Trail Running calendar near Chessington 2025-2026

The Harewood Forest Trail Race is a spring running event held in the scenic Harewood Forest, located in the heart of the Test Valley near Andover, Hampshire. The race offers challenging yet beautiful undulating trail routes through the forest, providing a rewarding experience for trail runners. Part..

BigWayRound - Winchester is an award-winning, Gold-rated trail running event held at Winchester Rugby Club. The event offers four distances: 14 miles, 19 miles, a marathon, and a 50K ultramarathon, catering to both new and experienced trail runners. The course features stunning views and traverses i..

The Goring Gap Trails event, held in Mapledurham near Reading, offers a variety of running and walking challenges, including a 50-mile ultra, a 52K ultra, and a half marathon, alongside walking options of half marathon, full marathon, and a 6-mile walk featuring a river boat crossing. The event is l..

The Collingbourne Races, held at Crawlboys Farm in Ludgershall, offer a scenic off-road running experience through the beautiful Collingbourne woods. Featuring a half marathon and a 10km race, the course includes bridle paths, woodland tracks, and single-track trails, making it suitable for runners..

The Run to the Sea Brighton Ultramarathon is a scenic 50km point-to-point race from Horsham to Brighton seafront, featuring a mix of trails and rolling downs. Known for its stunning views and well-organized setup, it caters to both beginners and experienced ultramarathoners. The course is fully sign..

The Chiltern Hills 100K is a 100-kilometer ultra marathon held in the Chiltern Hills, Buckinghamshire, UK. The race features an anticlockwise loop starting and finishing in Chesham, passing iconic landmarks such as Ashridge Estate, Coombe Hill, Whiteleaf Hill, Bledlow Ridge, and Great Hampden. With..

Shires and Spires is a renowned multi-terrain running event held in Northamptonshire, UK, starting and finishing at Naseby Village Hall. The race offers five distances: 10K (road), half marathon, three-quarter marathon, marathon, and a challenging 35-mile ultra marathon. The course features a scenic..

The Zig Zag Marathon and Half Marathon take place at the Suffolk Running Centre in Bury St Edmunds, UK. The marathon follows the officially measured, scenic Kirtling Route, which is fully on road and mildly undulating, while the half marathon uses the Windmill Route, both consisting of single loops...

The Halstead & Essex Marathon, held annually in North Essex, celebrates its 30th year in 2026. Established in 1995, the event is hosted by Halstead Road Runners and attracts runners from across the UK. The marathon course features scenic, low-traffic roads through rolling hills, woods, and farmlands..

The Centurion North Downs Way 50® is a challenging 50-mile point-to-point ultramarathon held annually along the North Downs Way National Trail in England. Starting in Farnham, Surrey, and finishing at Knockholt Pound near Greater London, the course features approximately 5,600 feet of elevation gain..

The Reigate Priory Park 10K is a scenic charity fun run held in Priory Park, Reigate, Surrey. The course features a 250-meter start plus four laps on an accurately measured, gently undulating cross-country terrain surrounded by lush greenery. Suitable for runners of all levels, the event fosters a f..

The South Downs 50k is a point-to-point trail race held in the South Downs National Park, running from Falmer to Eastbourne along the scenic South Downs Way. Covering 50 kilometers with over 3,500 feet of elevation gain and descent, the course features mostly runnable grass trails, farm tracks, and..

Farmmageddon is an endurance running event held at Hyde Hall Farm, Buntingford (SG9 0RU), returning for its second year in May 2026. The main challenge is a 100-mile race completed over 32 hours, featuring a 5.3 km loop course that includes trail, grassland, and some tarmac paths. The event offers m..

The London 2 Brighton Ultra Challenge is a premier endurance event held annually, covering distances of 100km, 50km, 25km, and 10km. Starting in Richmond, West London, participants traverse the scenic North Downs and Surrey & Sussex countryside, with the full 100km route continuing over the South Do..

The The Fox Trail will take place in Guildford on Saturday 23 May 2026. You can run between 20 and 62 kilometers.

The Seven Sisters Half Marathon is a scenic 13.5-mile trail race held in the South Downs National Park, starting and finishing at Helen Garden in Eastbourne. The course follows the South Downs Way, passing through Friston Forest, woodland trails, the iconic Seven Sisters cliffs, and Beachy Head, off..

The Castle Trails 30km is a scenic point-to-point trail race in Kent, launching in 2026 as part of the Three Castles 50km Ultra weekend. Starting at Little Fant Farm near Maidstone and finishing in Tonbridge, the course follows the River Medway, passing historic sites like East Farleigh’s stone brid..

The Three Castles 50km Ultra Marathon is a scenic race held in Kent, England, starting in Rochester and finishing at Tonbridge athletics track. The flat course follows the River Medway, passing three medieval castles, charming villages, and lush countryside along the Medway Valley Walk. Runners expe..

The Ridgeway Challenge is an 86-mile (139 km) point-to-point trail running race along the entire length of The Ridgeway National Trail in England. Starting at Ivinghoe Beacon in Hertfordshire and finishing at the Avebury Stones in Wiltshire, the course follows a historic path over 5,000 years old. T..

The Beat the Sunset 50km is a multi-terrain ultramarathon held in the Thames Valley, starting and finishing at Summerleaze Park in Maidenhead, Berkshire. The flat, single-lap course covers 50 kilometers with 235 meters of elevation, featuring 75% off-road trails along the Thames Path, Jubilee River,..