City of London
Trail Running Calendar near City of London 2026-2027
Explore the top trail runs near City of London for 2026-2027! We've gathered 222 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
October 2026
A lap based Friday timed run on a flat 5.3 km out and back course along the river Thames, with distances from 5 km up to ultra. Both attended and virtual entrants receive a finisher medal.
Annual 25 km and 50 km challenge walk, jog or run through Kent, Surrey and Sussex countryside with written route instructions, checkpoints and food included.
A guided 10 miles through the Chilterns along canals, reservoirs and past Britain’s oldest post windmill, with trail instruction and a finisher’s medal included.
A night time closed road 10K in East London from Silverworks Island through the Royal Docks and London City Airport runway, women focused and currently sold out.
Timed multi-lap running at Buchan Country Park in Crawley with lap based distances from 5 km up to ultra, flexible start times and a seven hour time limit. Medal and lower cost no medal entry options are offered.
Timed, self supported anti clockwise loop around Canvey Island starting and finishing at Waterside Farm Leisure Centre, with a pub check point about 10k in and a four hour cut off.
A 7 hour Time Challenge along the River Thames in Staines offering distances from 3 km up to 50 km, themed medals and distance pins, an aid table, goody bags including a vegan option, and on the day number collection.
A charity tower climb at 22 Bishopsgate, London covering 58 floors and over 1,500 steps with a fundraising target and included t-shirt and medal.
A flat 30 mile out and back ultra along the River Stort with checkpoints about every 5 miles, electronic timing, finishers medal and trophies for top three men and women.
Looped events where runners choose how many laps to run on the day, with maps, aid stations every lap and distances from 5K to 50K across several venues.
Halloween themed night trail at Langdon Nature Discovery Park with a 5k for ages 12 and over and a free 800m Little Monsters children's trail.
A 7 hour time challenge along the River Thames in Staines with flexible distances, chooseable medals, on course aid and goody bags.
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 Halloween-themed 3 km obstacle run on a new course with waves of participants, mandatory headtorch, on-course burpee penalties, and optional costumes.
A single-loop 50K trail race from Berkhamsted through The Ridgeway and Ashridge, with 800 m ascent, fully marked navigation and three on-route aid stations.
A Halloween brewery trail run in Chelmsford with a devilish 6.66 km route, fancy dress rules, a finishers medal and limited places.