Trail Running calendar near Woking 2026-2027

A guided trail run on Box Hill that gains about 1000 m over 12.5 miles, featuring technical climbs, scrambling and varied terrain. Group paced for sustained trail running ability with parking at Stepping Stones Car Park.

Choose 10 Mile or 10K starting at Hengistbury Head and run Bournemouth seafront via Boscombe Pier on largely flat, traffic free paths with sea views. Chip timed and marshalled, the event offers water, post race treats and a medal for finish..

Trail races in Swanage along the Jurassic Coast Path with 10K, half, marathon and ultra distances, electronic timing and fully marked courses. Optional coach transport is available and standard entry terms include a 30 day refund window.

A single loop 55 mile trail race around the South Downs, starting and finishing at Plumpton Racecourse. The route covers grass trails, farm tracks and woodland paths, includes 7,000 ft of ascent and seven aid stations.

A **50 km** trail ultramarathon from Dorking along the Greensand Way into the Surrey Hills, featuring a 5 mile loop and climbs over Leith Hill, Holmbury Hill and Pitch Hill. The route is fully signed, supported and electronically timed.

A seasonal ten mile multi terrain race in Peacehaven with farm tracks, quieter roads and a notable hill around mile six. The event includes fancy dress, recycled finisher medals, charity partners and photos supplied by Sussex Sports Photogr..

New Forest Xmas Trails offers festive trail races from Holmesly Campsite in the New Forest. Distances range from 15 km to a 50 km ultramarathon on fully marked heath and woodland trails; opt to plant a tree instead of a medal.

A 10 mile loop around Grafham Water starting on the dam, offered as a standard run and a canicross. Scenic reservoir views, woodland trails, finisher medals, on site camping and options for dog friendly entries.

A 200 mile continuous trail run looping around the South of England from Juniper Hall. Runners have up to 96 hours, live tracking, and access to three major aid stations with crew support and drop bags.

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.

Join the Mince Pi Run in Guildford for a Pi themed run by the water, with distances from a 1 mile kids fun run to the 3.14 mile loop and laps up to a Pi marathon. Every finisher gets a bespoke Pi Pie medal.

Salcey Forest Christmas Race offers flat but muddy tree lined trails for 5k and 10k plus a junior fun run. Seasonal fancy dress is encouraged with a best outfit prize, and proceeds support Shelter.

A 10 mile cross country run through the West Wight landscape on 13 December 2026, with hilly terrain, strong marshal support and a memento for finishers. Entry is limited and the published fee is £27.50.

Join the 20th Christmas Pudding Dash near Pett, Hastings for a festive muddy cross country with a looped main race of about 4.2 miles plus a fun run and children's scurry. Enjoy medals, photos, fancy dress prizes and support for Shelter.

Celebrate Christmas Eve with the Die Hard Christmas races around scenic Caldecotte Lake in Milton Keynes, with marathon and half marathon options. Enjoy lakeside laps, friendly race support and a bespoke finisher medal.

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.