Trail Running Calendar South East (England) 2026-2027

Trail races of 20 km, 10 km and junior 3 km and 5 km run from Cocking Hilltop across the South Downs, with climbs, scenic views and marshalled, waymarked courses under Trail Running Association licence.

A one-lap 10 km trail around Hampton Estate and Puttenham Common with undulating hills, chip timing and bespoke finisher medals; free nearby parking and finish-line refreshments available.

A 50 mile point to point trail run along the North Downs Way from Farnham to Knockholt Pound, with 5,600 ft of ascent, six aid stations and a 13 hour cut off. Pacers and crews are not permitted and finishers receive a medal.

Compton Harriers stage the Compton Downland Challenge on 16 May 2026 with a multi-terrain full marathon (26.8 miles) and a 16 mile route across the Berkshire Downs. The event includes aid stations, a seven hour limit and a hand-thrown finis..

Run through scenic vineyard hills at Denbies Wine Estate in Dorking on 16 May 2026 on a 5.3 km undulating off road loop. Choose as many laps as you like for distances from 5 km up to ultra with flexible start times and limited places.

A measured 10 km cross country run in Priory Park, Reigate on 17 May 2026 with a 250 metre section plus four laps, water stations, first aid and registration on the day. Trophies and a bespoke medal are awarded and the event supports Sport..

Run the scenic loop at Hurtwood Park Polo Club in Cranleigh, Surrey with distances from 5 km to ultra on mostly flat off road trails. Multi lap format and a seven hour time limit suit all paces and every finisher gets a memento.

A community running event in the parish of Deddington offering 5k, 10k and 20k routes on Sunday 17 May 2026. The event is open to all and supports local organisations including the Deddington Primary School PTA, Deddington PFSU and Deddingt..

A three day urban orienteering weekend in Canterbury from 22 to 24 May 2026 featuring a Friday prologue, a city race through historic streets, and sprint races on the University of Kent campus.

City-centre orienteering in Canterbury offering 5k and 5 mile individual time trial races with maps and basic navigation guidance, live results, prizes and on-site refreshments.

Four point to point races across the South Downs National Park on 23 May 2026, with mainly runnable, non-technical trails and a finish at Beachy Head in Eastbourne. Courses are fully marked and supported with regular aid stations.

A multi-distance trail event from Richmond upon Thames to Brighton on 23 to 24 May 2026. Distances include 100 km, 50 km, 25 km and 10 km with marquee rest stops, medical support, GPS tracking and optional camping.

A Surrey trail running event on 23 May 2026 offering 20K, 41K and 62K routes that all finish at Burys Field, Godalming, with marked courses, regular aid stations and an 11 hour cutoff policy.

A single loop trail race in the South Downs National Park starting and finishing in Eastbourne. The 13.5 mile course follows the South Downs Way via Friston Forest, the Seven Sisters and Beachy Head with 2,000 feet of elevation.

Join the Rebellion 10km at Riverwoods, Marlow on 25 May 2026 for a scenic trail run along the Thames including a crossing of Marlow Bridge. Finishers get a medal, a Rebellion beer or non alcoholic alternative and a pint cup.

A single lap 50 km multi terrain ultramarathon around Maidenhead using the Thames Path, Jubilee River and Green Way. The course is fully signed with four checkpoints, chip timing, live tracking and finish area facilities.

A 50 km route along the River Medway from Rochester to Tonbridge, passing three medieval castles and several villages. The course is mainly flat on marked towpaths and trails with three aid stations and a finish on the Tonbridge athletics t..

A scenic, flat 30 km point to point trail along the River Medway from East Farleigh to Tonbridge on 30 May 2026. Towpaths, riverside views, aid stations, live timing and a finisher medal.

Southampton Running Festival on 31 May 2026 offers 5K, 10K, half marathon, a junior race and a charity place option on a multi lap route through Southampton Common with marked kilometres and event marshals.

Guided 13 mile trail run around the Surrey Hills starting in Guildford, featuring the North Downs Way, St Martha's Church and views from Newlands Corner. Group paced event with kit support and an evening option.