Trail Running calendar near Chesham 2026-2027

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 lapped timed run at Brandon Country Park with four hour and six hour options. Runners complete repeated 5.3k laps on gravel and grass to reach 5k, 10k, half, full or ultra distances.

A road event around Bury St Edmunds using the Windmill Way route and Golding Hills. Distances from 5k to ultra, rolling hills, aid stations every 10k, parking included and a bespoke finisher medal.

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 May Hill Massacre will take place in Longhope on Saturday 30 January 2027.

A 10 miles and 5 miles trail race at Pippingford Park Manor with hard packed trails, about 1568 ft of climbing and panoramic views. The event includes bespoke medals, cash prizes for podium finishers and free parking.

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.