Trail Running calendar near London Borough of Enfield 2026-2027

A seven hour Time Challenge along the River Thames at Wraysbury Skiff and Punting Club in Egham, with distances from 3 km up to 50 km. Finishers receive a Christmas themed medal, distance pins for half marathon and above, and a goody bag.

A cupless charity run through Rathfinny Wine Estate on 28 December, comprising two 5 km vineyard loops with limited places and a donation of £8 from each £12.50 entry to the WOLO Foundation.

Winter Runderland in Walton on Thames is a timed lap event on a 5.3 km riverside towpath course. Runners may select distances from 5 km up to ultra, and a lower-cost no-medal entry option is available.

A January trail race around Box Hill with a measured 10.000 km course, 473 m ascent and 335 m descent. Registration and parking at Denbies Vineyard; earphones are not permitted and an alternative Denbies course is used if Box Hill is closed..

Join the Penshurst Village Cross Country Run on Sunday 3 January 2027 for challenging 5 mile and canicross races over scenic local trails and open ground. Enjoy a friendly village atmosphere and a great day out for runners and their dogs.

A 43 mile point to point ultra from Wendover to Little Venice, London, mixing country trails and Grand Union Canal towpath. The race includes GPS tracking, five checkpoints, baggage transfer, mandatory kit and an 11 hour cutoff.

A timed lap event along the Thames towpath combining running and a doughnut theme. Participants choose how many 5.3 km laps to run, receive a bespoke finisher medal, and can take part attended or virtually.

A countryside trail run around Farley Mount in Hampshire with two route options, including a Half Marathon. The course is rolling with tree-lined sections and vistas, starts at Sparsholt College with ample parking, and offers finisher medal..

A looped timed event at Brandon Country Park with a 5.3 km multi terrain lap. Runners choose a four hour or six hour option, use a base camp aid station each lap, and receive a finisher medal.

A multi-distance road event on 16 January 2027 from Suffolk Running Centre offering 5k to ultra options, rolling hills and village scenery. Aid stations appear every 10k and a bespoke finisher medal is provided.

A 15 mile multi-terrain trail run at Hadleigh Country Park featuring muddy, undulating sections and elevated Thames Estuary views. Route maps and GPX files are available and the event operates a cupless water policy.

The Ashdown Forest 10 Mile will take place in Wych Cross on Sunday 31 January 2027. You can run between 5 and 10 miles.

A fully signed trail ultra on the North Downs Way and Norbury Park, covering 50k with 2986 ft ascent. The event is based at Denbies Wine Estate, includes four checkpoints with food and drink, and awards a finisher medal.