and finisher medals.
Take on flat, scenic laps along the Thames towpath in Walton on Thames with flexible starts and distances from 5 km to ultra. Limited places, aid stations, digital results and medals make this a friendly, festival style challenge.
Muddy obstacle runs in Brentwood, Essex offering 6 km, 12 km and 24 km plus options across farmland, woods and lakes with dozens of natural and man made obstacles.
A riverside marathon and half marathon on 8 November 2026 featuring a two minute silence pause, flat towpath laps, limited places and medals for all participants.
Join a community of runners at Richmond Park for a series of timed races supporting Movember. Enjoy a hilly tarmac course with distances ranging from a kids mini run to a half marathon in a supportive atmosphere.
Experience the longest established trail race in Essex with a self navigated course of 6 or 16 miles starting from a traditional pub in Chelmsford.
An evening 5 km charity trail run in Writtle on 11 November 2026 that donates £2 per entry to Whizz Kidz, with a self guided route and a pub finish.
A flexible Friday running event on a flat 5.3 km out and back course along the Thames offering distances from 5 km to ultra, timed over a seven hour limit with bespoke finishers medals.
Timed multi-lap run on a flat Thames towpath in Walton on Thames with distances from 5 km to ultra, a seven hour limit, flexible one hour start window and finishers medal options.
A Half Marathon and a 10k on Wimbledon Common in London supporting Beder, with a trail marked course, course marshals and an event village offering food, drink and partner goodies.
A 10 km road and riverside run starting and finishing at Kingston Hawker Centre, using chip timing and offering a finisher medal, refreshments and baggage drop. The event supports Kingston Hospital Charity and notes nearby train and local parking o..
Complete as many 5 km laps as possible on a marked trail loop from Peaslake Community Hall, with a 2 km ascent toward Pitch Hill and a downhill return. Solo and three-person team entries are available, with refreshments and prizes included.