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 199 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
December 2026
Trail 5K and 10K around the Tewinbury estate in Hertfordshire, fully waymarked with marshals, aid station at 5.3 km and chip timing.
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.
A 200 mile continuous winter trail loop from Juniper Hall around southern England on the North Downs Way, Vanguard Way and South Downs Way with a 96 hour limit.
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.
Mince Pi Run on 13 December 2026 at Shalford Park, Guildford offers looped offroad races from 3.14 to 31.4 miles, a Pi marathon option and a one mile fun run shaped like the Pi symbol. The course runs along the water and results are posted online.
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 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.
Looped trail and road races near Chalfont St Peter offering 7K and 10K loops with distance choices up to ultramarathons plus aid stations and medical support.
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.